CA2015996C - Bis-(1h-indol-3-yl)-maleinimide derivatives and their use as pharmaceuticals - Google Patents
Bis-(1h-indol-3-yl)-maleinimide derivatives and their use as pharmaceuticals Download PDFInfo
- Publication number
- CA2015996C CA2015996C CA002015996A CA2015996A CA2015996C CA 2015996 C CA2015996 C CA 2015996C CA 002015996 A CA002015996 A CA 002015996A CA 2015996 A CA2015996 A CA 2015996A CA 2015996 C CA2015996 C CA 2015996C
- Authority
- CA
- Canada
- Prior art keywords
- indol
- maleinimide
- hydroxy
- propyl
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Image Processing (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Aerodynamic Tests, Hydrodynamic Tests, Wind Tunnels, And Water Tanks (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The present invention provides bis-(1H-indol-3-yl)-maleinimide derivatives and the pharmacologically acceptable salts thereof, processes for the preparation of these compounds and pharmaceutical compositions containing them for the treatment of heart and blood vessel diseases, such as thromboses, arteriosclerosis, hypertension of inflammatory processes, allergies, cancer and certain degenerative damages of the central nervous system, as well as of diseases of the immune system and viral diseases. The maleinimide derivatives of the invention are of formula I
Description
DESCRIPTION
The present invention is concerned with new bis-(1H-indol-3-yl)-maleinimide derivatives of the general formula I, H
~i R' R 5 (I) R. R a wherein R1 and R2, which can be the same or different, are hydrogen atoms, straight-chained or branched alkyl radicals containing up to 18 carbon atoms, benzyl radicals which are unsubstituted or substituted with up to three C1-C4-alkyl radicals, C1-C4-alkoxy radicals or halogen atoms, aminoalkyl radicals containing up to 12 carbon atoms which are unsubstituted on the nitrogen atom or mono- or disubstituted on the nitrogen atom by benzyl radicals or C1-C4-alkyl radicals or in which the substituents, together with the nitrogen atom, form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, a hydroxyl group or a C1-C4-alkoxy radical, an amidinothioalkyl radical containing up to 12 carbon atoms, a nitroguanidinoalkyl radical containing up to 12 carbon atoms, an isothiocyanatoalkyl radical containing up to 12 carbon atoms, epoxyalkyl radicals containing up to 6 carbon atoms, alkoxycarbonylalkyl radicals containing up to 6 carbon atoms, -CHZ-CO-NRllRia radicals, wherein R11 and R12 can be the same or different and are hydrogen atoms, alkyl radicals containing up to 6 carbon atoms or benzyl radicals, haloalkyl or hydroxyalkyl radicals which can R~ R2 optionally be substituted by a halogen atom or a hydroxyl group, or alkoxyalkyl radicals, optionally substituted by up to 3 hydroxyl groups, and containing, in each case, up to 6 carbon atoms, acyl radicals containing up to 4 carbon atoms or glycoside radicals, R4, R5, RS and R9 and, independently of one another, are hydrogen or halogen atoms, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-acyloxy radicals, nitro groups or amino groups which are unsubstituted or mono- or disubstituted by benzyl radicals or C1-C4-alkyl radicals, benzyloxy radicals, hydroxyl groups, aminoalkoxy radicals containing up to 12 carbon atoms which, on the nitrogen atom, can be unsubstituted or mono- or disubstituted by benzyl radicals or C1-C4-alkyl radicals or in which the substituents, together with the nitrogen atom, can form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, a hydroxyl group or a C1-C4-alkoxy radical or trifluoromethyl radicals or two neighbouring substituents can together represent a methylenedioxy radical, with the proviso that not all of the symbols R1 to R9 are hydrogen atoms or, when R4 or R4 and R9 are hydroxyl groups, all the other symbols do not signify hydrogen atoms; and the pharmacologically acceptable salts thereof as well as pharmaceutical compositions containing at least one of a compound of formula I.
Compounds of general formula I are preferred in which R1 and R2 are the same or different and signify hydrogen atoms, straight-chained or branched alkyl radicals containing up to 4 carbon atoms, aminoalkyl radicals containing up to 4 carbon atoms in the alkyl moiety which can be substituted on the alkyl moiety by alkoxy radicals containing up to 4 carbon atoms or by hydroxyl groups and which, on the nitrogen atom, can be unsubstituted or mono- or disubstituted by alkyl radicals containing up to 4 carbon atoms or in which the substituents, together with the nitrogen atom, form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, and R4, R5, Ra and R9, independently of one another, are hydrogen or halogen atoms, C1-C4-alkyl, C1-C4-alkoxy, benzyloxy, hydroxyl, aminoalkoxy containing up to 4 carbon atoms in the alkyl moiety which can be substituted on the alkyl moiety by C1-C4-alkoxy radicals and which, on the nitrogen atom, are unsubstituted or mono- or disubstituted by C1-C4-alkyl radicals or in which the substituents, together with the nitrogen atom, form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, or two neighbouring symbols R4, R5, R8 and R9 together signify a methylenedioxy radical.
Also preferred are bis-(1H-indol-3-yl)-maleinimides of general formula I in which R1 and/or R2 are hydrogen atoms or methyl, ethyl, n-propyl, isopropyl, n-butyl, benzyl, acetyl, methoxycarbonylmethyl, 2-methoxyethyl, 2-aminoethyl, 3-aminopropyl, 1-amino-2-propyl, 2-dimethylaminoethyl, 3-dimethylamino-1-propyl, 3-dimethylamino-2-propyl, 2-diethylaminoethyl, 2-(N-benzyl-N-methylamino)-ethyl, 3-(N-benzyl-N-methylamino)-propyl, 3-dimethylamino-2-hydroxy-1-propyl, 2-piperidinoethyl, 3-piperidinopropyl, 2-pyrrolidinoethyl, 3-pyrrolidinopropyl, 2-morpholinoethyl, 3-morpholinopropyl, pyrrolidin-2-ylmethyl, N-methylpyrrolidin-2-yl-methyl, glucosyl, rhamnosyl, ribosyl, deoxyribosyl, aminoglycosyl, 3-hydroxypropyl, 2-carboxyethyl, 2-dimethylaminoethylcarbonyl, dimethylaminomethylcarbonyl, 2-hydroxyethoxymethyl, (2-hydroxy-1-hydroxymethyl)-ethoxymethyl or (3-hydroxy-1-hydroxymethyl)-propoxymethyl radicals and RS
and/or Ra are hydrogen, chlorine, bromine or fluorine atoms or trifluoromethyl, methyl, ethyl, hydroxyl, benzyloxy, methoxy, amino, dimethylamino, 2-aminoethoxy, 3-aminopropoxy, 1-amino-2-propoxy, 2-dimethylaminoethoxy, 3-dimethylamino-1-propoxy, 5 3-dimethylamino-2-propoxy, 2-diethylaminoethoxy, 2-[N-benzyl-N-methylamino]-ethoxy, 3-[N-benzyl-N-methylamino]-propoxy, 3-dimethylamino-2-hydroxy-1-propoxy, 2-piperidinoethoxy, 3-piperidinopropoxy, 2-pyrrolidinoethoxy, 3-pyrrolidinopropoxy, 2-morpholinoethoxy, 3-morpholinopropoxy, 2-piperazinoethoxy, 3-piperazinopropoxy, pyrrolidin-2-ylmethoxy or N-methylpyrrolidin-2-ylmethoxy radicals or R4 and RS and/or R8 and R9 together represent a methylenedioxy radical.
The present invention is also concerned with the use of compounds of general formula I, including compounds in which R1 to R9 are hydrogen atoms or in which R4 or R4 and R9 are hydroxyl groups and the other symbols R1 to R9 are hydrogen atoms, for the preparation of pharmaceutical compositions for the prevention or treatment of diseases in which the inhibition of protein kinase C is of importance.
The present invention also provides pharmaceutical compositions which, in addition to conventional adjuvant and additive materials, contain at least one compound of general formula I, including compounds in which R1 to R9 are hydrogen atoms or in which R4 or R4 and R9 are hydroxyl groups and the other symbols R1 to R9 are hydrogen atoms.
The preparation of the compounds of general formula I
takes place analogously to the processes described in the literature (Tetrahedron, 44, 2887/1988; Tetrahedron Lett., 1985, 4015; European Patent Specification No. 0 269 025) or with the use of appropriate variations of these processes. The process according to the present invention is characterised in that either A) a dibromomaleinimide of the general formula II, Z
I
N
~- O
(II) Br Br in which Z is an appropriate protective group which can be split off, is reacted in known manner with an indole Grignard reagent of the general formula (A) R$
Rg' \ N
I
Mg Hal in which Ra and R9 have the above-given meanings except that they are not hydroxyl groups or acyloxy radicals, and the product obtained of the general formula III, Z
I
N
-O
R$
/ \Br (III) R9 \ N~
R' in which Rl is a hydrogen atom, is optionally alkylated in known manner on the indole nitrogen atom with an alkylation agent of the general formula R1-X, in which R1 has the same meaning as above with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions and X is a group which is easily removed, such as a chlorine or bromine atom, to give a compound of general formula III in which R1 is other than a hydrogen atom and subsequently the product of general formula III is reacted with an indole Grignard reagent of the general formula (B), i I
Mg Hal in which R4 and RS have the above-given meanings except that they are not hydroxyl groups or acyloxy radicals, and optionally subsequently alkylated with an alkylation agent of the general formula R2-X in which X has the above-given meaning and RZ has the above-given meaning with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions, to give a compound of the general formula IV, Z
I
O~N~-=p Rs ~ ~ ~ ~ ,R5 (IV) 3 0 Rs~ ~N~~Ra N
R' R2 whereafter the substituted imide group is converted into an unsubstituted imide group of general formula I; or B) a compound of the general formula V, Z
I
O
R:
(V) R' I
Y
in which Y and Z are appropriate protective groups which can be split off, is reacted with an indole Grignard reagent of the general formula (B), ( R4 \ N
I
Mg Hal in which R4 and RS have the above given meanings except that they are not hydroxyl groups or acyloxy radicals, and subsequently optionally alkylated with an alkylation agent of the general formula R2-X in which X has the above-given meaning and RZ has the above-given meaning with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions, to give a compound of the general formula VI
The present invention is concerned with new bis-(1H-indol-3-yl)-maleinimide derivatives of the general formula I, H
~i R' R 5 (I) R. R a wherein R1 and R2, which can be the same or different, are hydrogen atoms, straight-chained or branched alkyl radicals containing up to 18 carbon atoms, benzyl radicals which are unsubstituted or substituted with up to three C1-C4-alkyl radicals, C1-C4-alkoxy radicals or halogen atoms, aminoalkyl radicals containing up to 12 carbon atoms which are unsubstituted on the nitrogen atom or mono- or disubstituted on the nitrogen atom by benzyl radicals or C1-C4-alkyl radicals or in which the substituents, together with the nitrogen atom, form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, a hydroxyl group or a C1-C4-alkoxy radical, an amidinothioalkyl radical containing up to 12 carbon atoms, a nitroguanidinoalkyl radical containing up to 12 carbon atoms, an isothiocyanatoalkyl radical containing up to 12 carbon atoms, epoxyalkyl radicals containing up to 6 carbon atoms, alkoxycarbonylalkyl radicals containing up to 6 carbon atoms, -CHZ-CO-NRllRia radicals, wherein R11 and R12 can be the same or different and are hydrogen atoms, alkyl radicals containing up to 6 carbon atoms or benzyl radicals, haloalkyl or hydroxyalkyl radicals which can R~ R2 optionally be substituted by a halogen atom or a hydroxyl group, or alkoxyalkyl radicals, optionally substituted by up to 3 hydroxyl groups, and containing, in each case, up to 6 carbon atoms, acyl radicals containing up to 4 carbon atoms or glycoside radicals, R4, R5, RS and R9 and, independently of one another, are hydrogen or halogen atoms, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-acyloxy radicals, nitro groups or amino groups which are unsubstituted or mono- or disubstituted by benzyl radicals or C1-C4-alkyl radicals, benzyloxy radicals, hydroxyl groups, aminoalkoxy radicals containing up to 12 carbon atoms which, on the nitrogen atom, can be unsubstituted or mono- or disubstituted by benzyl radicals or C1-C4-alkyl radicals or in which the substituents, together with the nitrogen atom, can form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, a hydroxyl group or a C1-C4-alkoxy radical or trifluoromethyl radicals or two neighbouring substituents can together represent a methylenedioxy radical, with the proviso that not all of the symbols R1 to R9 are hydrogen atoms or, when R4 or R4 and R9 are hydroxyl groups, all the other symbols do not signify hydrogen atoms; and the pharmacologically acceptable salts thereof as well as pharmaceutical compositions containing at least one of a compound of formula I.
Compounds of general formula I are preferred in which R1 and R2 are the same or different and signify hydrogen atoms, straight-chained or branched alkyl radicals containing up to 4 carbon atoms, aminoalkyl radicals containing up to 4 carbon atoms in the alkyl moiety which can be substituted on the alkyl moiety by alkoxy radicals containing up to 4 carbon atoms or by hydroxyl groups and which, on the nitrogen atom, can be unsubstituted or mono- or disubstituted by alkyl radicals containing up to 4 carbon atoms or in which the substituents, together with the nitrogen atom, form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, and R4, R5, Ra and R9, independently of one another, are hydrogen or halogen atoms, C1-C4-alkyl, C1-C4-alkoxy, benzyloxy, hydroxyl, aminoalkoxy containing up to 4 carbon atoms in the alkyl moiety which can be substituted on the alkyl moiety by C1-C4-alkoxy radicals and which, on the nitrogen atom, are unsubstituted or mono- or disubstituted by C1-C4-alkyl radicals or in which the substituents, together with the nitrogen atom, form a heterocyclic ring containing 3 to 6 carbon atoms, wherein the alkyl chain can be substituted by further C1-C4-alkyl radicals, or two neighbouring symbols R4, R5, R8 and R9 together signify a methylenedioxy radical.
Also preferred are bis-(1H-indol-3-yl)-maleinimides of general formula I in which R1 and/or R2 are hydrogen atoms or methyl, ethyl, n-propyl, isopropyl, n-butyl, benzyl, acetyl, methoxycarbonylmethyl, 2-methoxyethyl, 2-aminoethyl, 3-aminopropyl, 1-amino-2-propyl, 2-dimethylaminoethyl, 3-dimethylamino-1-propyl, 3-dimethylamino-2-propyl, 2-diethylaminoethyl, 2-(N-benzyl-N-methylamino)-ethyl, 3-(N-benzyl-N-methylamino)-propyl, 3-dimethylamino-2-hydroxy-1-propyl, 2-piperidinoethyl, 3-piperidinopropyl, 2-pyrrolidinoethyl, 3-pyrrolidinopropyl, 2-morpholinoethyl, 3-morpholinopropyl, pyrrolidin-2-ylmethyl, N-methylpyrrolidin-2-yl-methyl, glucosyl, rhamnosyl, ribosyl, deoxyribosyl, aminoglycosyl, 3-hydroxypropyl, 2-carboxyethyl, 2-dimethylaminoethylcarbonyl, dimethylaminomethylcarbonyl, 2-hydroxyethoxymethyl, (2-hydroxy-1-hydroxymethyl)-ethoxymethyl or (3-hydroxy-1-hydroxymethyl)-propoxymethyl radicals and RS
and/or Ra are hydrogen, chlorine, bromine or fluorine atoms or trifluoromethyl, methyl, ethyl, hydroxyl, benzyloxy, methoxy, amino, dimethylamino, 2-aminoethoxy, 3-aminopropoxy, 1-amino-2-propoxy, 2-dimethylaminoethoxy, 3-dimethylamino-1-propoxy, 5 3-dimethylamino-2-propoxy, 2-diethylaminoethoxy, 2-[N-benzyl-N-methylamino]-ethoxy, 3-[N-benzyl-N-methylamino]-propoxy, 3-dimethylamino-2-hydroxy-1-propoxy, 2-piperidinoethoxy, 3-piperidinopropoxy, 2-pyrrolidinoethoxy, 3-pyrrolidinopropoxy, 2-morpholinoethoxy, 3-morpholinopropoxy, 2-piperazinoethoxy, 3-piperazinopropoxy, pyrrolidin-2-ylmethoxy or N-methylpyrrolidin-2-ylmethoxy radicals or R4 and RS and/or R8 and R9 together represent a methylenedioxy radical.
The present invention is also concerned with the use of compounds of general formula I, including compounds in which R1 to R9 are hydrogen atoms or in which R4 or R4 and R9 are hydroxyl groups and the other symbols R1 to R9 are hydrogen atoms, for the preparation of pharmaceutical compositions for the prevention or treatment of diseases in which the inhibition of protein kinase C is of importance.
The present invention also provides pharmaceutical compositions which, in addition to conventional adjuvant and additive materials, contain at least one compound of general formula I, including compounds in which R1 to R9 are hydrogen atoms or in which R4 or R4 and R9 are hydroxyl groups and the other symbols R1 to R9 are hydrogen atoms.
The preparation of the compounds of general formula I
takes place analogously to the processes described in the literature (Tetrahedron, 44, 2887/1988; Tetrahedron Lett., 1985, 4015; European Patent Specification No. 0 269 025) or with the use of appropriate variations of these processes. The process according to the present invention is characterised in that either A) a dibromomaleinimide of the general formula II, Z
I
N
~- O
(II) Br Br in which Z is an appropriate protective group which can be split off, is reacted in known manner with an indole Grignard reagent of the general formula (A) R$
Rg' \ N
I
Mg Hal in which Ra and R9 have the above-given meanings except that they are not hydroxyl groups or acyloxy radicals, and the product obtained of the general formula III, Z
I
N
-O
R$
/ \Br (III) R9 \ N~
R' in which Rl is a hydrogen atom, is optionally alkylated in known manner on the indole nitrogen atom with an alkylation agent of the general formula R1-X, in which R1 has the same meaning as above with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions and X is a group which is easily removed, such as a chlorine or bromine atom, to give a compound of general formula III in which R1 is other than a hydrogen atom and subsequently the product of general formula III is reacted with an indole Grignard reagent of the general formula (B), i I
Mg Hal in which R4 and RS have the above-given meanings except that they are not hydroxyl groups or acyloxy radicals, and optionally subsequently alkylated with an alkylation agent of the general formula R2-X in which X has the above-given meaning and RZ has the above-given meaning with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions, to give a compound of the general formula IV, Z
I
O~N~-=p Rs ~ ~ ~ ~ ,R5 (IV) 3 0 Rs~ ~N~~Ra N
R' R2 whereafter the substituted imide group is converted into an unsubstituted imide group of general formula I; or B) a compound of the general formula V, Z
I
O
R:
(V) R' I
Y
in which Y and Z are appropriate protective groups which can be split off, is reacted with an indole Grignard reagent of the general formula (B), ( R4 \ N
I
Mg Hal in which R4 and RS have the above given meanings except that they are not hydroxyl groups or acyloxy radicals, and subsequently optionally alkylated with an alkylation agent of the general formula R2-X in which X has the above-given meaning and RZ has the above-given meaning with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions, to give a compound of the general formula VI
Z
I
R' R 5 (VI) R Ra whereafter the protected indole group is converted into a free indole group and the substituted imide group is converted into an unsubstituted imide group of general formula I
in which R1 is a hydrogen atom and Rz to R9 have the above-given meanings; or C) a dibromomaleinimide of the general formula II, Z
I
N
OO
(II) Br Br in which Z is an appropriate protective group which can be split off, is reacted with an excess of an indole Grignard reagent of the general formula (A), R$
R9 \ N
I
Mg Hal in which R8 and R9 have the above-given meanings with the exception of hydroxyl groups or acyloxy radicals, and the compound obtained of the general formula VII
Z
I
R' R $
(VII) I I
H H
is optionally alkylated on the indole nitrogen atom with an 10 alkylation agent of the general formula R1-X, in which R1 has the above-given meaning with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions and X is a group which can easily be removed, for example a chlorine or bromine atom, to give a compound of the general formula VIII
Z
I
~i R' R 8 (VIII) R' R 9 in which R1 is other than a hydrogen atom and Rz is a hydrogen atom and R8 and R9 have the above-given meanings with the exception of hydroxyl groups and acyloxy radicals, whereafter the substituted imide group is converted into an unsubstituted imide group of general formula I.
R1 Rz l0a Compounds of general formula VIII, in which R1 is other than a hydrogen atom and R2 is a hydrogen atom, can be reacted with an alkylation agent of the general formula R2-X, in which, with the exception of being a hydrogen atom and also does not contain a functional group which would disturb the following reactions, R2 has the above-given meaning and is different from R1 and X is a group which can easily be removed, for example, a chlorine or bromine atom, to give a compound of general formula VIII, in which R1 is different from RZ and both radicals are other than hydrogen.
After conversion of the substituted imide group in VII
or VIII into a free imide group, there are obtained compounds of general formula I in which R1 to R9 have the above-given meanings, R4 is the same as R9 and R5 is the same as R8.
Symmetrically substituted bis-indolylmaleinimides of general formula I, in which R1 and RZ are hydrogen atoms and R4 is the same as R9 and RS is the same as Ra and have the above-given meanings but are not hydroxyl groups or acyloxy radicals, can also be obtained by reacting dibromomaleinimide with an excess of indole Grignard reagent of general formula A.
The conversion of the substituted imides into the free imides described in processes A to C can be carried out analogously to the processes described in the literature. If, for example, Z is a methyl radical, then, by reaction with a solution of potassium hydroxide in water/methanol and subsequent acidification, there is first prepared the corresponding cyclic anhydride and this is converted by heating with ammonium acetate or ethanolic ammonia solution into the free imide (Tetrahedron, 44, 2887/1988). If, for example, Z is a benzyloxymethyl radical, then the conversion into the free imide is carried out lOb by hydrogenation in the presence of palladium/charcoal (Tetrahedron Lett., 26, 4015/1985).
As protective group Y in process B, there is especially preferred the tert.-butoxycarbonyl (BOC) radical, the p-toluenesulphonic acid (tosyl) radical and the trimethylsilylethoxymethyl (SEM) radical. The BOC and tosyl radicals are split off in the case of the conversion of the substituted imide into the free imide and the SEM radical can easily be split off with tetra-n-butylammonium fluoride (J. Org.
Chem., 49, 205/1984).
-m_ For carrying out the alkylations according to processes A to C
with compounds of the general formulae R1-X or R2-X, especially preferred bases include the hydrides, carbanates, amides, hydroxide, oxides and alkoxides of the alkali metals and alkaline earth metals and organo-lithium compounds. As solvents, it is especially preferred to use dipolar aprotic solvents, for example acetone, dimethyl sulphoxide, dimethylformamide or tetrahydrofuran. The glycosidation takes place with the use of appropriate t5-acylated glycosyl halides.
Compounds of general formula I, in which Rl and/or RZ are alkoxycarbonylalkyl radicals, can be prepared according to processes A to C, starting from N-benzyloxy-methyldibromomaleinimide with the use of appropriate alkoxycarbonylalkyl halides. In this case, the alkylation takes place after carrying out the reactions with the indole ~Grignard reagent. By reaction on the alkoxycarbonyl radicals with appropriate amines, there can be prepared herefrom the corresponding amides by known methods.
Compounds of the general formula I, in which R1 and/or RZ are haloalkyl radicals, are prepared from the corresponding hydroxyalkyl compounds by methods known far the conversion of an alcohol into a halide.
Compounds of the general formula T, in which R1 and/or R2 are amidinothioalkyl radicals, are prepared from the corresponding halides by reaction with thiourea.
Compounds of the general formula I, in which R1 and/or R2 are nitraguanidino alkyl radicals, are prepared from the corresponding aminoalkyl compounds by reaction with 1-nitroguanyl-~,4-dimethylpyrazole.
Compounds of the general formula I, in which R1 and/or R2 are isothiocyanotoalkyl radicals, are prepared from the corresponding aminoalkyl compounds by reaction with thiocarbonyldiimidazole.
Compounds of general formula I, in which R1 and/or Rz are both acyl radicals, are prepared from compounds of general formula I, in which R1 and/or RZ are hydrogen atoms, by a.cylation with the use of an appropriate aryl halide or anhydride in an appropriate solvent, for example pyridine.
Compounds of general formula I, in which R1 and/or RZ
are epoxyalkyl radicals, are prepared from compounds of general formula I, in which R1 and/or RZ are both hydrogen atoms and R4 to R9 have the above-given meanings but are not hydroxyl groups, by reaction with an appropriate haloepoxyalkane. If the reaction of haloepoxyalkanes takes place with compounds of general formula VI or VII and if Z is a methyl radical, then the epoxide ring is opened in the case of the conversion of the substituted imide into the free imide with the formation of vicinal diols, compounds being obtained of general formula I, in which R1 and/or R2 are dihydroxyalkyl radicals. The epoxide ring can also be opened with amines before splitting off the protective group Z. After conversion of the substituted imide group into the free imide group, there are obtained compounds of general formula I, in which R1 and/or R2 are aminohydroxyalkyl radicals.
Compounds of general formula I, in which one or up to four of the symbols R4 to R9 are hydroxyl groups, can be prepared in known manner by the ether splitting of compounds of general formula I, in which one or more of the symbols R4 to R9 are C1-C4-alkoxy radicals.
Compounds of general formula I, in which one or up to four of the symbols R4 to R9 are unsubstituted or substituted aminoalkoxy or acyloxy radicals, can be prepared in known manner by the aminoalkylation or acylation of compounds of general formula I, in which one or up to four of the symbols R4 to R9 are hydroxyl groups.
Compounds of general formula I may also be obtained by the processes described in EP-A-O 328 026.
Compounds of general formula I which have a chiral centre can be used in the form of stereoisomeric mixtures or in the form of enantiomers. The enantiomers can be obtained by the processes usually employed for the optical separation of stereoisomers.
Compounds of general formula I may be obtained as regioisomeric mixtures which may be separated into the single compounds by the usually known processes.
Thus another aspect of the present invention are the enantiomers of the stereoisomeric mixtures and the single compounds of the regioisomeric mixtures.
Basic compounds of general formula I which contain a basic centre on at least one of the substituents R1 to R9 are, for the purpose of purification and for galenical reasons, preferably converted into crystalline, pharmacologically acceptable salts. The salts are obtained in the usual way by neutralising the bases with appropriate inorganic or organic acids. As acids, there can be used, for example, hydrochloric acid, sulphuric acid, phosphoric acid, hydrobromic acid, acetic acid, tartaric acid, lactic acid, citric acid, malic acid, salicylic acid, ascorbic acid, malonic acid, fumaric acid, oxalic acid or succinic acid. As a rule, the acid-addition salts are obtained in known manner by mixing the free base or a solution thereof with an appropriate acid or a solution thereof in an organic solvent, for example a lower alcohol, such as 13a methanol, ethanol or propan-2-ol, or a lower ketone, such as acetone or butan-2-one, or an ether, such as diethyl ether, diisopropyl ether, tetrahydrofuran or dioxan.
The compounds according to the present invention are potent inhibitors of protein kinase C. Surprisingly they show a selective action, because much higher concentrations of the compounds of the present invention have to be used for inhibiting other kinases, for example the A-kinase, the G-kinase or the MLC-kinase. Especially this takes place for compounds of general formula I in which one indole group is unsubstituted on the indole nitrogen atom and the other indole group is appropriate substituted on the indole nitrogen atom and in the benzene moiety. Thus, for example the compound of example 1 shows, in the enzyme assay of protein kinase C, a 50%
inhibition at a concentration of 0,1~ ~amol/1, wheras the TC50-values of the inhibition of the A-kinase, G-kinase and MLC-kinase are 77 wmol/1, 15 umol/1 and ~.5 ~amol/1 respectively.
Protein kinase C plays an important key role for the intracellular signal transduction and is closely connected with the regulation of contractile, secretory and proliferative processes. On the basis of these properties, the compounds according to the present invention can be used for the treatment of heart and blood vessel diseases, such as thromboses, arterioskleroses and hypertension, of inflammatory processes, allergies, cancer and certain degenerative damages of the central nervous system, as well as of diseases of the immune system and viral diseases. Tn the particularly appropriate formulation, the compounds can be administered enterally or parenterally in doses of 1 to 500 mgjkg and preferably of 1 to 50 mg/kg. With respect to the good to excellent selectivity against PKC compared to other kinases the compounds of the present invention have much less side effects by the treatment of the above mentioned diseases.
The compounds of general formula T according to the present invention can be administered orally or parenterally in liquid or solid form. As injection solution, it is especially preferred to use water which contains the additives usual in the case of injection solutions, such as stabilising agents, solubilising agents and/or buffers. Such additives inClLide, for example, tartrate and citrate buffers, ethanol, complex formers (such as ethylenediamine-tetraacetic acid arid the non-toxic salts thereof), as well as high molecular weight polymers (such as liquid polyethylene oxide) for viscosity regulation. Solid carrier materials include, for example, starch, lactose, mannitol, methylcellulose, talc, highly dispersed silicic acids, high molecular weight fatty acids (such as stearic acid),'gelatine, agar-agar, calcium phosphate, magnesium stearate, animal and vegetable fats and solid high molecular weight polymers (such as polyethylene glycol). Compositions suitable for oral administration can, if desired, additionally contain flavouring and/or sweetening agents.
The following Examples are given for the purpose of illustrating the present invention:
Example 1 2-(1H-Indol-3-yl)-3-(1-meth.yl-1H-indol-3-yl)-maleinimide 0.3 g (0.87 mmol) 2-(iH-indol-3-yl)-3-(1-methyl-1H-indol-3-yl)-maleic acid anhydride and 15 g ammonium acetate are heated to 140°C. far 30 minutes. After cooling, the reaction mixture is stirred with a large amount of water, the red precipitate is filtered off with suction, well washed with water and dried in a vacuum at 0.1 Torr and 120°C. There is obtained 0.25 g (83%
of theory) of red product: m.p. 210°C. (decomp.); RF = 0.40 (tolu~ne/ethanol 10:2 v/v).
The 2-(1H-indol-3-yl)-3-(1-methyl-iH-indol-3-yl)-malefic acid anhydride used as starting material is prepared as follows: 0.5 g (1.4 morale) 2-(1H-indol-3-yl)-3-(1-methyl-iH-indol-3-yl)-N-methylmaleinimide and a solution of 10 g potassium hydroxide in 100 ml methanol/water (1:1 v/v) is heated under reflux for d hour. After cooling, the red reaction mixture is acidified with semiconcentrated hydrochloric acid and extracted with chloroform. After drying over anhydrous sodium sulphate, the extraction agent is removed by rotary evaporation and the residue is triturated with a little toluene. The red praduct is filtered off with suction and dried in a vacuum at 0.1 Torr and 70°C. Thmre is obtained 0.38 g (7~% of theory) of red crystals;
m.p. 234°C. (decomp.)p RF = 0.60 (toluene/ethanol 10:1 v/v).
The 2-(iH-indol-3-yl)-3-(1-methyl-1H-indol-3-°yl)-N-methylmaleinimide used as starting material is prepared as follows: A solution of 9.1 mmol ethyl magnesium bromide in 10 ml tetrahydrofuran is mixed with a solution of 1.1 g (g.i mmol) indole in 10 ml tetrahydrofuran. The reaction mixture is stirred for 1 hour at ambient temperature, mixed with a solution of 1.2 g (3.7 mmol) 2-broma-3-(1-methyl-iH-indol-3-yl)-Id-methylmaleinimide in 10 ml, tetrahydrofuran and heated under reflex for 4 hours. The reaction mixture is allowed to cool, decomposed with a saturated solution of ammonium chloride and extracted with ethyl acetate, After drying aver anhydrous sodium sulphate, the ethyl ester is removed by rotary evaporation and the residue is flash chromatographed on silica gel (Merck type 7734), using a mixture of toluene and ethanol (10+0.5 v/v) as elution agent. The unreacted starting material is first eluted and then the desired product. The product-containing fractions are combined, the elution agent is stripped off and the residue is triturated with a little toluene/petroleum ether. After suction filtration and drying in a vacuum at 0.1 Torr and 70°C, there is obtained 0.6 g of red crystals (45% of theory): m.p. 205°C; RF = 0.32 (toluene +
ethanol 10+2 v/v).
The 2-bromo-3-(1-methyl-1H-indol-3-yl)-N-methyl-maleinimide used as starting material is prepared as follows: 1.4 g (5 mmol) 2-bromo-3-(1H-indol-3-yl)-maleinimide is dissolved in 20 ml dimethylformamide and carefully mixed under an atmosphere of nitrogen with 0.3 sodium hydride (80% suspension in paraffin oil). The reaction mixture is further stirred for 1 hour at ambient temperature, mixed with a solution of 1.6 g (11.2 mmol) methyl iodide in 5 ml dimethylformamide and heated to 60°C for 6 hours. After cooling, the solvent is distilled off under water-pump vacuum and the residue is triturated with water. The orange-coloured precipitate is filtered off with suction and crystallised from a little methanol. There are obtained 1.3 g (81% of theory) of orange-coloured crystals; m.p. 167°C; RF =
0.48 (hexane/ethyl acetate 1:1 v/v).
The 2-bramo-3-(1H-indol-3-yl)-maleinimide used as starting material is prepared as follows: A solution of 49.3 mmol ethyl magnesium bromide in 30 ml tetrahydrof~ran is mixed with a solution o~ 5.8 g (49.5 mmol) indole in 50 ml toluene. The reaction mixture is stirred for 1 hour at arabient temperature, a solution of 2.5 g (9.8 mmol) dibromomaleinimide in 20 ml tetrahydrofuran/50 ml toluene is then slowly added dropwise thereto and heated under reflex for 30 hours. After cooling, the reaction mixture is decomposed with a saturated aqueous solution of ammonium chloride, the products are extracted with ethyl acetate and the organic phase is subsequently dried over anhydrous sodium sulphate. After evaporation, the red residue obtained is triturated with a little dichloromethane, filtered off with suction and dried in a vacuum at 0.1 Torr and 70°C.
There are obtained 2.2 g (75% of theory) of orange-coloured product; m.p. 196°c; RF = 0.35 (hexane/ethyl acetate i:1 vw).
Example 2 2-(1H-Indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide.
0.20 g (0,44 mmol) 2-(iH-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-malefic acid anhydride hydrochloride and 10 g ammonium acetate are heated to 140°G for 30 minutes. After cooling, the reaction mixture is mixed with water and extracted with ethyl acetate. The organic phase is well washed out with an aqueous solution of sodium bicarbonate and thereafter with water and dried over anhydrous sodium sulphate. The ethyl acetate is removed by rotary evaporation, the red residue obtained is stirred with a little water and the precipitated red product is filtered off with suction. After drying in a vacuum at 0.1 Torr and 14o°C, there is obtained 0.156 g (91% of theory) of red product; m.p. about 280°G
(decomp.): RF = 0.16 (chloroformjmethanol 10:2 v.v).
The 2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-malefic said anhydride used as starting material is prepared as follows: 0.5 g (0.95 mmol) 2-(1-tart.-butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl)-N-methyl-maleinimide and 50 ml of a 10% solution of potassium hydroxide in methanol/water (1:1 v/v) are heated under reflux for 30 minutes. After cooling, the reaction mixture is carefully acidified with concentrated hydrachloric acid and extracted with chloroform. The organic phase is washed out with water and evaporated to dryness. The red residue is triturated with a little methanol/toluene, filtered off with suction and dried at 80°C. There are obtained 0.34 g (79.5% of theory) of a dark red product; m.p. 232-234°C (decomp.).
The 2-(~.-tert.-butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-ylJ-N-methyl-maleinimide used as starting material is prepared as follows: A mixture of 0.9 g (2.03 mmol) 2-(I-tart.-butoxycarbonyl-1H-indol-3-yl)-3-(1H°-indol-3-yl)-N-methylmaleinimide (Tetrahedron, 44, 2887/1988), 0,3 g potassium carbonate and 0.3 g (2.4 moral) 3-dimethylaminopropyl chloride in ZO ml acetone is stirred for 12 hours at ambient temperature and for 8 hours under reflux.
After cooling, the reaction mixture is poured into water and extracted with ethyl acetate. The red extract is evaporated and the residue flash chromatographed on silica gel (Merck Type 7734) using, as elution agent, a mixture of toluene/ethanol (10+1.5 v/v). The desired product is obtained in the form of a red oil and used as such in the above reaction. Yield 0.8 g (T4% of theory); RF = o,zo (toluene/ethanal ~.:z v/v).
Example 3 2-(5-Hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide.
0.15 g (0.34 mmol) z-(5-benzyloxy-1H-indol-3-yl)~-3-(1H-indol-3-yl)-maleinimide and 4.0 g (34 mmol) pyridinium hydrochloride are heated under an atmosphere of nitrogen for 1 hour at 150°C.
After cooling, the reaction mixture is diluted with ice water and extracted with ethyl acetate. The organic phase is washed out with water and evaporated to dryness. The solid residue is triturated with a little water, filtered off with suction and dried in a vacuum at 0.1 Torr and 8o°C. There are obtained 85 mg (73% of theory) of dark red product; m.p. z00°205°C; RF
0.29 (toluene/ethanol 10:2 v/v).
z-(5-Benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide.
0.T g (1.6 moral) 2-(5-benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-malefic acid anhydride and 9.5 g ammonium acetate are heated to 140°C far 30 minutes. After cooling, the reaction mixture is _ lg _ stirred with water, the precipitate obtained is filtered off with suction, well washed out with water and dried in a vacuum at 0.1 Torr and 80°C. There is obtained 0.54 g (?8% of theory) of orange-coloured product: ~n.p. 308-312°C; RF = 0.29 (hexane/ethyl acetate 1:1 v/v).
The 2-(5-ben2yloxy-1H-indal-3-yl)-3-(1H-indol-3-yl)-malefic acid anhydride used as starting material is prepared as follows: A
solution of 1.0 g (1.83 mmol) 2-(5-benzyloxy-1H-indol-3-yl)-3-(1-tart.-butoxy-carbonyl-1H-indol-3-yl)-N-methylmaleinimide in 100 ml 10% potassium hydroxide solution (methanol/water 1:1 v/v) is heated under reflux for ~. hour. After cooling, the reaction mixture is carefully acidified with semi-concentrated hydrochloric acid, a red precipitate thereby being obtained.
The precipitate is filtered off with suction, well washed out with water and dried in the air. There is obtained 0,7 g (8?%
of theory) of orange-coloured product; m.p. 236°C~ RF = 0.43 (hexane/ethyl acetate 1:1 v/v).
The 2-(5-benzyloxy-1H-indol-3-yl)-3-(1-tart.-butoxycarbonyl-1H-indol-3-yl)-N-methylmaleinimide used as starting material is prepared as follows: A salution of 20 mmol ethyl magnesium bromide in 30 ml tetrahydrofuran is mixed with a solution of 4.46 g (20 mmol) 5-benzoxyindole in 20 ml tetrahydrofuran. The reaction mixture is maintained at 50°C for 1 hour and then, within the course of 1 hour, a solution of 3.0 g (7.4 mmol) 2-bromo-3-(1-tart.-butoxycarbonyl-1H-indol-3-yl]-N-methylmaleinimide (Tetrahedron, 44, 2887/1988) in 40 ml tetrahydrofuran added dropwise thereto. The reaction mixture is heated under reflux for 2 hours, allowed to cool and then decomposed with a saturated aqueous solution of ammonium chloride. The reaction product is extracted with ethyl acetate, the organic phase is dried over anhydrous sodium sulphate and evaporated to dryness. The residue is flash chromatographed on silica gel (Merck Type 7'734) using dichloromethane as elution agent. After elution of unreacted starting material, the desired product is obtained by evaporation of the appropriate fractions and stirring the red residue with a little toluene.
There are obtained 1.3 g (32% of theory) of red crystals; m.p.
123°C.
- 20 - ~~ ~ u~~~9:J
FxamQl a 5 2,3-Bis-(5-methoxy-1H-indol-3-yl)-maleinimide.
A solution of 22 mmol ethyl magnesium bromide in 30 ml tetrahydrofuran is mixed at ambient temperature with a solution of 2.8 g (19 mmol) 5-methoxyindole in 50 ml toluene and stirred for 1 hour at ambient temperature. Under an atmosphere of nitrogen, there is then added dropwise thereto a solution of 1.5 g (5.8 mmol) dibromomaleinimide in 20 ml tetrahydrofuran /
50 ml toluene and heated under reflux for 20 hours. After cooling, the reaction mixture is decomposed with a saturated aqueous solution of ammonium chloride, the products are extracted with ethyl acetate and the organic phase is dried over anhydrous sodium sulphate. After evaporat~.on, the red residue obtained is triturated with a little methanol and the precipitated red product is filtered off with suction and dried in a vacuum at 0.1 Torr and 100°C. There is obtained 0.9 g (36~
of theory) of red crystalsp m.p. 306°c (decamp.); RF = 0.30 (toluene/ethanol 10:2 v.v).
Hxample 6 2-(1H-Indol-3-y1)-3-(5,5-methylenedioxy-1H-indol-3-yl)-maleinimide.
0.8 g (2.1 mmol) 2-(1H-indol-3-yl)-0-(5,6-methylenedioxy-1H-indol-0-yl)-malefic acid anhydride, together with 20 g ammonium acetate, are heated far 1 hour to 140°C (melt). After cooling, the reaction mixture is mixed with water and the red-brown precipitate obtained is filtered off with suction. For purification, it is chromatagraphed on silica gel with dichloromethane/ethyl acetate (3:1 v/v) as elution agent. There is obtained o.4o g (45% of theory) 2-(~.H-indol-~-yl)-a-(5,6-methylenedioxy-1H-indol-0-yl)-maleinimide in the form of red crystals; m.p. 150°C (decamp.): ItF = 0.4 (methylene chloride/ethyl acetate 0:1 v/v).
The 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)-maleic acid anhydride used as starting material is prepared as followso 4.0 g (10.4 mmol) 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)-N-methylmaleinimide, together with a solution of 160 g potassium hydroxide in 1600 ml water, are heated under reflex for 30 minutes. The initially red suspension thereby passes aver into a brown solution. It is allowed to cool, acidified with concentrated hydrochloric acid and the red precipitate obtained is filtered off with suction.
There are obtained 3.40 g (88% of theory) 2-(1H-indol-3-yl)-3-(5,6-methylene-dioxy-1H-indol-3-yl)-malefic acid anhydride in the for~tt of bright red crystals: m.p. 200°C (decomp,) after recrystallisation from methanol; RF = 0.70 (dichloromethane/ethyl acetate 3:1 v/v).
The 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)-N-methylmaleinimide used as starting material is prepared as follows: 8.06 g (50 mmol) 5,6-methylenedioxy-indole are dissolved in 400 ml toluene and mixed at 60°C with 25 ml of a 2M solution of ethyl magnesium bromide in tetrahydrofuran (Aldrich). After 1 hour at 60°C, a solution of 8.1 g (20 mmol) 2-bromo-3-(Z-tert.-butyloxycarbonyl-1H-indol-3-yl)-N-methylmaleinimide in 100 ml toluene is added dropwise thereto, followed by heating under reflex for 3 hours. After cooling to ambient temperature, hydrolysis is carried out by the addition of 100 ml saturated aqueous a~nmoni.um chloride solution. The organic phase is separated off, the aqueous phase is sha:~en out with ethyl acetate, the residues are dissolved in ethyl acetate, the combined organic phases are dried and evaporated and thQ residue is chromatagraphed on 600 g silica gel with diohloromethane/ethyl acetate (3s1 v/v) as elution agent. There are obtained 3.75 g 5,6-methylenediaxyindole; m.p. 104-106°C, 0.55 g 2-bromo-3-(1H-indol-3-yl)-N-methylmaleinimide and 7.27 g (94% of theory) 2-(1H-indol-3-y1)-3-(5,6-methylenedioxy-1H-indal-3-yl)-N-methylmaleinimide fn the form of red crystals;
m.p. 140°C (decomp.); RF = 0.6 dichloromethane/ethyl acetate 3:1 v/v).
- 2 2 - ~'e 2-(1H-Indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide.
3.0 g (7.72 mmol) 2-(1H-indol-3-y1)-3-(5,6-dimethoxy-1H-indol-3-yl)-malefic acid anhydride, together with 75 g ammonium acetate, are heated to 140°C for 1 hour. After cooling, the reaction mixture is mixed with 1.5 1 of water and the dark red precipitate is filtered off with suction. There is obtained a crude yield of 2.61 g. For purification, 1.75 g thereof is chromatographed on silica gel with dichloromethane/ethyl acetate (8:1 v/v) as elution agent. There are obtained I.20 g 2-(1H-indol-3-y1)-3-(5,6-dimethoxy-1H-indal~~3-yl)-maleinimide x 0.5 ethyl acetate in the form of dark red crystals; m.p. 120°C
(decomp.}; RF = 0.32 (dichloromethane/ethyl acetate 3:1 v/v).
Yield 54% of theory.
The 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H°indol-3-yl)-malefic acid anhydride used as starting material is prepared as follows: 10 g (25 mmol} 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-N-~ethylmaleinimide are heated under reflex for 30 minutes in 4000 ml 10% aqueous potassium hydroxide solution.
The initially red suspension thereby passes over into a brown solution. After cooling, acidification is carried out with concentrated hydrochloric acid and the red precipitate obtained is filtered off with suction. The precipitate is heated in methanol and filtered. There are obtained 8.46 g 2-(1H-indol-3-yl}-3-(5,6-dimethoxy-iH-indol-3-yl)-malefic acid anhydride (87.6% of theory) in the form of dark red crystals; m.p. about 320°C (decomp.); RF = 0.50 (dichloromethane/ethyl acetate 3:1 v/v).
The 2- ( iH-indol-3-yl ) -3-- ( 5, 6-dimethoxy-1FI-indal-3-yl} -N-methylmaleinimide used as starting material is prepared as follows: 22.15 g (0.125 mol) 5,6- dimethoxyindole are dissolved in 1000 ml toluene and mixed at 40°C with 62.5 ml of a 21~
solution of ethyl magnesium bromide in tetrahydrofuran (Aldrich}. After 1 hour at 60°C, there is added dropwise a solutlan of 20.26 g (0.05 mol) 2-bromo-3-(1-tert.-butylaxycarbanyl-1H-indol-3-yl)-N-methylmaleinimide in 250 ml toluene, followed by heating under reflex for 3 hours. After cooling, hydrolysis is carried out by the addition of a saturated aqueous solution of ammonium chloride. The red precipitate formed is filtered off and chromatographed on silica gel with dichloromethane/ethyl acetate (10:1 v/v) as elution agent. There are obtained 6.51 g 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-N-methylmaleinimide (32% of theory) in the form of red crystals; m.p. 258°C~ RF = 0.44 (dichloromethane/ethyl acetate 3:1 v/v); and 7.17 g (about 35%
of theory) of red crystals of the same but slightly contaminated compound: m.p. 250°254°C.
ExamLle 8 2,3-Bis-(5,6-methylenedioxy-1H-indol-3-yl)-maleinimide.
6.44 g (40 mmol) 5,6-methylenedioxyindole are dissolved in 300 ml anhydrous toluene and mixed dropwise at 60°C with 20 ml of a 2ii solution of ethyl magnesium bromide in tetrahydrofuran (Aldrich). After completion of the addition, there is added dropwise thereto a solution of 1.7 g (6.67 mmol) dibromomaleinimide in 50 ml toluene, with the addition of the minimum amount of tetrahydrofuran required for solution, and then heated under reflex for 18 hours. After cooling, the reaction mixture is mixed with a saturated aqueous solution of ammonium chloride, the organic phase is separated off and the aqueous phase is extracted three times with toluene and once with ethyl acetate. The combined organic phases are dried, rotary evaporated and chromatographed in silica gel (elution agent: dichloromethane/ethyl acetate 30:1 v/v). There is obtained 1.27 g (56% of theory) 2-bromo-3-(5,6-methylenedioxy-1H-indol-3-yl)-maleinimide; m.p. about 185°C (decomp.); RF
0.50 (dichloromethane/ethyl acetate 3:1 v/v); and 0.63 g (22.5%
of theory) 2,3-bis-(5,6-methylenedi,oxy-1Fi-indol-3-yl)-maleinimide in the form of red crystals; m.p, about 270°C
(decomp.), after recrystallisation from propanolt RF = 0.36 (dichloromethane/ethyl aaeta~te 3:1 v/v).
2,3-Bis-(1H-indol-3-yl)-maleinimide was obtained in the manner described in the literature (Tetrahedron, 44, 2887/1988).
Example 10 2-(6-Hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide was obtained in the manner described in the li~tera~ture (Tetrahedron, 44, 2887/1988).
Tn an analogous manner to Examples 1 to 10 and to the other processes as disclosed there are obtained:
I
R' R 5 (VI) R Ra whereafter the protected indole group is converted into a free indole group and the substituted imide group is converted into an unsubstituted imide group of general formula I
in which R1 is a hydrogen atom and Rz to R9 have the above-given meanings; or C) a dibromomaleinimide of the general formula II, Z
I
N
OO
(II) Br Br in which Z is an appropriate protective group which can be split off, is reacted with an excess of an indole Grignard reagent of the general formula (A), R$
R9 \ N
I
Mg Hal in which R8 and R9 have the above-given meanings with the exception of hydroxyl groups or acyloxy radicals, and the compound obtained of the general formula VII
Z
I
R' R $
(VII) I I
H H
is optionally alkylated on the indole nitrogen atom with an 10 alkylation agent of the general formula R1-X, in which R1 has the above-given meaning with the exception of hydrogen and also does not contain a functional group which would disturb the following reactions and X is a group which can easily be removed, for example a chlorine or bromine atom, to give a compound of the general formula VIII
Z
I
~i R' R 8 (VIII) R' R 9 in which R1 is other than a hydrogen atom and Rz is a hydrogen atom and R8 and R9 have the above-given meanings with the exception of hydroxyl groups and acyloxy radicals, whereafter the substituted imide group is converted into an unsubstituted imide group of general formula I.
R1 Rz l0a Compounds of general formula VIII, in which R1 is other than a hydrogen atom and R2 is a hydrogen atom, can be reacted with an alkylation agent of the general formula R2-X, in which, with the exception of being a hydrogen atom and also does not contain a functional group which would disturb the following reactions, R2 has the above-given meaning and is different from R1 and X is a group which can easily be removed, for example, a chlorine or bromine atom, to give a compound of general formula VIII, in which R1 is different from RZ and both radicals are other than hydrogen.
After conversion of the substituted imide group in VII
or VIII into a free imide group, there are obtained compounds of general formula I in which R1 to R9 have the above-given meanings, R4 is the same as R9 and R5 is the same as R8.
Symmetrically substituted bis-indolylmaleinimides of general formula I, in which R1 and RZ are hydrogen atoms and R4 is the same as R9 and RS is the same as Ra and have the above-given meanings but are not hydroxyl groups or acyloxy radicals, can also be obtained by reacting dibromomaleinimide with an excess of indole Grignard reagent of general formula A.
The conversion of the substituted imides into the free imides described in processes A to C can be carried out analogously to the processes described in the literature. If, for example, Z is a methyl radical, then, by reaction with a solution of potassium hydroxide in water/methanol and subsequent acidification, there is first prepared the corresponding cyclic anhydride and this is converted by heating with ammonium acetate or ethanolic ammonia solution into the free imide (Tetrahedron, 44, 2887/1988). If, for example, Z is a benzyloxymethyl radical, then the conversion into the free imide is carried out lOb by hydrogenation in the presence of palladium/charcoal (Tetrahedron Lett., 26, 4015/1985).
As protective group Y in process B, there is especially preferred the tert.-butoxycarbonyl (BOC) radical, the p-toluenesulphonic acid (tosyl) radical and the trimethylsilylethoxymethyl (SEM) radical. The BOC and tosyl radicals are split off in the case of the conversion of the substituted imide into the free imide and the SEM radical can easily be split off with tetra-n-butylammonium fluoride (J. Org.
Chem., 49, 205/1984).
-m_ For carrying out the alkylations according to processes A to C
with compounds of the general formulae R1-X or R2-X, especially preferred bases include the hydrides, carbanates, amides, hydroxide, oxides and alkoxides of the alkali metals and alkaline earth metals and organo-lithium compounds. As solvents, it is especially preferred to use dipolar aprotic solvents, for example acetone, dimethyl sulphoxide, dimethylformamide or tetrahydrofuran. The glycosidation takes place with the use of appropriate t5-acylated glycosyl halides.
Compounds of general formula I, in which Rl and/or RZ are alkoxycarbonylalkyl radicals, can be prepared according to processes A to C, starting from N-benzyloxy-methyldibromomaleinimide with the use of appropriate alkoxycarbonylalkyl halides. In this case, the alkylation takes place after carrying out the reactions with the indole ~Grignard reagent. By reaction on the alkoxycarbonyl radicals with appropriate amines, there can be prepared herefrom the corresponding amides by known methods.
Compounds of the general formula I, in which R1 and/or RZ are haloalkyl radicals, are prepared from the corresponding hydroxyalkyl compounds by methods known far the conversion of an alcohol into a halide.
Compounds of the general formula T, in which R1 and/or R2 are amidinothioalkyl radicals, are prepared from the corresponding halides by reaction with thiourea.
Compounds of the general formula I, in which R1 and/or R2 are nitraguanidino alkyl radicals, are prepared from the corresponding aminoalkyl compounds by reaction with 1-nitroguanyl-~,4-dimethylpyrazole.
Compounds of the general formula I, in which R1 and/or R2 are isothiocyanotoalkyl radicals, are prepared from the corresponding aminoalkyl compounds by reaction with thiocarbonyldiimidazole.
Compounds of general formula I, in which R1 and/or Rz are both acyl radicals, are prepared from compounds of general formula I, in which R1 and/or RZ are hydrogen atoms, by a.cylation with the use of an appropriate aryl halide or anhydride in an appropriate solvent, for example pyridine.
Compounds of general formula I, in which R1 and/or RZ
are epoxyalkyl radicals, are prepared from compounds of general formula I, in which R1 and/or RZ are both hydrogen atoms and R4 to R9 have the above-given meanings but are not hydroxyl groups, by reaction with an appropriate haloepoxyalkane. If the reaction of haloepoxyalkanes takes place with compounds of general formula VI or VII and if Z is a methyl radical, then the epoxide ring is opened in the case of the conversion of the substituted imide into the free imide with the formation of vicinal diols, compounds being obtained of general formula I, in which R1 and/or R2 are dihydroxyalkyl radicals. The epoxide ring can also be opened with amines before splitting off the protective group Z. After conversion of the substituted imide group into the free imide group, there are obtained compounds of general formula I, in which R1 and/or R2 are aminohydroxyalkyl radicals.
Compounds of general formula I, in which one or up to four of the symbols R4 to R9 are hydroxyl groups, can be prepared in known manner by the ether splitting of compounds of general formula I, in which one or more of the symbols R4 to R9 are C1-C4-alkoxy radicals.
Compounds of general formula I, in which one or up to four of the symbols R4 to R9 are unsubstituted or substituted aminoalkoxy or acyloxy radicals, can be prepared in known manner by the aminoalkylation or acylation of compounds of general formula I, in which one or up to four of the symbols R4 to R9 are hydroxyl groups.
Compounds of general formula I may also be obtained by the processes described in EP-A-O 328 026.
Compounds of general formula I which have a chiral centre can be used in the form of stereoisomeric mixtures or in the form of enantiomers. The enantiomers can be obtained by the processes usually employed for the optical separation of stereoisomers.
Compounds of general formula I may be obtained as regioisomeric mixtures which may be separated into the single compounds by the usually known processes.
Thus another aspect of the present invention are the enantiomers of the stereoisomeric mixtures and the single compounds of the regioisomeric mixtures.
Basic compounds of general formula I which contain a basic centre on at least one of the substituents R1 to R9 are, for the purpose of purification and for galenical reasons, preferably converted into crystalline, pharmacologically acceptable salts. The salts are obtained in the usual way by neutralising the bases with appropriate inorganic or organic acids. As acids, there can be used, for example, hydrochloric acid, sulphuric acid, phosphoric acid, hydrobromic acid, acetic acid, tartaric acid, lactic acid, citric acid, malic acid, salicylic acid, ascorbic acid, malonic acid, fumaric acid, oxalic acid or succinic acid. As a rule, the acid-addition salts are obtained in known manner by mixing the free base or a solution thereof with an appropriate acid or a solution thereof in an organic solvent, for example a lower alcohol, such as 13a methanol, ethanol or propan-2-ol, or a lower ketone, such as acetone or butan-2-one, or an ether, such as diethyl ether, diisopropyl ether, tetrahydrofuran or dioxan.
The compounds according to the present invention are potent inhibitors of protein kinase C. Surprisingly they show a selective action, because much higher concentrations of the compounds of the present invention have to be used for inhibiting other kinases, for example the A-kinase, the G-kinase or the MLC-kinase. Especially this takes place for compounds of general formula I in which one indole group is unsubstituted on the indole nitrogen atom and the other indole group is appropriate substituted on the indole nitrogen atom and in the benzene moiety. Thus, for example the compound of example 1 shows, in the enzyme assay of protein kinase C, a 50%
inhibition at a concentration of 0,1~ ~amol/1, wheras the TC50-values of the inhibition of the A-kinase, G-kinase and MLC-kinase are 77 wmol/1, 15 umol/1 and ~.5 ~amol/1 respectively.
Protein kinase C plays an important key role for the intracellular signal transduction and is closely connected with the regulation of contractile, secretory and proliferative processes. On the basis of these properties, the compounds according to the present invention can be used for the treatment of heart and blood vessel diseases, such as thromboses, arterioskleroses and hypertension, of inflammatory processes, allergies, cancer and certain degenerative damages of the central nervous system, as well as of diseases of the immune system and viral diseases. Tn the particularly appropriate formulation, the compounds can be administered enterally or parenterally in doses of 1 to 500 mgjkg and preferably of 1 to 50 mg/kg. With respect to the good to excellent selectivity against PKC compared to other kinases the compounds of the present invention have much less side effects by the treatment of the above mentioned diseases.
The compounds of general formula T according to the present invention can be administered orally or parenterally in liquid or solid form. As injection solution, it is especially preferred to use water which contains the additives usual in the case of injection solutions, such as stabilising agents, solubilising agents and/or buffers. Such additives inClLide, for example, tartrate and citrate buffers, ethanol, complex formers (such as ethylenediamine-tetraacetic acid arid the non-toxic salts thereof), as well as high molecular weight polymers (such as liquid polyethylene oxide) for viscosity regulation. Solid carrier materials include, for example, starch, lactose, mannitol, methylcellulose, talc, highly dispersed silicic acids, high molecular weight fatty acids (such as stearic acid),'gelatine, agar-agar, calcium phosphate, magnesium stearate, animal and vegetable fats and solid high molecular weight polymers (such as polyethylene glycol). Compositions suitable for oral administration can, if desired, additionally contain flavouring and/or sweetening agents.
The following Examples are given for the purpose of illustrating the present invention:
Example 1 2-(1H-Indol-3-yl)-3-(1-meth.yl-1H-indol-3-yl)-maleinimide 0.3 g (0.87 mmol) 2-(iH-indol-3-yl)-3-(1-methyl-1H-indol-3-yl)-maleic acid anhydride and 15 g ammonium acetate are heated to 140°C. far 30 minutes. After cooling, the reaction mixture is stirred with a large amount of water, the red precipitate is filtered off with suction, well washed with water and dried in a vacuum at 0.1 Torr and 120°C. There is obtained 0.25 g (83%
of theory) of red product: m.p. 210°C. (decomp.); RF = 0.40 (tolu~ne/ethanol 10:2 v/v).
The 2-(1H-indol-3-yl)-3-(1-methyl-iH-indol-3-yl)-malefic acid anhydride used as starting material is prepared as follows: 0.5 g (1.4 morale) 2-(1H-indol-3-yl)-3-(1-methyl-iH-indol-3-yl)-N-methylmaleinimide and a solution of 10 g potassium hydroxide in 100 ml methanol/water (1:1 v/v) is heated under reflux for d hour. After cooling, the red reaction mixture is acidified with semiconcentrated hydrochloric acid and extracted with chloroform. After drying over anhydrous sodium sulphate, the extraction agent is removed by rotary evaporation and the residue is triturated with a little toluene. The red praduct is filtered off with suction and dried in a vacuum at 0.1 Torr and 70°C. Thmre is obtained 0.38 g (7~% of theory) of red crystals;
m.p. 234°C. (decomp.)p RF = 0.60 (toluene/ethanol 10:1 v/v).
The 2-(iH-indol-3-yl)-3-(1-methyl-1H-indol-3-°yl)-N-methylmaleinimide used as starting material is prepared as follows: A solution of 9.1 mmol ethyl magnesium bromide in 10 ml tetrahydrofuran is mixed with a solution of 1.1 g (g.i mmol) indole in 10 ml tetrahydrofuran. The reaction mixture is stirred for 1 hour at ambient temperature, mixed with a solution of 1.2 g (3.7 mmol) 2-broma-3-(1-methyl-iH-indol-3-yl)-Id-methylmaleinimide in 10 ml, tetrahydrofuran and heated under reflex for 4 hours. The reaction mixture is allowed to cool, decomposed with a saturated solution of ammonium chloride and extracted with ethyl acetate, After drying aver anhydrous sodium sulphate, the ethyl ester is removed by rotary evaporation and the residue is flash chromatographed on silica gel (Merck type 7734), using a mixture of toluene and ethanol (10+0.5 v/v) as elution agent. The unreacted starting material is first eluted and then the desired product. The product-containing fractions are combined, the elution agent is stripped off and the residue is triturated with a little toluene/petroleum ether. After suction filtration and drying in a vacuum at 0.1 Torr and 70°C, there is obtained 0.6 g of red crystals (45% of theory): m.p. 205°C; RF = 0.32 (toluene +
ethanol 10+2 v/v).
The 2-bromo-3-(1-methyl-1H-indol-3-yl)-N-methyl-maleinimide used as starting material is prepared as follows: 1.4 g (5 mmol) 2-bromo-3-(1H-indol-3-yl)-maleinimide is dissolved in 20 ml dimethylformamide and carefully mixed under an atmosphere of nitrogen with 0.3 sodium hydride (80% suspension in paraffin oil). The reaction mixture is further stirred for 1 hour at ambient temperature, mixed with a solution of 1.6 g (11.2 mmol) methyl iodide in 5 ml dimethylformamide and heated to 60°C for 6 hours. After cooling, the solvent is distilled off under water-pump vacuum and the residue is triturated with water. The orange-coloured precipitate is filtered off with suction and crystallised from a little methanol. There are obtained 1.3 g (81% of theory) of orange-coloured crystals; m.p. 167°C; RF =
0.48 (hexane/ethyl acetate 1:1 v/v).
The 2-bramo-3-(1H-indol-3-yl)-maleinimide used as starting material is prepared as follows: A solution of 49.3 mmol ethyl magnesium bromide in 30 ml tetrahydrof~ran is mixed with a solution o~ 5.8 g (49.5 mmol) indole in 50 ml toluene. The reaction mixture is stirred for 1 hour at arabient temperature, a solution of 2.5 g (9.8 mmol) dibromomaleinimide in 20 ml tetrahydrofuran/50 ml toluene is then slowly added dropwise thereto and heated under reflex for 30 hours. After cooling, the reaction mixture is decomposed with a saturated aqueous solution of ammonium chloride, the products are extracted with ethyl acetate and the organic phase is subsequently dried over anhydrous sodium sulphate. After evaporation, the red residue obtained is triturated with a little dichloromethane, filtered off with suction and dried in a vacuum at 0.1 Torr and 70°C.
There are obtained 2.2 g (75% of theory) of orange-coloured product; m.p. 196°c; RF = 0.35 (hexane/ethyl acetate i:1 vw).
Example 2 2-(1H-Indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide.
0.20 g (0,44 mmol) 2-(iH-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-malefic acid anhydride hydrochloride and 10 g ammonium acetate are heated to 140°G for 30 minutes. After cooling, the reaction mixture is mixed with water and extracted with ethyl acetate. The organic phase is well washed out with an aqueous solution of sodium bicarbonate and thereafter with water and dried over anhydrous sodium sulphate. The ethyl acetate is removed by rotary evaporation, the red residue obtained is stirred with a little water and the precipitated red product is filtered off with suction. After drying in a vacuum at 0.1 Torr and 14o°C, there is obtained 0.156 g (91% of theory) of red product; m.p. about 280°G
(decomp.): RF = 0.16 (chloroformjmethanol 10:2 v.v).
The 2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-malefic said anhydride used as starting material is prepared as follows: 0.5 g (0.95 mmol) 2-(1-tart.-butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl)-N-methyl-maleinimide and 50 ml of a 10% solution of potassium hydroxide in methanol/water (1:1 v/v) are heated under reflux for 30 minutes. After cooling, the reaction mixture is carefully acidified with concentrated hydrachloric acid and extracted with chloroform. The organic phase is washed out with water and evaporated to dryness. The red residue is triturated with a little methanol/toluene, filtered off with suction and dried at 80°C. There are obtained 0.34 g (79.5% of theory) of a dark red product; m.p. 232-234°C (decomp.).
The 2-(~.-tert.-butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-ylJ-N-methyl-maleinimide used as starting material is prepared as follows: A mixture of 0.9 g (2.03 mmol) 2-(I-tart.-butoxycarbonyl-1H-indol-3-yl)-3-(1H°-indol-3-yl)-N-methylmaleinimide (Tetrahedron, 44, 2887/1988), 0,3 g potassium carbonate and 0.3 g (2.4 moral) 3-dimethylaminopropyl chloride in ZO ml acetone is stirred for 12 hours at ambient temperature and for 8 hours under reflux.
After cooling, the reaction mixture is poured into water and extracted with ethyl acetate. The red extract is evaporated and the residue flash chromatographed on silica gel (Merck Type 7734) using, as elution agent, a mixture of toluene/ethanol (10+1.5 v/v). The desired product is obtained in the form of a red oil and used as such in the above reaction. Yield 0.8 g (T4% of theory); RF = o,zo (toluene/ethanal ~.:z v/v).
Example 3 2-(5-Hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide.
0.15 g (0.34 mmol) z-(5-benzyloxy-1H-indol-3-yl)~-3-(1H-indol-3-yl)-maleinimide and 4.0 g (34 mmol) pyridinium hydrochloride are heated under an atmosphere of nitrogen for 1 hour at 150°C.
After cooling, the reaction mixture is diluted with ice water and extracted with ethyl acetate. The organic phase is washed out with water and evaporated to dryness. The solid residue is triturated with a little water, filtered off with suction and dried in a vacuum at 0.1 Torr and 8o°C. There are obtained 85 mg (73% of theory) of dark red product; m.p. z00°205°C; RF
0.29 (toluene/ethanol 10:2 v/v).
z-(5-Benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide.
0.T g (1.6 moral) 2-(5-benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-malefic acid anhydride and 9.5 g ammonium acetate are heated to 140°C far 30 minutes. After cooling, the reaction mixture is _ lg _ stirred with water, the precipitate obtained is filtered off with suction, well washed out with water and dried in a vacuum at 0.1 Torr and 80°C. There is obtained 0.54 g (?8% of theory) of orange-coloured product: ~n.p. 308-312°C; RF = 0.29 (hexane/ethyl acetate 1:1 v/v).
The 2-(5-ben2yloxy-1H-indal-3-yl)-3-(1H-indol-3-yl)-malefic acid anhydride used as starting material is prepared as follows: A
solution of 1.0 g (1.83 mmol) 2-(5-benzyloxy-1H-indol-3-yl)-3-(1-tart.-butoxy-carbonyl-1H-indol-3-yl)-N-methylmaleinimide in 100 ml 10% potassium hydroxide solution (methanol/water 1:1 v/v) is heated under reflux for ~. hour. After cooling, the reaction mixture is carefully acidified with semi-concentrated hydrochloric acid, a red precipitate thereby being obtained.
The precipitate is filtered off with suction, well washed out with water and dried in the air. There is obtained 0,7 g (8?%
of theory) of orange-coloured product; m.p. 236°C~ RF = 0.43 (hexane/ethyl acetate 1:1 v/v).
The 2-(5-benzyloxy-1H-indol-3-yl)-3-(1-tart.-butoxycarbonyl-1H-indol-3-yl)-N-methylmaleinimide used as starting material is prepared as follows: A salution of 20 mmol ethyl magnesium bromide in 30 ml tetrahydrofuran is mixed with a solution of 4.46 g (20 mmol) 5-benzoxyindole in 20 ml tetrahydrofuran. The reaction mixture is maintained at 50°C for 1 hour and then, within the course of 1 hour, a solution of 3.0 g (7.4 mmol) 2-bromo-3-(1-tart.-butoxycarbonyl-1H-indol-3-yl]-N-methylmaleinimide (Tetrahedron, 44, 2887/1988) in 40 ml tetrahydrofuran added dropwise thereto. The reaction mixture is heated under reflux for 2 hours, allowed to cool and then decomposed with a saturated aqueous solution of ammonium chloride. The reaction product is extracted with ethyl acetate, the organic phase is dried over anhydrous sodium sulphate and evaporated to dryness. The residue is flash chromatographed on silica gel (Merck Type 7'734) using dichloromethane as elution agent. After elution of unreacted starting material, the desired product is obtained by evaporation of the appropriate fractions and stirring the red residue with a little toluene.
There are obtained 1.3 g (32% of theory) of red crystals; m.p.
123°C.
- 20 - ~~ ~ u~~~9:J
FxamQl a 5 2,3-Bis-(5-methoxy-1H-indol-3-yl)-maleinimide.
A solution of 22 mmol ethyl magnesium bromide in 30 ml tetrahydrofuran is mixed at ambient temperature with a solution of 2.8 g (19 mmol) 5-methoxyindole in 50 ml toluene and stirred for 1 hour at ambient temperature. Under an atmosphere of nitrogen, there is then added dropwise thereto a solution of 1.5 g (5.8 mmol) dibromomaleinimide in 20 ml tetrahydrofuran /
50 ml toluene and heated under reflux for 20 hours. After cooling, the reaction mixture is decomposed with a saturated aqueous solution of ammonium chloride, the products are extracted with ethyl acetate and the organic phase is dried over anhydrous sodium sulphate. After evaporat~.on, the red residue obtained is triturated with a little methanol and the precipitated red product is filtered off with suction and dried in a vacuum at 0.1 Torr and 100°C. There is obtained 0.9 g (36~
of theory) of red crystalsp m.p. 306°c (decamp.); RF = 0.30 (toluene/ethanol 10:2 v.v).
Hxample 6 2-(1H-Indol-3-y1)-3-(5,5-methylenedioxy-1H-indol-3-yl)-maleinimide.
0.8 g (2.1 mmol) 2-(1H-indol-3-yl)-0-(5,6-methylenedioxy-1H-indol-0-yl)-malefic acid anhydride, together with 20 g ammonium acetate, are heated far 1 hour to 140°C (melt). After cooling, the reaction mixture is mixed with water and the red-brown precipitate obtained is filtered off with suction. For purification, it is chromatagraphed on silica gel with dichloromethane/ethyl acetate (3:1 v/v) as elution agent. There is obtained o.4o g (45% of theory) 2-(~.H-indol-~-yl)-a-(5,6-methylenedioxy-1H-indol-0-yl)-maleinimide in the form of red crystals; m.p. 150°C (decamp.): ItF = 0.4 (methylene chloride/ethyl acetate 0:1 v/v).
The 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)-maleic acid anhydride used as starting material is prepared as followso 4.0 g (10.4 mmol) 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)-N-methylmaleinimide, together with a solution of 160 g potassium hydroxide in 1600 ml water, are heated under reflex for 30 minutes. The initially red suspension thereby passes aver into a brown solution. It is allowed to cool, acidified with concentrated hydrochloric acid and the red precipitate obtained is filtered off with suction.
There are obtained 3.40 g (88% of theory) 2-(1H-indol-3-yl)-3-(5,6-methylene-dioxy-1H-indol-3-yl)-malefic acid anhydride in the for~tt of bright red crystals: m.p. 200°C (decomp,) after recrystallisation from methanol; RF = 0.70 (dichloromethane/ethyl acetate 3:1 v/v).
The 2-(1H-indol-3-yl)-3-(5,6-methylenedioxy-1H-indol-3-yl)-N-methylmaleinimide used as starting material is prepared as follows: 8.06 g (50 mmol) 5,6-methylenedioxy-indole are dissolved in 400 ml toluene and mixed at 60°C with 25 ml of a 2M solution of ethyl magnesium bromide in tetrahydrofuran (Aldrich). After 1 hour at 60°C, a solution of 8.1 g (20 mmol) 2-bromo-3-(Z-tert.-butyloxycarbonyl-1H-indol-3-yl)-N-methylmaleinimide in 100 ml toluene is added dropwise thereto, followed by heating under reflex for 3 hours. After cooling to ambient temperature, hydrolysis is carried out by the addition of 100 ml saturated aqueous a~nmoni.um chloride solution. The organic phase is separated off, the aqueous phase is sha:~en out with ethyl acetate, the residues are dissolved in ethyl acetate, the combined organic phases are dried and evaporated and thQ residue is chromatagraphed on 600 g silica gel with diohloromethane/ethyl acetate (3s1 v/v) as elution agent. There are obtained 3.75 g 5,6-methylenediaxyindole; m.p. 104-106°C, 0.55 g 2-bromo-3-(1H-indol-3-yl)-N-methylmaleinimide and 7.27 g (94% of theory) 2-(1H-indol-3-y1)-3-(5,6-methylenedioxy-1H-indal-3-yl)-N-methylmaleinimide fn the form of red crystals;
m.p. 140°C (decomp.); RF = 0.6 dichloromethane/ethyl acetate 3:1 v/v).
- 2 2 - ~'e 2-(1H-Indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide.
3.0 g (7.72 mmol) 2-(1H-indol-3-y1)-3-(5,6-dimethoxy-1H-indol-3-yl)-malefic acid anhydride, together with 75 g ammonium acetate, are heated to 140°C for 1 hour. After cooling, the reaction mixture is mixed with 1.5 1 of water and the dark red precipitate is filtered off with suction. There is obtained a crude yield of 2.61 g. For purification, 1.75 g thereof is chromatographed on silica gel with dichloromethane/ethyl acetate (8:1 v/v) as elution agent. There are obtained I.20 g 2-(1H-indol-3-y1)-3-(5,6-dimethoxy-1H-indal~~3-yl)-maleinimide x 0.5 ethyl acetate in the form of dark red crystals; m.p. 120°C
(decomp.}; RF = 0.32 (dichloromethane/ethyl acetate 3:1 v/v).
Yield 54% of theory.
The 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H°indol-3-yl)-malefic acid anhydride used as starting material is prepared as follows: 10 g (25 mmol} 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-N-~ethylmaleinimide are heated under reflex for 30 minutes in 4000 ml 10% aqueous potassium hydroxide solution.
The initially red suspension thereby passes over into a brown solution. After cooling, acidification is carried out with concentrated hydrochloric acid and the red precipitate obtained is filtered off with suction. The precipitate is heated in methanol and filtered. There are obtained 8.46 g 2-(1H-indol-3-yl}-3-(5,6-dimethoxy-iH-indol-3-yl)-malefic acid anhydride (87.6% of theory) in the form of dark red crystals; m.p. about 320°C (decomp.); RF = 0.50 (dichloromethane/ethyl acetate 3:1 v/v).
The 2- ( iH-indol-3-yl ) -3-- ( 5, 6-dimethoxy-1FI-indal-3-yl} -N-methylmaleinimide used as starting material is prepared as follows: 22.15 g (0.125 mol) 5,6- dimethoxyindole are dissolved in 1000 ml toluene and mixed at 40°C with 62.5 ml of a 21~
solution of ethyl magnesium bromide in tetrahydrofuran (Aldrich}. After 1 hour at 60°C, there is added dropwise a solutlan of 20.26 g (0.05 mol) 2-bromo-3-(1-tert.-butylaxycarbanyl-1H-indol-3-yl)-N-methylmaleinimide in 250 ml toluene, followed by heating under reflex for 3 hours. After cooling, hydrolysis is carried out by the addition of a saturated aqueous solution of ammonium chloride. The red precipitate formed is filtered off and chromatographed on silica gel with dichloromethane/ethyl acetate (10:1 v/v) as elution agent. There are obtained 6.51 g 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)-N-methylmaleinimide (32% of theory) in the form of red crystals; m.p. 258°C~ RF = 0.44 (dichloromethane/ethyl acetate 3:1 v/v); and 7.17 g (about 35%
of theory) of red crystals of the same but slightly contaminated compound: m.p. 250°254°C.
ExamLle 8 2,3-Bis-(5,6-methylenedioxy-1H-indol-3-yl)-maleinimide.
6.44 g (40 mmol) 5,6-methylenedioxyindole are dissolved in 300 ml anhydrous toluene and mixed dropwise at 60°C with 20 ml of a 2ii solution of ethyl magnesium bromide in tetrahydrofuran (Aldrich). After completion of the addition, there is added dropwise thereto a solution of 1.7 g (6.67 mmol) dibromomaleinimide in 50 ml toluene, with the addition of the minimum amount of tetrahydrofuran required for solution, and then heated under reflex for 18 hours. After cooling, the reaction mixture is mixed with a saturated aqueous solution of ammonium chloride, the organic phase is separated off and the aqueous phase is extracted three times with toluene and once with ethyl acetate. The combined organic phases are dried, rotary evaporated and chromatographed in silica gel (elution agent: dichloromethane/ethyl acetate 30:1 v/v). There is obtained 1.27 g (56% of theory) 2-bromo-3-(5,6-methylenedioxy-1H-indol-3-yl)-maleinimide; m.p. about 185°C (decomp.); RF
0.50 (dichloromethane/ethyl acetate 3:1 v/v); and 0.63 g (22.5%
of theory) 2,3-bis-(5,6-methylenedi,oxy-1Fi-indol-3-yl)-maleinimide in the form of red crystals; m.p, about 270°C
(decomp.), after recrystallisation from propanolt RF = 0.36 (dichloromethane/ethyl aaeta~te 3:1 v/v).
2,3-Bis-(1H-indol-3-yl)-maleinimide was obtained in the manner described in the literature (Tetrahedron, 44, 2887/1988).
Example 10 2-(6-Hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide was obtained in the manner described in the li~tera~ture (Tetrahedron, 44, 2887/1988).
Tn an analogous manner to Examples 1 to 10 and to the other processes as disclosed there are obtained:
11.) 2-(5-benzyloxy-1H-indol-3-yl)-3-[1-(3~-dimethylaminopropyl)-1H-indol-3-yl]maleinimide, 188-189°C;
12.) 2-[5-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleinimide, 240-241°C:
13°) 2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide, 250-251°C;
14.) (~)-2-(1H-indol-3-yl)-3-[1-(3-dimethylamino-2-methoxypropyl)-1H-indal-3-yl]maleinimide, 218°C, decomp.;
15.) 2-(iH-indol-3-yl)-3-[5-(3-dimethylaminopropyloxy)-iH-indol-3-yl]maleinimide, 235°C;
16.) 2,3-bis-(5-fluora-1H-indol-3-yl)maleinimide, 320°C, decomp.;
17.) 2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-dimethylaminopropyl)-iH-indol-3-yl]maleinimide, 283-285°C;
18°) 2,3-bis-(5-benzyloxy-iH-indol-3-yl)maleinimide, 1.30°C, 'LerB ° ;
19.) 2-(5-benzyloxy-iH-indol-3-yl)-3-[5-benzylaxy-1-(3-dimethylaminopropyl-iH-indal-3-yl]maleinimide, 277°C, Zers.;
20°) 2-(s-benzyloxy-1-methyl-iH-indol-3-yl)-3-(1-methyl-iH-indol-3-yl)maleinimide;
- 25 _ 21.) 2-[5-benzylo~y-1-(3-dimethylaminopropyl)°1H-indol-3-yl]-3-(1-methyl-1H-indol-3-yl)maleinimide, 181-182°Cf 22.) 2,3-bis-(5-chloro-1H-indol-3-yl)maleinimide, 279-281°C, deGOmp.i 23.) 2-(5-chloro-iH-indol-3-yl)-3-[5-chloro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide, 255-257°C, decomp.;
- 25 _ 21.) 2-[5-benzylo~y-1-(3-dimethylaminopropyl)°1H-indol-3-yl]-3-(1-methyl-1H-indol-3-yl)maleinimide, 181-182°Cf 22.) 2,3-bis-(5-chloro-1H-indol-3-yl)maleinimide, 279-281°C, deGOmp.i 23.) 2-(5-chloro-iH-indol-3-yl)-3-[5-chloro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide, 255-257°C, decomp.;
24.) 2,3-bis-(5-methyl-1H-indol-3-yl)maleinimide, 180°C, decomp.;
25.) 2-(5-methyl°1H-indol-3-yl)-3-[5-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide, 215°C;
26°) 2,3-bis-(5-brom-1H-indol-3-yl)maleinimide, 351°C;
27.) 2-(5-bromo-1H-indol-3-yl)-3-[5°bromo-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide, 257-258°C;
28.) 2-(1H-indol°3-yl)-3-[1-(3-dimethylaminoethyl)-1H°indol-3-yl]-maleinimide, pale red crystals, 246-248°C, decomp., prepared by process C:
29.) 2-(~.H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-iH-indol-3-yl]-maleinimide, pale orange crystals, 204°C, prepared by process C;
30.) 2-(1H-indol-3-yl)-3~-[1-(3-(4-morpholina)propyl)-1H-indol-3-yl]-maleinimide, pale orange crystals, 285-287°C, decomp., prepared by process C;
31.) 2-[1-(3-diethylaminopropyl)-1FI-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, pale orange crystals, 241-242°C, decomp., prepared by process C;
32.) (~)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide, dark red crystals, 158°C, prepared by process C by use of 1,1-diethyl-3-hydroxyazetidiniumchloride as alkylating agent;
33.) 2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indo~.-3-yl]-maleinimide, pale orange crystals, 224-225°C, prepared by process C by use of the SEM protecting group;
34.) 2-(2H-indol-3-yl)-3-[5-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide, pale red crystals, 234-236°C, prepared by process B by use of the SEM protecting group;
35.) (~)-2-[1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, dark red crystals, 135°C, prepared by process B by use of the BOC protecting group and epibromohydrin as alkylating agent;
36.) 2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-1H-indol-3-y1]-maleinimide arid 37.) 2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(4-morpholino)-propyl)-1H-indol-3-yl]-maleinimide, as regioisomeric mixture 1:1, orange crystals, 132-135°C, prepared by process B by use of the BOC protecting group;
3S.) (~)-2-[1.-(3-Ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, dark red crystals, 130-134°C
prepared by process B by use of the BoC protecting group and epibromohydrin as alkylating agent;
39.) (~)-2-[1-(2-hydroxy-3-(~.-piperidino)-propyl)-1~i-indol-3-yl]-3-(1H-indol-3-yl)-malainimide, dark red crystals, 142°C, decomp., prepared by process B by use of the Bnc protecting group and epibromohydrin as alkylatirig agent;
4a.) (t)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide and 41.) (~)-2-[1-(3-diethylamirio-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide, as regioisomeric mixture 4:1, dark red crystals, above 150°C decomp., prepared by process B by use of the BOC protecting group and 1,1-diethyl-3-hydroxyazetidinium-chloride as alkylating agent;
42.) 2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide, 257°258°C, and with 43.) 2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide, as regioisomeric mixture 1:1, orange crystals, 150°C, prepared by pz~ocess B by use of the BOC protecting group:
44.) 2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-maleinimide, pale red crystals, 165-166°C, prepared by process A;
45.) 2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide and 46.) 2-[1-(3-diethylaminopropyl)-1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide, as regioisomeric mixture 3:2, pale red crystals, 206-208°C, decomp, prepared by process B by use of the BOC protecting group;
47.) 2-[1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide and 48.) 2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, as regioisomeric mixture 3:1, pale red crystals, 285-190'C, prepared by process B.
49.) 2-[~.-(3-diethylaminapropyl)-5-methoxy-1H-indol-3-yl]-3-(6-methoxy-1FI-indol-3-yl)-maleinimide and 50.) 2-[1-(3-diethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide, as regioisomeric mixture 5:1, red crystals, 176-182'C, prepared by process B.
-51.) 2-[5-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide and 52.) 2-(5-floor-iH-indol-3-yl)-3-[1-{3-dimethylaminoplopyl)-iH-indol-3-yl]-maleinimide, as regioisomeric mixture 3:1, 230-235°C.
Tn analogous manner the following compounds are prepared according to their substituents by one of the disclosed processes:
2-[1-(3-(amidinothio)propyl)-1H-indol-3-yl]~-3-{iH-indol-3-yl)-maleinimide;
2-[1-{2-aminoethyl)-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-[1-{3-aminopropyl)-iH-indol~3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
{-~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminoprapyl)-1H-indol-3-yl]-3-(iFI-indol-3-yl)-maleinimide;
(~)-2-[1-[2-hydroxy-3-(4-morpholino)prapyl]-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)_2-[1-.[2-hydroxy-3-(~-morpholino)propyl]-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
_ 29 -(-)-2-[1-[2-hydroxy-3-(4-morpholino)propyl]-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
2-(1H-indol-3-y1)-3-[1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(2H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylami.nopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-[3-(2-nitroguanidino)propyl]-1H-indol-3-yl]-maleinimide;
2-(4-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(6-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(7-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(4-amino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(C-amino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(7-amino-1H-indol-3-yl}-3-(1H-indol-3-yl)-maleinimide; .
2-(4-benzyloxy-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(5-benzyloxy-1H-indol-3-yl}-3-(iH-indol-3-yl)-maleinimide;
2-(s-benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(7-benzyloxy-1H-indol-3-yl}-3-(1H-indol-3-yl)-maleinimide;
2-(4-bromo-1H-indol-3-yl)-3-(iH-indol-3-yl}~-maleinimide;
2-(5-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2_(6_bromo-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(7-bromo-iH-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(4-chloro-iH-indol-3-yl)-3-(iH-indol-3-yl}-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(6-chloro-1H-indal-3-yl}-3-(iH-indol-3-yl)-maleinimide;
2-(7-chloro-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(4-fluoro-1H-indol-3-yl}-3-(1H-indol-3-yl)-maleinimide;
2-(5-fluoro-iH-indol-3-yl}-3-(iH-indol-3-yl)-maleinimide;
2-(6-fluoro-iH-indol-3-yl)-3-(1H-indol-3-yl}-malainimide;
2-(7-fluoro-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(4-hydroxy-1H-indol-3-yl)-3-(iH-indal-3-yl)-maleinimide;
2-(5-hydroxy-1H-indol-3-yl}-3-(iH-indol-3-yl}-maleinimide;
2-(6-hydroxy-1H-indol-3-yl}~-3-(1H-indol-3-yl)-maleinimide;
2-(7-hydroxy-1H-indoi-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(4-trifluoromethyl-1H-indol-3-yl)-~-(1H-indol-3-yl)-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
a-(6-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-~-yl)-malelnlmlde;
2-(7-trifluoromethyl-1H-indol-3~y1)-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(4-methaxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(7-methoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indoi-3-yl)-s-(~,5-methylendioxy-1H-indol-3-y1)-maleinimide;
2-(1.H-indol-3-yl)-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6,7-methylendioxy-1H~indol-3-yl)-maleinimide;
2-(1H-~.ndol-3-yl)-3-(4-methyl-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6-methyl-1H-indol-3-yl)-maleinimide;
2-(1~I-indol-3-yl)-3-(7-methyl-1H-indol-3-yl)-maleinimide;
2-(iH-indol-3-yl)-3-(4-nitro-1H-indol-3-yl)-maleinimide;
~3~.-2-(1H-indol-3-yl)-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6-vitro-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(7-vitro-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(4-methylthio-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methylthio-1H-indol-3-yl)-maleinimide:
2-(1H-indol-3-yl)-3-(6-methylthio-1H-indol-~3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(7-methylthio-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(~,5-dimethoxy-1H-indol-~--yl)-maleinimide;
2-(1H~-indol-3-yl)-3-(5,~-dimethoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6,7-dimethoxy-1H-indol-3-yl)-maleinimide;
2-(4-acetylamino-1.-(3-(amidinothio)propyl)-1H-indol-:~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
~°[6-aGetylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(1H--indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-amino-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-amino--1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-amino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-7-amino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-5-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-benzyloxy-1H-indol-3-y1,]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-7-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
2-[1-(3-(amidinothia)propyl)-4-bromo-1H-indol-3-yl]-3-(1H°-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-5-bromo-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-6-bromo-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-7-bromo-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-6-chloro-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-7-chloro-1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-{3-(amidinothio)propyl)-4-fluaro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-{3-(amidinothio)propyl)-4-hydroxy-iH-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-hydroxy-1H-indol-3-ylJ-3-{1H-indol-3-yI)-maleinimide;
2-[1-{3-(amidinothio)propyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-trifluoromethyl-2H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-trifl~oromethyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidino~hio)propyl)-?-trifluoramethyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-methoxy-~iH~indol~3-ylJ-3-(iH-indol-3-yl)-maleinimide;
- 35 - ~~~~t3 2-[1-(3-(amidinothio)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-s-methoxy-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1-(3-(amidinothio)propyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4,5-methylendioxy-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)~5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6,7-methylendioxy-1H-indol-3-yT]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-methyl-1H-indol-3-yl]-3-(:LH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-methyl-7.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1-(3-(amidinothio)propyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)prapyl)-7-methyl-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
z-~~.--(s-(amiainothio)propyl)-a-vitro-~.H-indol-s-yl]-s-(iH-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol -3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-vitro-2H-indol-3-yl]-3-(1H-indnl-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-7-vitro-iH-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[1-(3-(amidinothio}propyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio}propyl)-5-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio}propyl}-6-methylthio-1;H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(3-(amidinothio}propyl}-4,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio}propyl}-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(3-(amidinothio)propyl}-6,7-dimethoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-acetylamino-1-(2-aminoethyl)-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
2-[5-acetylamino-Z'(2-aminoethyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-aaetylamino-1-(2-aminoethyl)-iH-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[7-acetylamino-1-(2-aminaethyl}-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4- amino-1-(2-aminoethyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
_3~-2-[5-amino-~,-(2-aminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(2-aminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(2-aminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[~.-(2-aminoethyl)-4-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(~-aminoethyl)-5-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(2-aminoethyl)-6-benzyloxy-aH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
~-[1-(2-aminoethyl)-'7-benzyloxy-1H-indol-3-y1]-3-(~.H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-~-bromo-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(2-aminoethyl)-5-bromo-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-bromo-1H-indol~3-yl]-3-(1H-indol-3-yl)-maleinimide;
x-[1-(2-aminoethyl)-7-bromo-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimid~;
2-[1-(2~aminoethyl)-4-chloro-1F~-indol-3-yl]-~-(1H-indol-3-yl)~
maleinimide;
2-[1-(2-aminoethyl)-5-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-~8-z-[1-(z-aminoethyl)-6-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-7-chloro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-4-fluoro-1H-indol-~-yl]-~-(iH-indol-3-yI}-maleinimide;
2-[1-(z°aminoethyl)-5-fluoro-1H-indol-3-yl]~-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-~-yl}-maleinimide;
2-[1-(2-aminoethyl)-7-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[1-(z-aminoethyl)-4-hydroxy-iH-indol-3-yl]-3-(1H-indol--3-yl}-maleinimide;
2-[1-(z-aminoethyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-6-hydroxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-7-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-trifluoromethyl-1~I-indol-3-yl]-a-(iH-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-trifluoromethyl-iH-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
°
2-[1-(2-aminoethyl)-7-tri~luoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-~-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol~3-yl)--maleinimidet 2-[1-(2-aminoethyl)-6-methoxy-1H-indol-3-yl;j-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl.)-4,5-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[1-(2-aminoethyl)-4-methyl~iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1~(2~aminoethyl)-6-methyl-1H-indol~3-yl]~3-(iH-indol-3-yl)~
maleinimide;
2-[1~(2~aminoethyl)-7-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4-vitro-1H-indol~3-yl]~3~(1H~indol-3~yl)-maleinimide:
-2-[1-(2-aminoethyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(~-aminoethyl)-7-vitro-iH-indol-3-yl]--3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~.-(2-aminoethyl)-5-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[1-(2-aminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[1-(~-aminoethyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~1-acetylamino-1-(3-aminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5wacetylamino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-aminopropyl)~1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
--~. ~~~.~~r~
2-[?-ace~ylamino-1-(3-aminopropyl)-iH-indol-3-yl]-3-(iH-indal-3-ylj-maleinimide;
2-[4-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)°
maleinimide;
2-[6-amino-1-(3-aminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
2-[1-(3-aminopropyl)-4-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-benzyloxy-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-6-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yIj-maleinimide:
2-[1-(~-aminopropyl)-7-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(3-aminopropyl)-4-bromo-1H-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-bromo-iH-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[1-(a-aminopropyl)-6-bromo-1H-indal-3-yl]-3~(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-7-bromo-iH-indol-3-yl]-3-(1H-indal-~-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-chloro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-chloro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-chloro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-7-chloro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-fluoro-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-fluoro-iH-indol-3-yl]-3-(1H-indol-~3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-fluoro-1H-indol-3-yl]-3-(iH-indol-~-y1)-maleinimide;
2-[1-(3-aminopropyl)-7-fluoro-1H-indal-3-yl]°~-(1H-indol-~-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-hydroxy-1H-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(~-aminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-hydroxy-iH-indol-3-yl]-3-(1H-indo:!-3-yl)-maleinimide;
Z-[1-(3-aminopropyl)-7-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-trifluoromethyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-rnaleinimide:
-~3-2-(1-(3-aminopropyl)-5-tri~luoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~.-(3-aminopropyl)-7-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yI)-maleinimide;
2-[~.~(3-aminopropyl}-5-methoxy-1H-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
2-[1-(3-aminopropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-7-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(1-(3-aminopropyl}-~,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[1-(3-aminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl}-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
~-[1-(3-aminoprapyl)-4-methyl-iH-indol-3~yl]-3-(iH-indol-3-yl)-maleinimide 2-[1-(3-aminopropyl)-5-methyl-iH-indol-3-yl]-3-(iH-indol--3-yl)-maleinimide;
2-(1-(3-aminoprapyl)-6-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-~4-2-[1~-(3-aminopropyl)-7-methyl-1H-indol-3-ylJ-3-(1H-indol-°3-yl)-maieinimide;
2-[1-(3-aminopropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminoprapyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-9~-methylthio-1.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(3-aminopropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl ) -maleini~nide ;
2-[1-(3-aminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5,~°dimethoxy-1H-indol~3-yl]-3-(1H~indol--3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(*)-2-[4-acetylamino-1-(3-ethoxy-2-hydroxyprapyl)-1H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)_~_[s-aGe~tylamino-~.-(~-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
(~)-2-[7-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-ma~leinimide:
(~)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(1-)-2-[6-amino-1-(3-ethoxy-2-hydroxypropyl)-li-I-indol-3°yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-amino-I-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[4-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]_ 3-(1H-indol-3-y1)-maleinimide;
(t)-2-[5-benzyloxy-1-(3-ethoxy-2-hydrdxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[6-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleini~mide;
(°1)-2-[7 -benzyloxy-1-(3-ethoxy-~-hydraxypropyl)-1H-indol-3-yl]-3-(1~EI-indol-3-yl)-maleinim3de:
(t)-2-[4-bromo-1-(3-ethoxy~2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(t)-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
-~6-(~)-2-[6-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-bromo-1-(3-ethoxy-Z-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(1-)-z-[~-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[6-chloro-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yI]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-fluaro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-ethoxy-2-hydraxypropyl)-6-fluaro-1H-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-fluoro-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydr~oxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(1Fi-indol-~-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~}-2-[1-(3-ethoxy-~-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl}-5-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(,1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methoxy-1H-indol-~-yl]-3-(1H-indol-3-y1)-maleinimide;
(-~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(1-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~}-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-z-[1-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy-1.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinim~,de;
(t)-2-[1-(3-ethoxy-2-hydroxypropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methyl-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methyl-IH-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methyl-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methyl-IH-indol-3-yl]°-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-vitro-IH-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(-~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(~)-2-[I-(3-ethoxy-2-hydroxypropyl)-s-vitro-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[1-(3-ethoxy-2-hydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[I-(3-ethoxy-2-hydroxyprogyl)-4-methylthio-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[I-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleini~ide;
(~)-2-[I-(3-ethoxy-2-hydroxypropyl)-6-methylthio-IH-indol-3-yl]-~-(IH-indol-3-yl)-maleinimide;
(~)-2-[1-(~~ethoxy-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(t)-2-[~,-(3~ethoxy~2~hydroxypropyl)-~,5-dimethoxy-1H-indol-3-yl]-3-(1H-indal~3-yl)-maleinimide;
(~)-2~[1-(3~ethoxy-2-hydroxypropyl)-5,6-dime~thoxy-IH-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-acetylamino-1-(3-ethoxy-2-hydrnxyp~opyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-acetylamino-1-(3-ethoxy-2-hydroxyp~opy~1)-1H-indal-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)°2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3°yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-amino-1~(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-['7-amino-1-(3-ethoxy-2-hydraxypropyl)-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(3-ethoxy-.2-hydraxypropyl)-iH-indol-3-yl]-3- ( ~.H-indol-3-yl ) -maleinim).de;
(-h)~2-[6-benzyloxy-1-(3°ethoxy-2-hydroxypropyl)-1H-indol°3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(3~ethoxy-Z-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
_5Q_ (+)-2-[4-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-Z-(~-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[6-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[5-chloro-1-(3-ethoxy-Z-hydroxypropyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide; v (+)-2-[6-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(~.H-indol-3-yI)-maleinimi.de;
(+)°2-[1~(3-ethoxy-2-hydroxypropyl)-4-fluoro-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~-[1-(3-ethoxy-2-hydroxypropyl)-6-fluoro-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethaxy-2-hydroxypropyl)-9-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropylj-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-~-hydroxyprapylj-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yI]-3-(iH-indol-3-ylj-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-7-trifluoromethyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-ylj-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropylj-5-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-?-methoxy-1H-indol-3~yl]-3-(1H-indol-3-yl)~-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydraxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
-5z-(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-6,7-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-.2-[1-(3-ethoxy-2-hydroxypropyl)--4-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-Z-hydroxypropyl)-6-methyl-iFd-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-~-hydroxypropyl)-5-vitro-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-vitro-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-vitro-iH-indol-3-y1]-3-(iH-indol-3-y1)-maleinimide;
(+)-~-[1-(3-ethoxy-2-hydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indo7.-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidea (+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
(-)-2-[b-acetylamino-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(_}-2-[7-aoetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-amino-1-(3-ethoxy-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol~3-yl)-maleinimide;
(-}-2-[6-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidei (-)-2-[?-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-( 1H-indol-3~yl ) -maleinimide;
(-)-~~[4~benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1FI-indol-3-y1)-maleinimide;
- 54 - ~~c)~~(9 (-)-2-[6-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-(7-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-bromo-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5--bromo-1°(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-bramo-1-(3-ethoxy-2-hydroxypropyl)-1H-indolp3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-(3-ethoxy-z-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(3-ethoxy-2-hydroxyprapyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[7-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-~iuoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro-iH-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-~luoro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-hydroxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-hydroxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methoxy-iH-indol-3-yl]-3-(lH~indol--3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(iH-i.ndol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
_56-(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(~.H-indol-~-yl)-maleinimide;
(-)-2-[Z-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy--1H- indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,7-methylendioxy-aH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(-}-2-[1-(3-ethoxy-2-hydroxypropyl}-5-methyl-1H-indol-~-yl]-3-(2H-indol-~-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-~-[1-(3-ethoxy-2-hydroxypropyl)-?-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl}~maleinimide;
(-)°2-[1-(3-ethoxy-2-hydroxypropyl)-6-vitro-1H-indol-3-y:L]-3-(1H-indol-3-y1)-maleinimideF
(-)-2-[~:-(3-ethoxy-2-hydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-x-hydroxypropyl)-4-methylthio-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[:1-(3-ethoxy-2-hydroxypropyl}-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 5? -(-)-2-[1-(3-ethoxy-~-hydroxypropyl)-6-methylthio-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,~-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yI]-3-(1H-indol-3~yl)-maleinimide;
(-)-~~[1-(3-ethoxy-2-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-acetylamino-1-(2-diethyZaminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[6-acetylamino-1-(2-diethylaminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-acetylamino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~4-amino-1-(~-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[5-amino-1-(2-diethylaminoethyl)-1H-indol~3-yl]-3-(1H-indol-3~yl)-maleinimide:
z-[6-amino~1-(2~diethylaminoethyl)-1H-indol-3~yl]~3-(1H-indol-~~yl)-maleinimide;
2-[7-amino-1-(2-diethylaminoethyl)-1H-indol~3-yl]-3-(1H-indol-3-yl)~maleinimide;
2-[4-benzyloxy-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
z-[5-benzyloxy-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-benzyloxy-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-benzyloxy-I-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1.-(2-diethylaminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[4-chloro-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[5-ahlaro-1-(2-diethylaminoethyl)-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[6-ahloro-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-[7-chloro-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-fluoro-1H-indol-~°yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-b-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
x-[1-(~-diethylaminoethyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-a-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-b-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-trifluoromethyl-2H-indol-3-yl]-3-(1H-indoi-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-b-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-trifluoromethyl-1H-indol-3-yI]-3-( 1H-indol-3-yl ) -maleinimide;
2-[~,-(2-diethylaminoethyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(~-diethylaminoethyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
60 _ i~~~ ~
2-[1-(2-diethylaminoethyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[1-(2-diethylaminoethyl)-7-methoxy-1H-indol-~-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(z-diethylaminoethyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(2-diethylaminoethyl}-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl}-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[1-(2-diethylaminoethyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-methyl-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(2-diethylaminoethyl)~4-vitro-1H~indol-3°yl]-3-(1H-indol-3-yl)-maleinimide;
2~[1-(2~diethylaminoethyl)-5-vitro~1H-indol-3-yl]~3~(1H-indol-3-yl)-maleinimide;
2~[1~(2~diethylaminoethyl)-6~nitra~1H~indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
2-[1~(2-diethylaminoethyl)~7-vitro-1H-indol-3~yl]-3-(1H-indol-3-yl)-maleinimide;
_, -61-2-[1-(2-diethylaminoethyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-methylthio-1H-indol-3-yl]-~-(1H-indol-~-yl)-maleinimide;
2 -[1-(2-diethylaminoethyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-acetylamino-~-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol- 3-yl)-maleinimide;
(~)-2-[5-aaetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-aaetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[7-acetylamino-1-(3-diethylamino-2-hydraxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-Z-[4-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(~)-2-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
a ~~~a ~a (--1)-2-[6-amino-1-(~-diethylamino-2-hydroxypropyl)-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø)-2-[7-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-benzyloxy-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(~.H-indol-3-yl)-maleinimide;
(~)-2-[7-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-~.H~-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-bromo-1-(3-diethylamino-2-hydraxypropyl)-1H-indol-3-yl]-3~(~.H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-bramo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[4-ahlara-1-(3-diethylamino-2-hydraxyprapyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(~)-2~[5-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(t)-2-[6-ahloro-1-(3-diethylamino-2-hydroxyprapyl)-3H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
__~, .- 6 3 -(~)-2-[?-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-~-hydroxypropyl)-5-fluoro-1H-indal-3-yl]-3-(~.H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamina-2-hydroxypropyl)-6~~fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-?-fluoro-1H-indol-3-yl]-3-(xH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(t)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-hydroxy-LH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1-)-~-[1-(3-diethylamino-2-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-?-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[1-(3-diethylamino-2-hydraxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-~-(1H-indol-3-yl)-maletnimide;
(t)-2-[1-(3-diethylamino-x-hydroxypropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-?-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl}-7-methoxy-1H-indol-3-y1J-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,~-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(--1)-2-[1-(~-diethylamino-2-hydroxypropyl)-6,7-methylendioxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-{3-diethylamino-2-hydroxypropyl}-4-methyl-1H-indol-3-yl]-3-(1H-indol~3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl}-5-methyl-1H-indol-3-yl)-3-{1H--indol-3-yl)-maleinimide:
(~)-2-[2-(3-diethylamino-2-hydroxypropyl)-6-methyl-1H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methyl-1H-indol-3-yl]-a-(1H-indol-~-yl)-maleinimide;
(t)~2~[1~(3-diethylamino-2-hydroxypropyl)-4~nitro-1H-indol~3-yl ] -3- ( ~.H~indol-3-yl ) -maleinimide;
(t)~2-[1-(3-diethylamino~2~hydroxypropyl)-5~nitro~1H-indol-3-yl]-3-(1H~indol-3-ylj-maleinimide;
(t)-2-[1-(3-diethylamina-2-hydroxypropyl)-6-nitro-1H-indol-3~
yl]~~~(1H-indol-3-yl)-maleinimide;
65 _ ~~~~~~~i (~)-2-[1-(3-diethylamino-2-hydrbxypropyl)-7-nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydraxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indal-3-yl)°maleinimide~
(--1)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[~.-(~-diethylamino-2-hydroxypropyl)-5,6-dimethoxy-3H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3°(1H-indol-3-yl)-maleinimide;
(+)-2-[4-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)~maleinimide:
(+)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)--2-[6-acetylamino-1-(3-diethylamino-2~hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[7-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-~-yl)-maleinimide;
(+)-2-[4-amino-1-(3-diethylamino-Z-hydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
-~~-(+)-2-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(+)-2-[6-amino-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-['3-amino-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-Z-[4-benzyloxy-1.-(3-diethylamino-x-hydroxypropyl)-1H-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide:
(+)-2-[t-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)~1H-~indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[:4-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-Z-[5-bromo-1-(~-diethylamino-2-hydroxypropyl)-1H-indol-~-ylj-3-(1H-indol-3-yl)--maleinimide;
(+)-2-[6-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol~3-ylj-3-(1H-indol-3-yl)-maleinimide;
(-H)-2-[~-chloro-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-~.-(3-diethylamino-2-hydroxypropylj-iH-indol-3-y1j-~-(xH-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(3-diethylamino-~-hydroxypropyl)-iH-indol-3-yl]-3-{1H-indol-3-y1)-maleinimidet (+)-2-[T-chloro-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yI]-3-{1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydraxypropyl)-~-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
{+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-fluoro-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-mal~inimide;
(+)-2-[1-(3-diethylamino-2 -hydroxypropyl)-7-fluoro-1H-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-hydroxy-iH-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-~-hydroxypropyl)--5-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamina-2-hydroxypropyl)-5-trifluoromethyl-iH-indal-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-trifluaromethyl-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
-~8-(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-trifluoromethyl-~.Fi-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyi)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2=hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(~-diethylamino-2-hydroxypropyl)-6-~methoxy-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-~methoxy-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-~)-2-[1-(3-diethylamino-Z-hydroxypropylj-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,s-methylendioxy-1H-indol-3-y1]-3-(2H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypr~pyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)'2-[1-(3-diethylamino-2-hydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-Z-[1-(3-diethylamino-2-hydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-3ndol-~-yl)-maleinimide;
(+)-2-[1~(3-diethylamino-2-hydroxyprapyl)-l-methyl-1H-indol-3-yl]-~-(1H-indol~3-yl)~~maleinimide:
(+)-2-[1-(3-diethylamino-a-hydroxypropyl)-~-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-s-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyi)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-methylthio-1H-indol-3-yI]-3-(1H-indol-3-yl)-~naleinimide:
(+)-2~[1-(3-diethylamino-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[Z-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-3H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3~-yl]-3-(1H-indol-3-yl}-maleinimide;
(+)-2-[1-(3-diethylamina-2-hydroxypropyl}-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-«)-2-[4-acetylamino-1-(3-diethylamino-2-~hydroxypropyl)-1H~
indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)--2-[6-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
-~o-(-)-2-(7-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(~-diethylamino-2-hydroxypropyl)-1H-ii7dol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-Z-[4-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-lH~indol-3-yl]-3-(1H-indol-3-yl)-maleinimid~;
(-)-2-[5-benzyloxy-7.-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-malei~nimide;
(-)-2-[4-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2~[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl~-3-(1H-indol-3-yl,)-maleinimide;
(-)-2-[6-bromo-1-(3-diethylamino-Z-hydxoxypropyl)-1H-indol-3-yl]-~~(1FI-indol-3-yl)-maleinimidm;
(-)-2-[7-broma-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
...., - m -(-)-2-[4-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(-)_2-[5-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl}-maleinimide;
(-)°2-[7-chloro-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-fluaro-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[x-(3-diethylamino-2-hydroxypropyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[1-(3-diethylamino-2-hydroxypropyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[~.-(3-diethylamino-2-hydroxypropyl}-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-~-hydroxy-1H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(~-diethylamino-~-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-}-2-[1-(3-diethylamino-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-tri~luoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-trifltaoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimids;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yI)-malsinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-~1-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-msthoxy-1H-indol-3-yl]--3-(1H-indol-3-yl)-malsinimide;
(-)-~-[1-(3-diethylamino-2-hydroxypropyl)-6-methoxy-~.H-indol-3-yl]-3-(1H-indol-3-y1)-maleirilmide;
(-)-2-[1-(3-disthylamino-2-hydroxypropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)~2°[1-(3-diethylamino-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-disthylamino-2-hydroxypropyl)-6,7-msthylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-methyl--1H-indol-3-yl]-3-(1H-indol-3-yl)-malsinimicle;
(-)-2-[1-(3-disthylamino-2-hydroxypropyl)-5-methyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-malsinimide:
(-)-~-[1-(3-diethylamino-2~hydroxypropyl)-6-methyl-1H-indol-3-yl~-3-(1H-indol-3-yl)-malsinimids;
_ 7~ _ ~~~ U
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methyl-1H-indol-3--yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[1-(3-diethylamino-2-hydroxypropyl)-~-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-nitxo-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-Z-hydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-vitro-iH-~indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)_~_methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(~-diethylamino-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methylthio-1H-indol-3-yl~-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl}-7-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-z-hydroxypropyl)-4,5-dimethoxy-1Ef-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[~.-(3-diethylamino-2~-hydroxypropyl}-5,6-dimethaxy-iH-indol-3-yl]-3-(1H-indol-3~-yl)-~maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl}-6,7-dimethnxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[4-acetylamina-1-(3-diethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-~4-2-[5-acetylamino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-acetylamino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-amino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[5-amino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-benzyloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-ben2yloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide:
2-[6-benzyloxy-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-benzyloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide:
2-[5-bromo-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
_, - 75 -2-[6-bromo-1-(3-diethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[4-chloro-1-(3-diethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~-chloro-1-(3-diethylaminopropyl}-1H-indol-3-yl]-3-(~.H-indol-3-yl}-maleinimide;
2-[6-ahloro-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-(1.-(3-diethylaminopropyl)-4-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl}-6-fluaro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1~(3-diethylaminopropyl)-4~hydroxy-1H~indol-3-yl]-3-(~.H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[~.-(3-diethylaminopropyl)-~-hydroxy-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-hydroxy-1H-°indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-trifluoromethyl-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[3.-(3-diethylaminopropyl)~6-trifluoromethyl-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-7-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl}-4-methoxy-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopxopyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5,~-methylendioxy-1H-indol-:3-yl]-3-(1H-indol-3-yl}-maleinimide:
2-[1-(3-diethylaminopropyl)-6,7-methylendiaxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methyl-1H-indol-3-y1]-3-(1H-indol-:i-yl)-maleinimide:
~.._, - ~~ -2-[1-(3-diethylaminopropyl)-6-methyl-1H-indol-3-yl]-s-(a.H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(a°diethylaminopropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-6-vitro-1H-indol-3-yl]-3-(LH-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep 2-[3,-(3-diethylaminopropyl)-9--methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-5-methylthio--1H-indol-3-yl]~3-(1H-indol-3-yl)-~maleinimide:
2-[2-(3-diethylaminopropyl)-6-methylthio-1H-indol-3-yl]--3-(1H-indol-3-y1)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[2-(3-diethylaminopropyl)-4,5~dimethoxy-1H-indol-3-yl]-~3-(1H-indol-3-yl)-maleinimide:
2-[1-(~-diethylaminapropyl)-5,6-dimethoxy-1H-indoi-3-yl]-3-(1H-indol-3-ylj-maleinimide;
2-[1-(3-diethylaminopropyl)-c,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~~.J~~~' _ ,8 _ 2-[4-acetylamino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[5-acetylamino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[?-acetylamino-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3--y1)-maleinimide;
2-[?-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-benzyloxy-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[7-benzyloxy-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-ethylaminopropyl)-1H-$ndal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
~w~
_ 79 2-[5-bromo-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-ethylaminopropyl)-iH-indol-3-yl?-~-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[4-chloro-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-ethyiaminopropyl)-iH-indol-3-yl]-3-(iH-:indol-3-yl)-maleinimide;
2-[7-ahloro-1-(3-ethylaminopropyl)-iH-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-~-fluoro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-fluaro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
z-[1-(3-ethylaminopropyl)-7-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[1-(3-ethylaminopropyl)-4-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-$Q-2-[1-(3-ethylaminopropyl)-6-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol--3-yl)-maleinimide;
2-[I-(3-ethylaminopropyl)-4-trifluoromethyl-1H-indol-3--yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-trifluaromethyl-1H-indol-3-yl]-3-( 1H-indol-3-yl) -maleir~imide;
2-[1-(3-ethylaminopropyl)-7-trifluoromethyl-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4-methoxy-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-methoxy-2H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-methoxy-2H-indol-3-yl]-3-(1H-~indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4,5-methylendioxy-1H-indol-3-y1]-3-( 1H-indol-3-yl ) -maleinimide;
2-[2-(3-ethylaminopropyl)-5,6-methylendioxy-1H-indol-~-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-2-[Z-(3-ethylaminoprapyl)-4-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-f>-methyl-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethyl.aminopropyl)-7-methyl-1H-indol--3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(3-ethylaminopropyl)-4-vitro-iH-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4-methylthio-3H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methylthio-1H-indol-~-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-methylthio-iH-indol-3-yl]-~~-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-methylthio-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylam.inopropyl)-4,5-dimethoxy-1H-indol-~-yl]-3-(1H-indol-3-yl ) -malei~rimide;
- g2 - ~v:~~~~~
2-[1-(3-ethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
a-[a.-(3-ethylaminopropyl)-6,7-dimethoxy-1H-indol-3-yl]-~-(~.H°
indol-3-yl)-maleinimide;
(f)-2-[4-acetylamino-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-Z-[6-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
(~)-2-[4-amino-1-(2-hydroxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-benzyloxy-~.°(2-hydroxy-3-dimethylaminoprapyl)-1FI-indol-3-yl]_3-(iH-indol-3-yl)-malein~.mide;
(t)-2-[5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-~.H-indol_3-yl]-3-(~.H-indol-3-yl)-maleinimide;
~3 -(~)-2-[7-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3~
yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[6-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-bromo-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)°~maleinimide;
(~)-2-[5-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[6-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-~-(iH--indol-3-yl)-male3nimide;
(~)-2-[4-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[5-~luoro-1-(2-hydroxy-3-dimethylamia~opropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[6-~luoro-~,--(2-hydroxy-3-dimethyl~minopropyl)-1H-indol-3-yl]-a-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-~1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
- 8~ -(~)-2-[4-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[6-hydroxy-1-(2-hydroxy-3-dimethylaminopxopyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1.H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(--1)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-2-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydraxy-~-dimethylaminopropyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminapropyl)-5-methoxy-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(f)-2-[1-(2-hydroxy-a-dimethylaminopropyl)-4,5-methylendioxy-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 85 - .~ ~ J ~~
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[1-(2-hydroxy-3-dimethyiaminopropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-~5-methyl-1H-indol-3-yl]-3-(1H-indol-~-yl)°maleinimide;
(-i-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methyl-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(a-hydroxy-3-dimethylaminopropyl)-4-vitro-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminogropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~y-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-a-yI]-3-(1H-indol-3-yl)-maleinimide;
(i)-2-[~.-(2-hydroxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1.-(2-hydroxy-3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol°3-yl)-maleinimide;
(ø)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol -3-yl)-maleinimide:
(+)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[6-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[7-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-amino--1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
(+)-2-[5-amino-1-f,2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+}-2 -[6-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7 -amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~--yl)-maleinimide:
(+)-2-[4-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~-y1)-maleinimide:
-(+)-2-[5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(+)-2-[s-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(+)-2-[7-benzyloxy-1-(~-hydroxy-3-dimethylaminoprapyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol--3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-bromo-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(~-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(+)-~-[4-ahloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(~-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(+)-2-[6-ahloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chlora-1-(~-hydroxy-3-dimethylaminoprapyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-fluoro-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-~-dimethylaminopropyl)-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
_88_ (+)-2-[6-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)--1H-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-Z-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-:indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)~iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[~-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(+)-2-[?-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
(*)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-+~)-2-[1~(2-hydroxy-3-dimethylaminopropyl)-5-methoxy-1H~indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(*)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-malelnimide;
(+)-2-[1-(2-hydroxy-~-dimethylaaninopropyl)-7-methoxy-7.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[1-(2-hydroxy-3-dimethylaminogropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(~.H-indol-3-yl)-maleinimide:
(+)-2-[7.-(2-hydroxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl ] -3- ( 3.H-indol-3-yl ) -maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-y1]-3-(1H-indol-3-y1)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methyl-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methyl-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminoprapyl)-7-methyl-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)--~-[1-(2-hydroxy-3-dimethylam~.isopropyl)-6-vitro-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinirnide:
(+)-2-[~.-(2-hydroxy-3-dimethylaminopropyl)-7-vitro-1I~I-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[~.-(2-hydroxy-a-dimethylaminopropyl)-4-methylthia-1H-indol-3-yl)-3-(1H-indol-3-yl)-male9.nimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-dimethoxy-1H°
indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(_)_~_[~_acetylamino-1-(2-hydrdx~-~-dimethylaminapropyl)-1H-indol--3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinim~.de;
(-)-2-[7-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)--iFi-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-amino~1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol~3-yl]-3-(1,H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2-hydroxy-3-dimethy~.am3nopropyl)-iH-indol-3-y1]-3-(~.H-indol-~-yl)-maleinimide:
(-)-2-[6-amino-1-(2-hydroxy-3-dimethylaminopropyl)-a.H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
- ~~.~.c'~~~~J
(-)-2-[7-amino-~.-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3- ' yl]-~-(1H-indol-3-yl)-maleinimide;
(-)-2-[~-benzyloxy-1-(2-hydraxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydraxy-3-dimethylaminopropyl)-iH-indal-3-yl]-3-(2FI-indol-3-yl)-maleinimide:
(-)-2-[6-benzyloxy-1-(2-hydraxy-3-dimethylaminaprapyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indal°3°yl)-maleinimide;
(-)-2-[4-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-d~.methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)~2-[5-chloro-1-(2-hydraxy-3-dimethylaminoprapyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(~)-2-[6-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(-)-2-[7-chlora-1-(2-hydroxy-3~dimethy~.aminapropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-. 9 2 --(-)-2-[4-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol--3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[6-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[7-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[6-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[7-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)_iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[4-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3_yl]-3~(1H-indol-3-yl)-maleinimide:
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maieinimide:
(-D-2-C6-trifluoromethyl-1-(2-hydroxy-3-dimethylaminoprapyl)~
1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[T-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-fndol-3-yl]-3-(1H-indal-~-yl)-malainim3de:
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methoxy-1H-indol-3-yl]-3~-(1H-~indol-3-yl)-maleinimide;
- 93 - ~r~~?~~~
(-)-2-[1-(2-hydraxy-3-dimethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)°maleinimide;
(-)°2-[1-(~-hydroxy-3-dime~thylaminopropyl)-6-methoxy-1H-indol--3-y1]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[1-(2-hydroxy-3-dimethylaminoprapyl)--4,5-methylendioxy-~.H-indol-~-yl]-3-(1H-indoi-3-yl}-maleinimide;
(_)_2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methyl-1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
(_)_2_[1.:(z-hydroxy-3-dimethylaminopropyl)-5-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydraxy-3-dimethylaminopropyl)-4-vitro-iH-indal-3-yl]-~-(1H-indol-~-yl)-malein3,mide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-iH-indol-a-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- u~ ~" ~, ,r.
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-nitra-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-2H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)~2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylama.nopropyl)-6,7-dimethoxy°iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-acetylamino-1-(2-hydroxy-3-(~1-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2-hydroxy-3-(4-morphalino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)~2~[7-aaetylamino-1-(2-hydraxy-3-(4-morpholino)prapyl)-1~I-indol-3-yl]~3-(1H-indol-~-yl)-maleinimide;
(t)-2-[4-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-~5-(~)-2-[5-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[6-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl}-iH-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(~)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-benzyloxy-1-(Z-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3°(1H-indol-3-yl)-maleinimide:
(~)-2-[7-benzyloxy-1-(~-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
{~)-2-[4-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(*)-2-[6-bromo-1-(2-hydroxy-3-{4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-broma-1-(2-hydroxy-~-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2~[4-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-2H-indol-3-yl]-3-(~.H-indol-~-yl)-maleinimidet (~)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-.lgi-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(ZH-indol-3-yl)-maleinimide;
(~)-2-[6-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1-)-2-[7-fluoro-1-(2-hydroxy-3-(4amorpholino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-hydroxy-1-(2-hydroxy-3-(~-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maie.inimide;
(~)~2-[5-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-i-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-hydroxy-~-(4-morpholino)propyl)-~.H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(i-)-2-[6-trifluoromethyl-1-(2-hydroxy-~-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~n .~, ~?
(~)°2-[7-trifluoromethyl-1-(2-hydroxy-3-(4-morpholina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep (~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimidet (~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-1H-indol--3-yl]-3-(iH-indol-3-yl)-maleinimidet (~)-2-[1-(~-hydroxy-3-(4-morpholino)propyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-methylendioxy_ 1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morphalino)propyl)-4-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methyl-1H-:Lndol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(a-morpholino)propyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-vitro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-nitre-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-G-nitro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydraxy-3-(4-morpholino)propyl)-7-nitre-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(~-morpholino)propyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-methylthio-1H-indol-3-yl]-3-(7.H-indol-3-yl)-maleinimide;
(~)-Z-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(Z-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(*)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-~-yl)°maleinimide;
(*)-2-[4-acetylamino-1-(2-hydraxy-3-(~-marphalino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(*)-x-[5-acetylamino-1-(2-hydroxy-3-(~-mnrpholino)propyl)-1H-~.ndol-3-yl]-3-(1H-indol-3-yl)-maleini~n,ide;
(+)-2-[6-acetylamino-1-(2-hydroxy-3-(~-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
((~~ ~9; ~,A~
- ~ ~ ~ eJ~ Q.
(+)-2-[7-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-{2-hydroxy-3-(4-morpholino)propyl)-1Ii-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[~-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3°yl]-3-(1H-indol-3-yl)-maleinimides (+)-2-[6-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-hydroxy-3-{~-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+) -2- [ 5-bromo-1- ( 2-hydroxy-3- { ~-morphol ino) propyl ) -1Fi-indol-3-y1]-3 -(iH-indol-3-yl)-maleinimide;
(+)-Z-[6-bromo-1-(2-hydroxy-3-(~6-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(2-hydroxy-3-(4-morpholino)propy:l)-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
o - ~~r~
(+)-2-[~-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol~
3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chloro-1-(2-hydroxy-3-(4-morpholina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~-[4-~luoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-2H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(+)-2-[7-~luoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-hydroxy-Z-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-2-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(1H-indo~.-3-yl)-~naleinimidet (+)-2-[7-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(+)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(~-morpholino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[6-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl}-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide:
(+}-2-[7-trifluoromethyl-1-(2-hydroxy-3-(~-morpholino)propyl}-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-marpholino)propyl)-6-methoxy-iH-indol-3-yl]-3-(IH-indol-3-yl}-maleinimide:
(+)-2-[1-(2-hydroxy-~-(~-morphoiino)propyl)-7-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(~-hydroxy-3-(4-morpholino)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-z-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-methylendinxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methyl-iH°-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morphcalino)propyl)-5-methyl-iH-indol-3-yl]-3-(iH-indol-3--yl)-malein~.mide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-methyl-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydraxy-3-(4-morpholino)prapyl)-7-methyl-1H-indol-3-y1]-3t-(1H-indol-3-yl)-maleinimide:
(+)-2-[1~-(2-hydraxy-3-(4-morpholino)propyl)-4-nitra-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-vitro-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholina)propyl)-7-vitro-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-methylthia-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)~maleinimide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(+}-2-[1-(2-hydroxy-3~(4-morpholina)propyl)-5,6-dimethoxy~1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-dimethaxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-acetylamino-1-(2-hydroxy-3-(4-marpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(h-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(°)°2-[7-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-}-2-[5-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-amino-1-(2-hydroxy-~-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[7-amino-1-(2-hydroxy-3-(4-morpholino}propyl}-1H-indol«3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[4-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-i~enzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[s-benzyloxy-1-(Z-hydroxy-3-(4-morpholino)propyl}-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(-)-2-[7-benzyloxy-1-(2-hydroxy-3-(4-morpholino}propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-}-2-[4-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholino}propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
;., - log -(_)_2-[6-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[7-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)~-2-[4-chloro-1-(2-hydroxy-3-(4-morphalina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-chloro-1-(2-hydraxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[6-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
(-)-2-[7-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-fluoro-1-(2-hydroxy-3-(~-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide:
(-)-2-[5-fluoro-1-(2-hydroxy-3-(4-morphalino)propyl)-iH-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide:
(-)-2-[6-fluoro-1-(2-hydraxy-3-(4-marpholina)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-fluoro-1-(2-hydroxy-3-(~-marpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-hydraxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-hydroxy-1-(Z-hydroxy-3-(4-marpholino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide:
(-)-2-[~-hydroxy-1-(2-hydroxy-3-(4-morpholina)prapyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[7-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2-hydroxy-3-(4~~morpholino)propyl)-1H-indol-3-yl)-3-(1H-indol-~-yl)-maleinimide;
(-)-2-[7-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholin~)propyl)-4-methoxy-1Fi-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(-)-2-[1-(2-hydraxy~3-(4-morpholino)propyl)-5-methaxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-G-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morphalino)propyl)-7-methoxy- 1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-methylendioxy-1H-indal-3-y1)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-marphalino)propyl)-5,G-methylendioxy-1H-indol-3-yl)-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-marphalino)propyl)-G,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methyl-1H-indol-3-yl]-a-(1H-indol-3-yl)-maleinimide;
- so6 -(-)-2-[1-(2-h.ydroxy-3-(4-morpholino)propyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(~°morpholino)propyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-?-methyl-1H-indol-3-yl]-3-(1H--indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1~(2-hydroxy-3-(4-morpholino}propyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-vitro-1H-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-?-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-~-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-1H-indol-3-yl]-3-(~H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morphalino)propyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-?-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinim3.de;
(-)-2-[1-(2-hydroxy-3-(4-morpholino}prapyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
- to (-)-2-[1-(~-hydroxy-3-(4-morphalino)propyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(--1)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[6-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-raaleinimide:
(~)-2-[7-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[6-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(_+)-2-[7-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H°-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[4-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)~-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(a)-2-[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)~-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~j-2-[6-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[7-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indal-3-yl]-3-(2H-indol-3-y1)-maleinimide:
- zo~ - ~:~~J~
(~)°2-[4-bromo-1-(2-hydroxy-3-(1-piperidino}propyl)-3.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo~1-(2~hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-bromo-1-(2-hydroxy-3-(1-piperidino}propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[7-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[4-chloro-~.-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
(~)-2-[5-chloro-1-(2~hydroxy-3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[6-chloro-1-(2-hydroxy-3~(1-piperidino)propyl)-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(2-hydroxy-3-(1~piperidino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)~maleinimide;
(~)-2-[4-fluoro-1-(2-hydroxy-3-(1~piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(2-hydraxy-~-(1-piperidino}propyl}-1H-indol-3-yl]-3~(1H~indol-3-yl)-maleinimide;
(t)-2~[6-fluoro-~.~(2~hydroxy-3~(1~piperidino)propyl)-1H-indol-3~yl]~3~(1H-indol~3~yl)-maleinimide;
(t)~2~['7~fluoro~2-(2-hydroxy~3~(~.-piperidino)propyl)~1H~indol-~-yl]-3-(1H-indol~3-yl)-maleinimide;
(t)-2-[4-hydroxy~1-(2-hydroxy~~~(1~piperidino)propyl)~1H~indol-3-yl]-3-(~.H~indol-3~yl)-maleinimide;
- to (--1)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[7-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3~y1)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-trifluoromethyl-1-(z-hydroxy-3-(~.-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(1)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[~.-(2-hydroxy-3-(1-piper].dino)propyl)-7-mathoxy-1H-indol-~-yl~-3-(iH-indol-3-yl)-maleinimide:
(~)-~-[1-(2-hydroxy-3-(1-piperidino)propyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,C-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
- llfl -(~)-2-[1-(2-hydroxy-3-(1-piperidino}propyl}-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-~-methyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[~.-(2-hydroxy-3-(1-piperidino}propyl)-5-methyl-1H°indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[2-(2-hydroxy-3-(1-piperidina}propyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[1-(~-hydroxy-3-(1-piperidino)propyl}-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide~
(~)-2-[1-(2-hydroxy-3-(~.~piperidino)propyl)-4-vitro-1H-indol-3-yl]-3-(3H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-~5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-vitro-1.H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methylthio-1H~
indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(1-piperidino)prapyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-.3-yl)-maleinimide~
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinirnide;
(v)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
- 111 - ~~e (~)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-4,5-dimethoxy-iH-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-z-[1-(z-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-6,7-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-acetylamino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-acetylamino-1-(z-hydroxy-3-(1-piperidino)propy~.)-iH-indol-3-yl.]-3-(iH-indoi-3-yl)-maleinimide;
(+)-2-[7-acetylamino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-z-[4-amino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-amino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimiua;
(+)-2-[7-amino~1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-z~[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
- 112 ° ~) e) ~ ~ ' (+)-2-[6-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(2-hydroxy-3-{1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~2-[7-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(2-hydroxy-3-{1-piperidino)propyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleiniinide;
(+)-2-[7-chloro-1-(2-hydroxy-3-{1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-~-(1-piperidino)propyl)-1H-indol-3-yl]-~-(1H-indol-~-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-ms-(+)-2-[7-fluoro-1-(2-hydroxy-~-(7.-piperidino)propyl)-1H-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(+)-2-[~3-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-hydroxy-1-(2-hydraxy-3-(1-piperid:Lno)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(~.-piperidino)propyl)-1H-indol-3-yl]-3-(1N-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-3.-(2-hydroxy-3-(2-piperidino)propyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-trifluoromethyl-Z-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol°3-yl]-3-(1H°indol-3-yl}~maleinimide;
(+)-2-[1-(2-hydroxy-a-(1-piperidino)propyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-x-[1-(2-hydroxy-3-(5.-piperidino)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2~[1-(2-hydroxy-3-(1-piper].dino)propyl)-6-metkioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy~3-(1-piperidino)propyl)-7-methoxy-2H-indol~
3-y1]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,~-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[~.-(2-hydroxy-3-(1-piperidino)propyl}-6,7--methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(+)-2-[1-(2-hydroxy-3-(1-piperidino)progyl}-6-methyl-iH--indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(+j-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-7-methyl-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+}-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-vitro-iH-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-6-vitro°1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet (+)-2-[1-(z-hydroxy-3-(1-piperidino)propyl}-7-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinim:Lde;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+) -2- [ 1- ( 2-hydroxy.-3- ( 1-piperidino) propyl } --5-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-methylthio-1H-indol-3-yl]-3 -(1H-indol-3-yl)-maleinimider (+)-2-[1-(2-hydroxy-~-(1-piperidino)propyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)prapyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[7-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-~-[4-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[s-amino-1-(2-hydroxy_3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[~-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(~-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)~2-[5-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]~~3-(1H-indol-3-yl)-maleinimide;
(-)-2-[f-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-(2-hydroxy-~-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(~-hydroxy-3-(1-piperidino)propyl)-iH-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propylj~lH~indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-chlaro-1-(2-h:ydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)~2-[7-chloro~1-(2-hydroxy-3~(1-piperidino)propyl)-1H-indol-~-yl]~3~(1H-indol~3-yl)~maleinimide;
(-)-2-[4-fluoz~o-1~(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
- 11? -(-)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-fluoro-1-(2-hydroxy-3-(~.-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-hydroxy-1-(2-hydroxy-3-(1-piperldino)prapyl)-?._ hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methaxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[~.-(2-hydraxy-3-(1-piperidino)propyl)-5-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
L m, - ms -(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-s-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,s-methylendioxy-1H-indol-3-y1]-3-(1H-indol-3-yl}-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(_)-2-[1-(Z-hydroxy-3-(1-piperidino)propyl}-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)_~_[1-(2-hydroxy-3-(1-piperidino)propyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-~-vitro-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1~(2-hydroxy-3-(1-piperidi.no)propyl)-5~nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-}-2-[1-(Z-hydroxy-3-(1-piperidino)propyl)-s-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-) -2- [ 1- ( 2-hydroxy-3- ( ~.-piperidino} propyl ) -7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
- 119 - ~~~~~.e (-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimidea (-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(-)-~-[1-(2-hydroxy-3-(1-piperidino)propyl}-7-methylthio-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide:
(-)°2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-dimethoxy-iH-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(°)-2-[1-(2-hydroxy-3-(1-piperidina)propyl)-5,7-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-~)°2-[4-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-mal~inimide;
(~}-2-[6-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimideo (t)-2-[7-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
(i)-2-[4-amino-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
- 1~0 - ~~.°~~' (--1)-2-[6-amino-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(~)-2-[7-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø)-2-[4-benzyloxy-1-(~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-~)-B-[6-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[4-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(--1)-2-[6-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(1-)-2-[7-bromo-1-(~,3-dihydroxypropyl)-iH-indol-3-yl]-3-~(iH-indol-3-yl)-maleinimide;
(t)-2-[4-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(:~)-2-[5-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[6-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 1~1 -(~)-2-[7-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(--1)-2-[4-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(~,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1)-2-[6-fluoro-1-(2,3-dihydroxypropyl}-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-fluora-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-hydroxy-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(ø)°2-[5-Ydydroxy-1-(2,3-dihydroxypropyi)-1H-indol-3-yl]-~3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2,3-dihydroxypropyl)--iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2,3-dihydroxypropyl)-1H-indal~3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t}-2-[5-trifluaromethyl-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-3~ndo1-3-yl)-maleinimide;
(~)-2~[6-tr:Lfluoromethyl~1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-1-(2,3-dihydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-di.hydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol -3-yl]-3°{1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2,3-dihydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1-)-2-[1-{2,3-dihydroxypropyl)-7-methoxy-1lH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[1-(2,3-dihydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-6,3-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(ø)-2-[1-{2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
{~)-2-[1-(2,3-dihydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(t)-2-[1-(2,3-dihydroxypropyl)-?-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4-nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-Cl-(2,3-dihydroxypropyl)-5-nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-6-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-?-vitro-iH-indol-3-yl]-3-(1H-indol-3-yi)-maleinimide:
(--1)-2-[1-(2,3-dihydroxypropyl)-4-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-lI-I-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-6-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(--1)-2-[1-(2,3-dihydroxypropyl)-?-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-2H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-5,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-6,?-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+}°2-[4-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[6-acetylamino-~.-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide:
(+)-2-[?-acetylamino-1-(2,3-dihydroxypropyl)-1Fi-indol-3-yl]-3-(1H-indol-3-yl)mmaleinimide:
(+)-2-[4-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+}-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+}°2-[6-amino-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(1H-indal-3-yl}-maleinimide;
(+)-2-[7-amino-1-(2,3-dihydroxypropyl)-1H-indol-°3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[S-benzyloxy-1-(2,3-dihydroxypropyl}-iH-indol-3-yl]-3--(1H-indol-3-yl)-maleinimide;
(+)-2-[6-benzyloxy-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(+}-2-[5-bramo-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(1H-indal-3-yl)-maleinimide;
(+)-2~[6-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2~[7-brama~1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-chloro-1-(2,3-dihydroxypropyl}-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
- 125 - ~.~c~s~~~s (+)-2-[5-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[s-chloro-1-(2,3-dihydroxypropylj-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+j-2-[4-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3~yl]~3-(1H-indol-3-yl)-maleinimide:
(+j-2-[5-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3--yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2,3-dihydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimidei (+)-2-[7-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-hydroxy-1-(2,3-dihydroxypropylj-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[s-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]~-3-(1H-indol-3-yl)-maleinimide:
(+j-~-[7-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]--3-(1H-indol-3-yl)-maleinimide;
(+)-2-r4-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimida;
(+)-2-[5-trifluoromethyl-1-(2,3-dihydroxyprapyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- las -(+)-2-[6-trifluoromethyl-1-(z,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-trifluoromethylai-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep (+)-2-[1-(2,3-dihydroxypropyl)-4-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-s-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)~-2-[1-(2,3-dihydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(~,3-dihydroxypropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide~
(+)°2-[1-(2,3-dihydroxypropyl)-°5,6-methylendioxy-1H-indol-3°
yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[1-(2,3-dihydroxypropyl)-6,7-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[1-(2,3-dihydroxypropyl)-~-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet (+)-2-[1-(2,3-dihydroxyprapyl)-5-methyl-iH-inds~l-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3~dihydroxypropyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimideo (+)-2-[1-(2,3-dihydroxypropyl)-7-methyl-iH-indol-3-yl]-s-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihyc~roxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[2-(2,3-dihydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimida;
(+)-2-[1-(2,3-dihydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-7-methylthio-1H-indol-3-yl]-3--(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydraxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[~.-(2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(_)-2-[4-acetylamino-1-(2,3-dihydroxypropyl)--1H-indol-3-y1]-3-(1H-indol-3-y:l)-maleinimide;
(-)-2-[5-acetylamino-1-(~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 12$ - ~.~e.~e~~
(-)-2-[6-aoetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[7~-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[4-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-amino°1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[6-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimideo (-)-2-['7-amino-1-(2,3-dihydroxypropyl}-1H-indol-3-y1J-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-benzyloxy-1-(2,3-dihydraxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(2,3-dihydroxypropyl)-lH~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(-)-2-[4-bromo-2-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[5-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-y1]-3-(1H-indal-3-y1)-maleinimidef (-)-2-[6-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
ed - 1~9 - l~ ~~2' ~~~;~
(-)-2-[?-bromo-1-(2,3-dihydroxypropyl)-1H-indol -3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[?-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-gluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-gluoro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-gluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-gluoro-1-(~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-inc~ol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-{~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-13~-(-)-2-[4-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1~(z,3-dihydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(1H-indol~-3-yl)-maleinimide;
(-)-~-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-Z-[1-(2,3-dihydroxypropyl)-6,7-methylendioxy-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-(1-(2,3-dihydroxypropyl)-~-methyl-iH-indol-3-yla-3-(iH-indol -3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 131 - ~ e~
(-)-2-[1-(2,3-dihydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-~-[1-(2,3-dihydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(_)_2_[1_(2,3-dihydroxypropyl)-7-vitro-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)°2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(2H-indol-3-yl)-~naleinimide;
(-)_2-[1-(2,3-dihydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indo2-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-7-methylthio-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--)_2-[1-{2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-G,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleiniznide;
.. 132 - ~~_~~:~~a 2-[4-acetylamino-1-(3~-hydroxypropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino°1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[?-amino-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(5-benzyloxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-benzyloxy-1~(3-hydroxypropyl)-1H~indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[7-benzyloxy-1-(3-hydraxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;.
2-[5-bromo-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-ohloro-1-(3-hydroxypropyl)-1H-indol-3~-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-hydroxypropyl)~-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-chloro-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-hydroxypropyl}-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[5-fluoro-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
~-[7-fluoro-1-(~-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[5-hydroxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
13~ -2-(6-hydroxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[?-hydroxy-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-hydroxypropyl)-5~~trifluaromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-hydroxypropyl)-6-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[?-trifluoromethyl-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-f>-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-?-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)--maleinimide;
~-[1-(3-hydroxypropyl)-4,5-methylendioxy-1H~indol-3-yl]-3-(1H-indol-3-yly-maleinimide;
2-(1-(3-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6,?-methylendiaxy-1H-indol-3-yl]-3-(lI-I-indol-3-yl)-maleinimide;
- 13 5 - ~ 'e,n~' 2-[1-(3-hydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(iH-indol~3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
z-[1-(3-hydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol--3-yl)-maleinimide;
2-[1-(3-hydroxyprapyl)-6-methylthio-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~.~(3-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~~:~ ~~_ 2-[Z-(3-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-[4-acetylamino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-[6-acetylamino-7.i(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
Z-[7-acetylamino-1-(3-isothiocyanatopropyl)-1H-indc~l-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-amino-1-(3-isothiocyanatopropyl)-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide:
2-[5-amino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]°3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1.-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[7-amino-2-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[4-benzyloxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-iso~thiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[6-benzyloxy-1-(3~isothiocyanatapropyl)-1H-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-1-(3-~.sothiacyanatopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-isothiocyanatopropyl)-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[7-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-isothiacyanatapropyl)-1H-indal-3-yl]-3-°(1H-indol-3-yl)-maleinimide;
2-[5-chlora-1-(3-isothiacyanatoprapyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-chlaro-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-isothiocyanatopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-isothiocyanatoprapyl)-1H-indal-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[5-fluoro-1-(3-isothiacyanatoprapyl)-1H-indol-3-yl]-3-(1H-indal-3-yI)-maleinimide;
2-[6-fluoro-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-fluoro-1-(3-isathiocyanatapropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(3-isothiocyanatopropyl)-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[5-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3~[1-(3-isothiocyanatopropyl)-4-methoxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-methoxy-1H-indol-3-yl]-maleinimide;
2-(1.H-indol-3-yl)-3-(1-(3~isothiocyanatopropyl)-6-methoxy-1H-indol-3-yl]-maleinimida;
~-(1H-indol-3-yl)-3~[1-(3-isothiocyanatopropyl)-7-methoxy-1H-indal-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
c'?, , i ~~ .~ e~ J
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
z-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-s,~-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[~.-(3-isothiocyanatopropyl)-4-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-6-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yI)-3-[1-(3-isothiocyanatopropyl)-7-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2 -(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-6-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-7-vitro-1H-indol-3-yl]-maleinimide;
2-(1H~indol-3-y1)-3-[1-(3-isothiocyanatopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-methylthio-1H-indol-3-yl]--maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isathiocyanatopropyl.)-6-methylthio-1H-indol-3-yl]-maleinimide;
~~~~vd a-2-(1H-indol-3-yl)-3-[1-(3-ZSOthiocyanatopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4,5-dimethoxy-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5,6-dimethoxy-1.H-indol-3-yl]-maieinimide:
2-(~.H-indol-3-yl)-3-(1-(3-isothiocyanatopropyl)-s,7-dimethoxy-1H-indol-3-yl]-maleinimide:
(~)-2-[4-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-acetylamino-1-(2-methoaty-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide:
(~)-2-[6-acetylamino-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-['7-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-~-(5-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-mal~inimide:
(~)-~-(6-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl~-3-(1FI-indol-3-yl)-maleinimide;
(t)-?.-[7-amino-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[4-benzyloxy-~.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(*)-2-[6-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(~)-2-[7-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-~)-2-[4-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
(~j-2-[6-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[7-bromo-1-(2-methoxy-3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-1nd01-3-ylj-maleinimide;
(i)-2-[4-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-ylj-maleinimide:
(~)-2-[6-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-Z-[7-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-~luoro-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
_ 142 -(--1)-2-[6-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[4-hydroxy-3-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-iH--indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-~aleinimide;
(~)-2-[6-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H°indol--3-yl]-~-(1H-indol-3-yl)-maleinimide;
(t)-2-(1H-indol-3-yl)-3°[4-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(t)-2-(1H-indol-~-yl)-3-[~-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-maieinimide;
(~)-2-(1H-indol-3-yl)-3-[6-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-maleinimide;
t j - 143 - ~,~.~~i~~~~
(~)-2-(1H-indol-3-yl)-3-[7-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(x-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-(1-(2-methoxyp3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy~-3-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-maleinimide:
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-y1)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methyl-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methyl-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-nitro-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-m~thoxy-3-dimethylaminopropyl)-5-nitro-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-nitro-1H-indol-3-yl]-maleinimide;
(t)-2-(1H-indol-3-yl)-3-[1-(z-methoxy-3-dimethylaminopropyl)-7-nitro-1H-indol-3-y1]-maleinimide;
(t)-2-(1H-indol-3-y1)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide;
~r~~~=
- 1~4 -(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(--1)-2-(1H-indol-3-yl)-3-[6,7-dimethoxy-i-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-[4-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-I-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[7-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-amino-1-(2-methaxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-amina-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-benzyloxy-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~-[7-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-bromo-1-(2°methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(+)-~-[7-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-~-(1H-indol-3-yl)-malei.nimide;
(+)-2-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(2-methoxy-3-dimethylam~.nopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-ahloro-~.-(2-methoxy-3-di.methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-fluoro-1-(2-methoxy-~-dimethylaminopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-methoxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[7-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-y~.]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-trifluoromethyl-3.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
(+)-z-(7-trifluoromethyl-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[4-methoxy-1-(2-methaxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
-, - 14? -(+)-2-(1H-indol-3-yl)-3-[5-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-~-[6-methoxy-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2 -(iH-indol-3-yl)-3-[?-methoxy-1-(2-methoxy-~-dimethylaminopropyl)-1H-indoi-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5,6-methylendioxy-iH-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6,?-methylendioxy-iH-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-y1)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-:3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methyl-iH-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-?-methyl-1H-indol-3-yl]-maleinimide;
(+)~2~(1H-indol-3~yl)-3~[1~(~-methoxy-3-dimethylaminopropyl)-4-nitro-iH-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-nitro-iH-indol-3-yl]-maleinimide;
(+)-~-(iH-indol-3-yl)-3-[1-(~-methoxy-3-dimethylaminapropyl)-6-nitro-1H-indol-3-yl]-maleinirnide;
~w~_~a~~J
(+)-2-(1H-indol-8-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-nitro-1H-indol-3-yl]-maleinimide:
(+)-2-(iH-indol-3--yl)-3-(1-(2-methoxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide:
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide:
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methylthio-1H-indol -3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methylthio-iH-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-2H-indol-~-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-8-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[5,7-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-[4-acetylamino-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamina-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(-)-~-[7-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[4-amino-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
~~r~~~, (-)-~-[5-amino-1-{2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-~-[6-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[6-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-iFt-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
(--)-2-[7-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-~-{1H-indol-3-yl)-maleinimide;
(-)-~-[4-bromo-1-(2-meth~xy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl~--maleinimide;
(-)-2-[5-bromo-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-andol-3-yl)-maleinimide;
(-)-2-[6-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-{2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(2-methoxy-3-dimethylami.nopropyl)-1H-indol-3-y1]-3-{1H-indal-3-yl)-maleinimide;
(-)~2-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(°)-2-[6-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-fluoro-1-(2-methoxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-fluoro-1-(~-methoxy-3~dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1°(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-hydraxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-hydroxy-1-(2-me~thoxy-3~dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-i.ndol-3~y1]-3-(1H-indo3.-3-yl)-maleinimide;
(-)-2-[4-trifluoromethyl-1-(2-methoxy~3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-methoxy- 3-dimethylaminoprapyl)-1H-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-~.H-indol-3-yl]-~-(1H-indol-~-yl)-maleinimide;
- 151 - ~ ebb ~ ~.~
(-)-2-[7-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[4-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-y1)-3-[5-methoxy-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3 -[6-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[7-methoxy-1-(a-methoxy-s-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5,&-methylendioxy-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide:
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-~-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-maleinimide:
(-)~2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methyl-2H-indol-~-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methyl-iH-indol-3-yl]-maleinimide;
(-)-2~(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-nitro-iH-indol-3-yl]-maleinimide;
1.52 - _~ a (-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-nitro-1H-indol-~-yl]-maleinimide;
(_)_2_(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-s-nitro-iH-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-nitro-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)--4-methylthio-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
(-)_2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminoprapyl)-iH-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol--3--yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[4 -acetylamino-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(2-dimethylaminoethyl)-1I~I-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-~.-(2-dimethylaminoethyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 153 - ~~c.~~~.~
2-[?-acetylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[5-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
2-[6-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[?-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-bromo-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-brama-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[?-bromo-1-(2~dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3 -y1)-maleinimide;
2-[5-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
2-[5-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[6-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoxomethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[5-trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7 -trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-~-[4-methoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-y1)-3-[6-methoacy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol~-3-yl)-3-[7-methoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-4,5-methylendioxy-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-5,6-methylendioacy-1H-indol-3-yl ] -maleinineide;
2-(1H-indol-3-yl)-3-[1-(Z-dimethylaminoethyl)-6,7-methylendio~cy-1H--indol-3-yl ] -maleinimide;
2-(1H-indol-3-yl)-3-[4-methyl-1-(2-dimethylaminoethyl)-~,H-indol-~-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-~.-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-;i-yl)-3-[6-methyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl)-maleinimide;
.2-(iH-indol-3-yl)-3-[1-(2-dimethylaminoethyl}-4-nitro-iH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[~.-(2-dimethylaminoethyl)-6-vitro-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[1-(2-dimethylaminoethyl)-7-vitro-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dime~hylaminoethyl}-4 -methylthio-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-5-methylthio-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[1-(2-dimethylaminoethyl)-6-methylthio-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3~yl}-3-[6,7-dimethoxy-1-(2-dimethylaminoethyl}-iH-indol-3-yl]-maleinimide;
2-[4-aaetylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
°
- 157 - ~~ e~.~~' 2-[5-acetylamino-1-(3-dimethylaminoprapyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-dimethylaminopropyl)~1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-amino-1-(3-dimethylaminopropyl)°1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-~.~(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinim$de;
2-[~-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~~bromo-1-(~-dimethylaminopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3~-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
a-[7-bromo-1-(3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4 -chloro-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
2-[5-chloro-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[6-ahloro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-dimethylaminopropyl}-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[6-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-hydroxy-1-(3-dimethylaminopropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide:
2-[5-h,ydroxy-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-hydroxy-1-(3-dimethylaminopropyl}-iH-indol-3-yl]-3-(1H-indol-3-yl)-malginimide:
2-[7-hydroxy-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-~-(1H-indol-3-y1)-maleinimide;
~~~~ t..
- 15 9 - .s. ei 2-[4-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[4-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-~-yl)-3-[7-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-y1)-maleinimide;
2-(1H-indol-3-yl)-~-[1-(3-dimethylaminopropyl)-4,5-methylendioxy-IH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-y1)-3-[1-(3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methyl-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~-(1H-indol-3-yl)-3-[6-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~ ,~ Y~ ~~ ~ ,-160 - ~~.'a'.e>a:l~i 2-(1H-indol-3-yl)-3-[7-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
s-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-4-nitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-y1)-3-[1-(3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-6-vitro-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-7-vitro-iH-indol-~-yl]-maleinimide;
2--(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-~-methylthio-IH-indol-3-yI]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
2-(iH-indoi-3-yl)-3-[1-(3-dimethylaminopropyl)-6-methylthio-iH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)~-3-[6,7-dirnethoxy-1-(3-dimethylaminopropyl)-1H-lndol-3-yl]-maleinimide;
2-[4-aaetylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~~ - 161 - ~°r ~ .~ e.~ ~:~
2-[5-acetylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-methylaminopropyl)-1H-indol -3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-amine-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(~-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
Z°[5-benzyloxy-1-(~-methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleini~ide;
2-[6-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-a-yl)-maleinirnide;
2-[5-bromo-1-(3-methylaminopropyl)-iH-indol-~-yl]-3-(1H-indol-3-yl)-male.inimide;
- 162 - _~e~
2-[6-bromo-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl) -maleinimide;
2-[5-chloro-1-(3-methylaminopropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-ahloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H~~indol-3-yl)-maleinimide;
2-[5-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
2-[7-fluoro-1-(3-methylaminopropyl)-1H-indol-~-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(~-methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-hydroxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
_, 2-[7-hydroxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[6-trifluoromethyl-1-(3-methylaminopropyl}-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[4-methoxy-1-(3-methylaminopropyl)-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl}-3-[5-methoxy-1-(~-methylaminopropyl)-1H-indol -3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[6-methoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl}-3-[1-(3-methylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indal-3-yl)-3-[1-(3-methylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[9~-methyl-1-(3-methylaminopropyl}-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-4-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-5-vitro-1H-indol-3-y1]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-6-vitro-1H-indol-3-yl]-.maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-7-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylarainopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-6-methylthio-1H-indol-3-y1]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-!-methylthio-1H-indol-3-yl]-maleinimide;
~-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
~-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
- 165 - ~.~s.~~~i~
2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-{3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[4-acetylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-{4-morpholino)propyl)~-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[7-aaetylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[4-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-~3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-(4-morplnolino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[5-benzyloxy-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-benzyloxy-1-(3-(4-morpholino)propyl)-~1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[7-benzyloxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[4-bromo-1-(3-(4-morpholino)propyl)-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[6-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-(4-morpholino)propyl)-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-(~-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
2-[7-chloro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-(4-morpholino)propyl)-IH-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
2-[5-fluoro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2 -[6-fluoro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-[7 -fluoro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
d :L 5:;7 d..: r 2-[5-hydroxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
a-[s-hydroxy-1-(a-(4-morpholino)propyl)-a.~a-indol-s-yl]-a-(iH-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-(4-~orpholino)propyl)-1H-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(iH-indol-3-yl)-3-[4-methoxy-1-(3-(4-morphalino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[6-methoxy-1-(3-(~-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methoxy-1-(3-(4°morpholino)propyl)-1Fi-indol-3-yl]-maleinimide;
2~(1H-indol-3-yl)-3-[4,5-methylendioxy~1-(3-(4-morpholino)prapyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[5,s-methylendioxy-1-(s-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide;
2-(iH-indal-3-yl)-3°[6,7-methylendioxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
' ~9' .d - ~ ~ ':.y~ ~ , ~-(1H-.indol-3-yl)-3-[4-methyl-1-(3-(&-morpholino)propyl)-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-inclol-3-yl)-3-[a-methyl-1-(3-(4-morpholino)propyl)-1H-indol-3-y1]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-4-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-6-vitro-2H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-7-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[6-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
z-(1H-indol-3-yl)-3-(4,5-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
.... 169 - ~~ii~~.~a~.s''~~..~
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indal-3-yl]-maleinimide;
2-[4-acetylamino-1-(3-(2-nitroguanidina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimidet 2-[5-acetylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep 2-[6-acetylamino-~.-(3-(2-nitroguanidino)prapyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-(2-nitroguanidino)propyl)-2.H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[6-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-(2-nitroguanidino)progyl)-1H-indol-3-~yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-benzyloxy-1-(3-(2~nitraguanidino)prapyl)-1H-indol-3~yl]-~-(1H-indol-3-yl)-maleinimide;
a ~:~_~~~~~a 2-[7-benzyloacy-1-(3-(2-nitroguanidino)propyl}-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[5-bromo-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[6-bromo-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-bromo-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[4-chloro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
2-[5-chloro-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[6-chloro-1-(3-(2-nitrcguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[7-chloro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[4-~luoro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
Z~[5-fluoro-1-(3-(2-nitroguanidino)propyl)-1H-indol~3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6~:~luoro-1-(3-(2-nitroguanidino)propyl}-iH-indol~3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[7-fluoro-1-(3-(2-nitroguanidino)prapyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[4-hydraxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-{iH-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[6-hydroxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(3-(2-nitroguanidino)gropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoramethyl-1-(3-(2-nitraguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-(2-nitroguanidino)prapyl)-iH-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-(2-nitroguanidino)prapyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-a-[4-methoxy-1-(3-(2-nitroguanidina)propyl)-iH-indol-3-yl]-maleinimide;
~-(1H-indal-3-yl)-3-[5-methoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3~yl)-3-[7-methaxy~1-(3-(2-nitroguanidino)prapyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-~-yl)-3-[4,5-methylendioxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
- 172 - ~:~.~~~)~J
2-(1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[6,7-methylendioxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methyl-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[5-methyl-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methyl-1-(3-(2--nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2'(1H-indol-3-yl)-3-[4-vitro-1-(3-(2°nitroguanidino)propyl}-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[5-vitro-1-(3-(2-nitroguanidino}propyl)-iH-indol-3-yl]-maleinimid~;
2-(1H-indol-3-yl)-3-[6-vitro-1-(3-(2-nitroguanidino}propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-vitro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[4-methylthio-1-(3-(2-nitroguanidino}propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-m~thylthio-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methylthio-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-~maleinimide;
2-(1H-indol-3-yl)-3-[7-methylthio-1-(3-(2-nitroguanidina)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[5,6-dimethoxy-I-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-(3-(2-nitroguanidino)progyl)-1H-indol-3-yl]-maleinimide;
2-[~-acetylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-(1.-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-I-(3-(1-piperidina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-ma~leinimide;
2-[4-amino-I-(3-(1-piperidino)propyl)-2H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-(1-pigeridino}propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
Z-[6-amino-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-(1-piperidino)propyl)-1H-indol~3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-lndol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-malei.nimide:
2-[6-benzyloxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-y-(3-(1-piperidino)propyl)-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(3-(1-piperidino)propyl)-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-bromo-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-~-(2H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
z-[5-ahloro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[4-;Fluoro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl?-3-(1H-indol-3-yl)-maleinimide;
2-[5-:~luoro-1-(3-(~.-piperidino)p.ropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-fluoro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydraxy-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-(1-piperidina)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[6-hydroxy-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-hydroxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~-trifluoromethyl-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(lH~indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[6-trifluoromethyl-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yI)-3-[4-methoxy-1-(3-(1-piperidino)propyl)-1H-indo:l-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidina)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[6-methoxy-1-(3-(2-piperidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-y1)-3-[h,5-methylendioacy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[6,7-methylendioxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimic'ie;
2-(1H-indol-3-yl)-3-[4-methyl-1-(3-(1-piperidino)propyl)-~iH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[5-methyl-1~(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-(1°piperidino}propyl)-1H-indol-3-yl]-maleinimidet 2-(iH-indol-3-yl)-3-[7-methyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[~-nitro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-nitro-1-(3-(1-piperidino)propyl)-1H-indol-~-yl]-maleinimide:
~-(1H-indol-3-yl)-3-[6-nitro-1-(3-(1-piperidina)propyl)-iH~
indol-3-yl]-maleinimide;
2-(1H-indal-3-yl}-3-[7-nitro-1-(3-(2-piperidino)propyl}-iH-indol-~-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methylthio-1-(3-(1-piperidino)prapyl}-1H-indol-3-yl]-maleinimide;
-1~~-2-(1H-indol-3-yl)-3-[5-methylthio-1-(3-(1-piperidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methylthio-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methylthio-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[6,Z-dimethoxy-1-(3-(1-piperidino)propyl)-iH-indol-3-yl]-maleinimide:
bis-2,3-(4-aoetylamino-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-acetylamino-1H-indol-3-yl)-maleinimide:
bis-2,3-(6-acetylamino-1H-indol-3-yl)-maleinimide:
bis-2,3-(7-acetylamino-iH-indol-3-yl)-maleinimide;
bis-2,3-(4-amino-1H-indol-3-y1)-maleinimide;
bis-~,3-(5-amino-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-amino-1H-indol-3-yl)-maleinimide:
bis-2,3-(7-amino-1H-indol-3-yl)-maleinimide:
bis-~,3-(4-benzyloxy-iH-indol-3-yl)-maleinimide:
bis-2,3-(6-benzyloxy-1H-indol-3-yl)-maleinimide;
bis-2,3-('7-benzyloxy-1H-indol-3-yl)-maleinimide;
-1?8-bis-2,3-(4-bromo-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-bromo-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-bromo-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-chloro-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-chloro-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-chloro-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-fluoro-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-fluoro-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-fluoro-1H-indol-3-y1)-maleinimide;
bis-2,3-(~-hydroxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(f>-hydroxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-hydroxy-1H-indol-3-y1)-maleinimide;
bis-2,3-(4-trifluoromethyl-1H-indol-3-yl)--maleinimide;
bas-2,3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-trifluoromethyl-iH-indol-3-yl)-maleinimide;
bis-2,3-(?-trifluoromethyl-iH-indol-3-yl)-maleinimide;
bis-2,3-(4-methoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-methoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(?~methoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(6,7-methylendioxy-1H-indol-3-yl)-maleinimide:
bis-2,3-(4-methyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-methyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(7-methyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-vitro-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-vitro-1H-indol-3-yl)-maleinimide;
bis-2,3-(~-vitro-IH-indol-3-yl)-maleinimide;
bis-2,3-(7-vitro-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-methylthio-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-methylthio-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-mathylthio-iH-indol-3-yl)-maleinimide;
bis-2,3-(7-methylthio-1H-indol-3-yl)-maleinimide;
bis-2,3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(6,7-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-ac~tylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)~5-amino-1H-indol-3-yl]-3-(5-amina-1H-indol-3-y1)-malei.nimide;
2-[1-(3-(amidinothio)propyl)-5-benzyloxy-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
~~~ .1EL P.P~
2-[1-(3-(amidinothio}propyl)-5-bromo-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-chloro-1H-indol-3-yl]-3-(5-chloro-3H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-~-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)prapyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-2H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4,5-methylendioxy-1H°indol-3-yl]--3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[2-(3-(amidinothio)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-malein:imide;
2-[1-(3-(amidinothio)propyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-methylthio-1H-indal-~-yl]-3-(5-methylthio-iH-indol-~-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-4,5-dimethoxy-1H-indol~3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-~(3-(amidinothio)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-~.H-indol-3--yl)-maleinimide;
.S
2-[5-acetylamino-1-(2-aminoethyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(2-aminoethyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-benzyloxy-iH-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-(1-(2-aminoethyl)-5-bromo-1H-indol-3-yl]-~-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-chloro-IH-indol-3-yl]-3-(5-chloro-1H-indol-3-yl}-maleinimide;
2-(1-(2-aminoethyl}-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl}-maleinimide;
2-[1-(2-aminaethyl)~5-hydroxy-1H-indol-~-yl]-3-(5-hydroxy-iH-indol-3-yl}-maleinimide;
2-[1-(2-aminoethyl}-5-trifluoromethyl-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl}-maleinimide;
~-[1-(2-aminoethyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl}-maleinimide;
2-(1-(2-aminoethyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yI)-maleinimide;
2-[1-(2-aminoethyl)-5,6-methylendioxy-iH-indol-3-yl]-~-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
2-[1-(2-aminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide:
2-[5-acetylamino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide:
2-[5-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-benzyloxy-1H-indol-3-yl]-3-(5-benzyloxy_ 1H-indal-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-5-bromo-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-5-chloro-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-fluoro-1H°indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-malainimide;
2-[1-(3-aminopropyl)-5-rnethoxy-1H-indol-3-yl]-3-(5-methaxy-1FI-indol-3-y1)-maleinimide;
2-[1-(3-aminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3~(~,5-methylendioxy-1H-indol-3-yl)-maleinimide;
~~~ ~~e 2-[1-(3-aminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl}-maleinimide;
2-[1-(3-aminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-vitro-iH-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methyithio-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
z-[~.-(3-aminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,s--dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(3-ethaxy-2-hydroxypropyl}-1H-indol-3~
yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(i)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-3.H-indol-3-yl)-maleinimide:
(~}-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-iH-indol-3-yl)-maleinimide:
(~)-2~[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-ohloro-1H-indol~3-yl)-maleinimide;
(t}~2-[1-(3-ethoxy-2-hydroxypropyl)-5~fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)~maleinimide;
(~)°2-[1-(3-ethoxy-2-hydroxypropyl)~5~hydroxy-1H~indol-3-yl]-3-(5-hydroxy-1H-indol~3-yl)-maleinimide;
(~j-2-[1-(3-ethoxy-~-hydraxypropyl)-5-trifluoromethyl-1H-indol-3-y1J-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxyprapyl)-5-methoxy-1H-indol-3-y1J-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(ø)-2-[I-(3-ethoxy-2-hydroxypropylj-4,5-methylendioxy-1H-indol-3-ylJ-8-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(~)-2-[7:-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-ylJ-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-ethoxy-2-hydroxypropylj-5-methyl-1H-indol-3-y1J-3-(5-methyl-1H-indol-3-yl)-maleinimidei (~j-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-ylJ-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indol-3-y1J-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-y1J-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(~j-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-aoetylamino-1-(3-ethoxy-2-hydroxypropylj-1H-indol-3-y1J-3-(5-acetylamino-1H-indol-3-yl)-maleinimide~
(+)-2-[5-amino-1-(3-ethoacy-2-hydraxypropyl)-1H-indal-3-y1J-3-(5-amina-1H-indol-3-ylj-maleinimide;
(+)-2-[5-benzyloxy-1-(3-ethoxy-2-hydroxypropylj-1H-indol-3-y1J-3-(5-benzyloxy-1H-indol-3-ylj-maleinimide:
(+)-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-y1J-3-(5-bromo-1H-indol-3-yl)-maleinimide;
~a ~.t~j~e>~.9~i~
- is5 -(+)-2-[5-chloro-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(+)-2-(1-(~-ethoxy-2-hydroxypropyl)-5-fluoro-1H-indal-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-hydroxy-iH-indol-3-yl]-3-(5-hydroxy-iH-indol-3-yl)-maleinimide;
(+}-2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yI]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxygropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(+}-2-[1-(3-ethoxy-2-hydroxyprapyl}-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(+)-2°[1-(3-ethoxy-2-hydroxypropyl)-5-methyl-iH-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl}-5-nitro-iH-indol-~-yl]-3-(5-nitro-1H-indol-3-yl}-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)~5,6-dimethoxy-1H-indol-3-y1]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
~'~~j.~~~~
(-)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(3-ethoxy-Z-hydroxypropyl)-1H-indol-3-y1]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-iH-indol-3-yl)-maleinimide;
(-)°2-[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro--1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(-)°2-[1-(3-ethoxy-~~hydroxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(-)'2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,G-methylendioxy-iH-indol-3-yl]-3-(5,ti-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1~(3-ethoxy-2-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3~
(5-methyl-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-y1]-3-(5-vitro-iH-indol-3-yl)-maleinimide;
(-)--2-[1-(3-ethoxy-2-hydroxyprapyl)-5-methylthio-1H-indal-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(-)_2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;-2-[5-amino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(2-diethylam~.noethyl)-1H-indol-3-yl]-~-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yI]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(2~-diethylaminoethyl)-iH~indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-fluoro-1H-indol-3-yl]-3~(5-fluoro-1H-indol-3-yI)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-hydroxy-1H-indol-3-yl]--3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yI)-maleinimide;
2-[Z-(2-diethylaminoethyl)-5-methoxy-~.H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-G1-(2-diethylaminoethyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
-. 188 -2-[1-(2-diethylaminoethyl)-5-methyl-1H-indal-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-methylthio-1H°indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethyiaminoethyl)-4,5-dimethoxy-1FT-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl}-maleinimide;
(~)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yI]-3-(5-acetylamino-iH-indol-3-yl}-maleinimide;
(~}-2-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl}-maleinimide;
(~}-2-[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(~)-2-[5-chloro-1-(3-diethylamino-2-hydroxypropyl}-2H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(t)-2-[1-(3-diethylamino-2-hydrox~propyl)-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(t}-2-[1-(3-diethylamino-2-hydroxypropyl}-5-hydroxy-1H-indol-~-yl]-3-(5-hydroxy-1H-indol-3-yl}-maleinimide;
(t}-2-[1-(3-diethylamino-2-hydroxypropyl}-5-trifluoromethyl-1H-indol-3-~yl]-3-(5-trifluoromethyl-~.H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxyprapyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendiaxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxyprapyl)-5-methyl-iH-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-nitro-iH-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthia-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(~~,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)°2-[1-(3-diethylamina-2-hydroxyprapyl)-5,6-dimethaxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol°3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-.(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-iH-indal-3=yl]-3-(5-benzyloxy-1H-~indol-3-y1)-maleinimide;
(+)-2-[5-broma-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-bromo-iH~-indol-3-yl)-maleinimide;
(+)-2-[5-chlora-1-(3-diethylamino-2-hydroxypropyl)-1H-~indol-3-yl]-3-~(5-chloro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamina-2-hydroxypropyl)-5-fluoro-iH-indol-3-yl]-3-(5-fluoro-iH-indol-3-y1)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-hydroxy-1H-i.ndol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-trifluoromethyl-iH-indol-3-yl]-3-(5-trifluoromethyl-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indnl-3-yl)-maleinimide;
(+)-2-[1,-(3-diethylamino-2-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-~-yl)-maleinimide;
(+)-~-[1-(3-diethylamino-2-hydroxypropyl)-5-vitro-2H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-z-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxyprrrpyl)-5,6--dimethoxy-iH-indal-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl)-maleinimide;
(-)-2-[5-aaetylamino-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-acetylamino-iH-indol-3-yl)-maleinimide;
(-)-~-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
- 191 - ~~ ~~~'iJ
(-)-2-[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-2H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-7l°(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(~-diethylamino-2-hydroxypropylj-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide:
(-j-2-[1-(3-diethylamino-z-hydroxypropyl)-5-hydroxy-2H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
(_)_~_[Z_(3_diethylamino-2-hydroxypropyl)-~k,5-methyiendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-~-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropylj-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleini.mide:
(-j-2-[1-(3~diethylamino-Z-hydroxypropyl)-5-methylthio-1'Ei-indol-~-yl]-3-(5-methylthio--1H-indol-3-yl)-maleinimide:
(-)~x-[1-(3-diethylamino-2-hydroxypropylj-4,5~dimethoxy-1H-3,ndol-3-yl]-3-(~,5-di.methoxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-{5-acetylamino-iH-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(5-chloro-1H-~indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-fluoro-iH-indol-3-yl]-3-(5-fluoro-iH-indol-3-ylj-maleinimide;
2-[1-(3-diethylaminopropyl)-5-hydroxy-iH-indol-3-yl]-3-(5-hydroxy-iH-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-die.thylaminopropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4,5-methylendioxy-1H-indal-3--yI]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[~,-(3-diethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-iH-indol-3-yl)-maleinimide;
2-[1-(~-diethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide:
~1 ~I ~ 'J
! ' 2-[1-(3-diethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4,5-dimethoxy-1H-indal-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indal-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-ethylaminoprapyl)-1H--indol-3-yl]-3-(5-acetylamino-1H-indoi-3-yl)-maleinimide;
2-[5-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-ethylaminopropyl)-1H-indbl-3-y1]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-ethylaminoprapyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimidep 2-jl-(3-ethylaminoprapyl)-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydraxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminoprapyl)-5-trifluaromethyl-1H-indal-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(A.,S-methylendiaxy-1H-indol-3-yl)-maleinimide:
- 19~ -2-[1-(3-ethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methyl-1H-indol-3-y1)-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-vitro-iH-indol-3-yl]-3-(5-vitro-1H--indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl}-5-methylthio-1H-indol-3-yl)-3-(5-methylthio-1H-indol-3-yl}-maleinimide;
2-[1-(3-ethylaminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl)-3~(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamina-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-amino-iH-indol-3-yl)-maleinimide;
(~)-2-(5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl)-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl}~-1H-indol-3-yl)-3-(5-bromo-1H-indol-3-yl}-maleinimide;
(t)-2-[5-chlora-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-y1)~~3-(5-chlora-1H-indol-3-yl}-maleinimide;
(t}-x-(5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(~)-2-(5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-~.-(2-hydroxy-3-dimethylaminoprapyl}-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(1-)-2-[1-(2-hydroxy-3-dimethylaminoprogyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl}-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl}-maleinimide;
(~)--2-[1-(2-hydroxy-3-dimethylaminapropyl)-5-nitro-iH-indol-3-yl]-3-(5-nitro-1H~indol-3-yl}-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5-methylthio-1H-indol-3-yl]-3~(5-methylthio-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(~}-2-[1-(2-hydroxy-3 -dimethylaminopropyl}-5,6-dimethoxy-1H-indol-3-yl]~3-(5,6~dimethoxy-1H-indol-3-yl)-maleinimid~;
(+}-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-~1H-indol-3-yl]-3-(5-acetylamino-1H-indol -3-yl}-maleinimide;
(+)-~2~[5-amino~1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol~3-yl]-3~-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide:
(+)-2-[5-bromo-1-(~-hydroxy-3-d3.methylaminopropyl)~1H-indol-3-yl]-3-(5-bromo-1H-indol-3-y1)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-y1)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl}-iH-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl}-maleinimide;
(+)-2-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(5-hydroxy-iH-indol-3-y1)-maleinim:ide;
(+)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yI)-maleinimide;
(+}-2-[1-(2-hydroxy-3-dimethylaminapropyl)-5-methoxy-1H--indol-3-yl]-3-(5-methoxy-iH-indol-3-yl}-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol--3-yl]-3-(4,5-methyl.endioxy-iH-indol-3-yl)-maleinimide;
(+}-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,~-methylendioxy-1H-indol-3-yl]-3~(5,6-methylendioxy-1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5-methyl-1H-indol-3-yl]-3-(5-methyl-iH-indol-3-y1)-maleinimide;
(+)~2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5-methylthio-iH-indol- 3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(+}-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(4,5-dimethoxy-1H-indol°~-y~.)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl}-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
- 197 - ~~G~~<.
(-)°~-[5-amino-1-(2-hydroxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydroxy-3-di'aethylaminopropyl)-iH-indol-3-yl]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(-)-2-[5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(-)-2-[5-hydraxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-y1]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-hydraxy-3-dimethylaminapropyl)-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxx-3-dimethylaminapropyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(-)~2-[1-(2-hydroxy~3-dimethylaminoprapyl)-5-vitro-1H-indol-~-yl]-3-(5-vitro-1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminoprapyl)-5-methylthio-1H-indol -3-yl]-3-(5-methyLthio-iH-indol-3-yl)-maleinimide;
- 198 - ~j_~ ~J~~.
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(°)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl)-maleinimide;
(~)-2-[5-aaetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-acetylamino-iH=indol-3-yl)°maleinimide;
(--1)-2-[5-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(5-amino-iH-indol-3-yl)-maleinimide:
(~)-2-[5-benzyloxy-1-(~-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide:
(t)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholina)propyl)-iH-indol-3-y1]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(ø)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(5-chloro-iH-indol-3-yl)-maleinimide:
(~)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)prapyl)-iH-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(~)-2-[5-hydroxy-1-(2-hydroxy-3-(4-morphalino)propyl)-1H-indol-3-yl]-3-(5-hydroxy-1H-indol°3-yl)-maleinimide:
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide:
(i)-2-[1-(2-hydroxy-3-(9-morpholino)propyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl)-maleinimide;
(f)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-~,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide:
- 199 - ~~.~~.~i~~~c.
(~)-2-[1-(~-hydroxy-3-(4-morpholino)propyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-vitro-,iH-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide;
(~)-2-[l.-(2-hydroxy-3-(4-morpholino)propyl)~-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide:
(+)-2-[5--acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(+)-~-[5-amino-1-(2 -hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morphoiino)propyl)~iH-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-(~-morpholino)propyl)-iH-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol--3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(+)-2-[5-fluora-~.-(2-hydroxy-3-(4-morpholino)propyl)~1H-indol-3-yl]~3-(5~fluoro-1H-indol -3-yl)-maleinimide;
(+)~2-[5-hydroxy-~.~(2-hydroxy-3-(4 -morpholino)propyl)-iH-indol-3-yl]-3°(5-hydroxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-~.-(2-hydroxy-3~(4-morphalino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-iH-indol-3-yl)-3-(5-methoxy-1H-indol-3-y1)-maleinimide;
(+)~2-[1-(2-hydroxy-3-(4-morpholino)propyl)-~,5-methylendioxy_ 1H-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide~
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)~-5,6-methylendioxy-1H-indol-3-yl)-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)~-5-methyl-iH-indol-3-yl]-a-(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-vitro-iH-indol-3-yI]-3°~(5-vitro-1H~-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio~1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholina)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)progyl)-5,6-dimethaxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2-hydroxy-3-(~1-morpholino)propyl)-iH-indol-3-yll-3-(5-amino-1H-indol-a-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol--3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-~.-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
'~ ~. ~) ~ ~ 't 7 (-)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl}-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-(4-morpholina)propyl)-1H-indol-3-yl]-~-(5-hydroxy-1H-indol-3-yl)-maleinim~.de~
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(~-morpholina)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl}-maleinimidet (-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(4-morpholino}propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indo~.-3-yl)-maleinimide:
(°)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(-)-~-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indal-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3_(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3~y1]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(1)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-amino-1H-indal-3-yl)-maleinimide;
C~'~~~~_ (~)-2-[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(~)°2-[5-bromo-l-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(1-)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimid~e;
(-~)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H--indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-{2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidina)propyl)-5,6-methylendioxy-1H-indol-3-y1]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methyl-~.H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(~,-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimid~;
(t)-~-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(2-piperidino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-a-(4,5-dlmethoxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydraxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-y1]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino}propyl}-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl}-maleinimide;
(+}-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-2-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-y1)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-(Z-piperidino}propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl}-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]d3-(5-hydroxy-1H-indol-3-yl}-maleinimide:
(+)-2-[5-trifluaromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H--indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(+)-2 -[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-2H-indal-3-yl]-3-(4,5-methylendioxy-1FI-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methyl,-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-nitro-2H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(I-piperidino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,f-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-2H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-~benzyloxy-z-{2-hydroxy-3-(1-piperidino)propyl)-2H-indol-3-yl]-3-(5-benzyloxy-1H-indol~3-yl)-maleinimide;
(-)-2-[5-bromo-1°(~-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(-)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-(1-pipmridino)propyl)-1H-~indol-3-yl]-3-{5-hydroxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1~(2-hydroxy-~-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-malsinimide;
(-)-2-(~.-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H-indol-~-yl]-3-(5-methoxy-1H-indol-3-yl)-male].nimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methoxy-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piper.idino)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-7.H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)~-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleini~nide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-7.H-indol-3-yl)-maleinimide;
(°)-2-[1-(2-hydroxy-3-(~.-piperidino)propyl)-~,5-dimethoxy-1H-indol-3-yl]-3-(~4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(-)-2-[2-(2-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-l.H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-5-acetylarnino-1H-~indol-3-yl)-maleinim~.de:
(~)-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(2,3~dihydroxypropyl)~1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(t)-2-[5-bromo-~,-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-~.H-indol-3-yl)-malein3mide;
(t)-2-[5-chloro-1-(2,3-dihydroxypropyl)-2H-indol-3-yl]-3-(5-chlaro-1H-indol-3-yl)-maleinimide:
~~.~e~~J~
(~)-2-(5-fluoro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(~)-2-[5-hydroxy-I-(2,3-dihydroxygropyl)-iH-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-2-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(ø)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(~)-~-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-lI3-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-~,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yI)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-vitro-iH-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
(t)-2-[2-(2,3-dihydroxypropyl)-5,6-dimethoxy-iH-indal-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-~-[5-aaetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-aoetylamino-iH-indol-3-yl)-maleinimide;
(~-)-2-[5-amino-1-(2,3-dihydroxypropyl)-JlH-indol-3-yl]-3-(5-amino-iH-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2,3-dihydroxypropyl}-iH-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-fluoro-ZFi-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl}-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(~,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5,6-methylendioxy-iH-indol-3-yl]-3°(5,6-methylendioxy-lI~-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3--(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-2-Z1-(2,3-dihydroxypropyl}-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H°-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide:
(+)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
.9 . a y E~
(+)-2-[1-(2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-y1]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2,3-dihydroxy~aropyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2,3-dihydroxypropyl)-3.H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3~(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[g_chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-hydroxy-iH-indol-3-yl)-maleinimide~
(-)-2-[5-trifluoromethyl-~.-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-IH-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide~
(-)-2-[~.-(2,3-dihydroxyprapyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
a ~ ~ ~t~ vrn ',,~ ~:3 ,~J e~!
(-)-2-[1-(2,3-dihydroxypropyl)-5-nitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthia-1H-indol~3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxyprapyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-hydroxypropyl)-1H-inclol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-amine-1H-indol-3-yl)-maleinimide:
2-[5-benzyloxy-1-(3-hydraxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-broma-1H-indol-3-y1)-maleinimide;
2-[5-chloro-1-(3-hydroxypropyl)-1H-indal-3-yl]-3-(5-chlaro-1H-indal-3-yl)-maleinimide;
2-[5-fluoro-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
2-[5-hydraxy-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-hydroxy-1H-indal-3-yl)-maleinimide;
2-[5-trifluaromethyl-1-(3-hydroxypropyl)-5-trifluoramethyl-1H-indol-3-yl]-3-(5-trifluoramethyl-1H-indal-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-methaxy-1H-indol-3-yl]-3-(5-methaxy-1H-indol-3-yl)-maleinimide;
- zzo -z-[1-(3-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5,6-~nethylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide~
2-[1-(3-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-y1)-maleinimide;
2-[1-(3-hydroxypropyl)-5-vitro-1H-indol-3-y:l]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-methylthio-1H-indo:l.-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl}-4,5-dimethoxy-1H-indol-3-yl]-3-(~,5_ dimethoxy-2H-indol-3-yl)-maleinimidet 2-[1-(3-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl}-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
Z-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3 isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-chloro-1H-indol-3-y1)-3-[5-chloro-1-(;~-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide:
2-(5-~luoro-~.H-indol-3-yl)-3-[5-fluoro-1.-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
~
""t«~ n ~?~ .~~~'xJ
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide~
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
2-[1-(3-isothiocyanatopropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimidet 2-[1-(3-isothiocyanatopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide:
2-[1-(3-isothiocyanatopropyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide:
2-[1-(3-isothiocyanatopropyl)-4,5-dimethoxy-1H-indol-3-yl)-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-(5-acetylamino-1H-indol-~-yl)-3-[5-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(t)-2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(2-methoxy-3-d~,methylaminopropyl)-1H-indol-~-yl]-male~.nimide;
(t)-~-(5-benzyloxy-1H-indol-3-yl)-3~[5-benzyloxy-1-(2~methoxy-3-dimethylarninopropyl)-1H-indol-3-yl]-maleinimide:
- 2~2 -(~)-2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-~.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(5-chloro-~.H-indol-3-yl)-~-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~j-2-(5-fluoro-2H-indol-3-yl)-3-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-2H-indol-3-yl]-maleinimide;
(~)-2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~j-2-(5-trifluoromethyl-1H-indol-3-y1)-3-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yI]-maleinimide;
(~)-2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-~.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-[1--(2-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H°indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-ylj-maleinimide;
(~j-2-[1-(2-methoxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-~-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(z-methoxy-3-dimethylaminopropyl)-5-nitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1.H-indol-3-yl)-maleinimide;
(~)-2-(4,5-dimethoxy-1H-indol-3-yl)-~3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-11H-indol-3-yl]-maleinimide;
(t)-2-(5,6-dimethaxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminapropyl)-1H-indnl-3-yl]-maleinimide;
(+)-2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-maleinimide;
(+)-2-(5-amino-1H-indol.-3-yl)-3-[5-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(5-benzyloxy-1H-indol-3-y1)-3-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol.-3-yl]-malei.nimide;
(+}-2-(5-bromo-1H-indol-3-yl}-3°[5-bromo-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-maleinimide;
(+)-2-(5-ahloro-1H-indol-3-yl)-3-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(5-fluoro-1H-inclol-3-yl)-3-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(5-hydroxy-1H-indol-3-yl}-3-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+}-2-(5-trifluoromethyl-1H-indol-3-yl)-~-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-maleinimide;
(+)-~-(5-methoxy--1H-indol-3-yl)-3-[5-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylaminopropyl)-4,5-methylendaoxy~
1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylaminopropyl}-5,6-methylend:ioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylamiisopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-~-[1-(2-methoxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-iH-indol-3-yl)-~-(5-methylthio-1H-indol-3-yl)-malsinimide;
(+)-2-(4,5-dimethoxy-1H-indol-3-yl}-3-[4,5-dimethoxy-1-(z-methoxy-3-dimethylaminopropyl}-1H-indol-3-ylJ-maleinimide;
(+)°2-(5,6-dime~thoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2 -methoxy-3-dimethylaminopropyl)-iH-indol-3-ylJ-maleinimide;
(-}-2-(5-acetylamino-iH-indol-3-yl}-3-[5-acetylamino-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-}-z-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1J-maleinimide;
(-)-2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-1-(z-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl)-maleinimide;
(-)-2-(5-chloro-iH-indol-3-yl)-3-[5-chlaro-1-(2-methoxy-3-dimethylaminopropyl}-iH-indol-3-ylJ-maleinimide;
(~)-2-(5-fluoro-1H-indol-3~-yl)-3-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
(-)-2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(z-methoxy-3-dimethylaminopropyl}-iH-indol-3-yIJ-maleinimide;
(-)-2-(5-trifluoromethyl-iH-indol-3-y1)-3-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-ylJ-maloini,mide;
(-}--z-[1-(z-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy_ 1H-indal-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
t;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5,c-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-~-(5-methyl-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-m~thylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-y1)-maleinimide;
(-)-2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(5,6-dimethoxy-1H-indol-3-yl)-~-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide:
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide:
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide:
2-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-~-yl)-3-[5-bromo-1-(2-dimethylaminoethyl)-1H-indol-3-yl)-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-[5-chlora-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(2 -dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
a a. ~
2-(5-tri~luoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-maleinimide;
2-[1-(2-dimethylaminoethyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-dimethylaminoethyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-[1-(2-dimethylaminoethyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-iH-indol-3-yl)-maleinimide;
2-[1-(2-dimethylaminoethyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide;
2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethaxy-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-maleinimide;
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-acetylamino-iH-indol-3-yl)-3-[5-acetylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~-(5-amino-iH-indol-3-yl)-3-[5-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-malein~.mide;
2-(5-benzyloxy-1H-indol-3-yl)-3-(5-benzyloxy-1-(3-dirnethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-~-yl)-3-[5-bromo-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~a ~ ~i 2-(5-chloro-1H-indol-3-yl)-3-[5-chloro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(~-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl--1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-iH-indol-3-yl)-3-[5-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-ylJ-maleinimide;
2-[1-(3-dimethylaminopropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
2-[1-(3-dimethylaminopropyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-(4,5-dimsthoxy-1H-indol-3-yl)-3-[4,8-dimethoxy-1-(3-dimethylaminopropyl)-iH-indol-3-y1]-maleinimide;
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(5-aoetylamino-iH-indol-3-yl)-~-[5-acetylamino~1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
~~~~.~~..~~~
2-(5-amino-1H-indol-3-yl}-3-[5-amino-1-(3-methylaminopropyl}-1H-indol-3-yl]-maleinimide;
2-(5-henzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-1-(3-methylaminopropyl}-1H-indol-3-yl]-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-[5-chloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3--methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-methylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-methylaminapropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-methylaminopropyl)-5-vitro-1H-indal-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-methylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
- zis -2-(4,5-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide:
2-(5,6-dimethoxy-iH-indol-3-yl}-3-[5,6-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-~-[5-acetylamino-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-3-yl}-3-[5-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-chloro-iH-indol-3-yl)-3-[5-chloro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide;
2-(5-hydroxy-iH-indol-3-yl)-3-[5-hydroxy-1-(3-(4-morvholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide:
Z-(4,5-methylendioxy-1H-indol-3-yl)-3-[4,5-methylendioxy-1-(3-(~t-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-methylendioxy-1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-(4-morpholinojpropyl)-iH-indol-3-yl]-maleinimide:
2-[1-(3-(4-morpholino)propyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-(5-methylthio-iH-indol-3-yl)-3-[5-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(4,5-dimethoxy-iH-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(~-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-ben~yloxy-iH-indol-3-yl)-3-[5-benzyloxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide:
2-(5-bromo-iH-indol-3-yl)-s-[5-bromo-1-(s-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-[5-chloro-1-(3-(2-nitroc~uuanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-y1)-3-[5-fluoro-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2~(5-hydroxy-1.H-indol-3-yl)-3-[5-hydroxy-1-(3-(~-nitracxuanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(5-trifluoromsthyl-iH-indol-3-yl)-3-[5-trifluoromethyl-1-(3-(~-nitroguanidino)prapyl)-1T~I-indol-3-yl]-malsinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
l'~,~1 ~ ~~~~:~
2-(4,5-methylendioxy-1H-indol-3-yl)-3-[4,5-methylendioxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-methylendioxy-1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(2-nitroguanidino)propyl)-1H-indal-3-yl]-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-vitro-1H-indol-3-yl)-3-[5-vitro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methylthio-1H-indol-3-yl)-3-[5-methylthio-1-(3-(2-nitroguanidino)propyl)-1H-indal-3-yl]-maleinimide;
2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(2-nitroguanidino)propyl)-1H-indoi-3-yl]-maleinimide;
2--(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3-(~.-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-iH-indol-3-yl)-3-[5-bramo-1-(3-(1-piperidino)prapyl)-1H-indol-3-yl]-maleinimide;
2-(5-~chlara-1H-indol-3-yl)-3-[5-chlora-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-floats-1H-indol-3-yl)-3-[5-floors-1-(3-(1-p3peridino)propyl)-1H-indol-3-yl]-maleinimide;
? .~ y; r,~1 r5, '3 ~~ ~ ~~ ~' x.~ ..~
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(4,5-methylendioxy-1H-indol-3-yl)-3-[4,5-methylendioxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-methylendioxy-1H-indal-3-yl)-3-[5,6-methylendioxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-(I-piperidino)progyl)-1H-indol-3-yl]-maleinimide;
2-(5-vitro-1H-indol-3-yl)-3-[5-vitro-1-(3-(1-piperidino)propyl)-1H-indoi-3-yl]-maleinimide;
2-(5-methylthio-1H-indol-3-yl)-3-[5-methylthio-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(1~-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-(amidinvthio)prapyl)-~t-dimethylamino-1H-indol-3-yl]-3--(~,H-indal-3-yl)-maleinimide;
2-[2-(3-(amidinathio)propyl)-5-dimethylamino-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-dimes,hylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 223 - G',a~.y~=~~~.'~
2-[1-(3-(amidinothio)propyl)-7-dimeth.ylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H°
indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-dimethylamino-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
2-[Z-(3-aminopropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(3-ethoxy-2-hydroxypropyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
Z-[1-(3-ethoxy-2-hydroxypropyl)~5~dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[1~(3-ethoxy-2-hydroxypropyl)-6~dimethylamino-1H-indol-3-yl]-3-(1H~indol-3-yl)-maleinimide;
2~[1-(3-ethoxy-2-hydroxypropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~_~'~:' 2-[1-(2-diethylaminoethyl)-4-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-6-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-dimethylamino-1H-indol-3-yl]-3-(iFi-indol-3-yl)-maleinimide;
(ø) 2-[1-(3-diethylamino-2-hydroxypropyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(3-diethylam.ino-2-hydroxypropyl)-5-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(3-diethylamino-2-hydroxypropyl)-6~dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~~) 2-[1-(3-diethylamino-2-hydroxypropyl)-7-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4~-dimethylamino-1H-indol-3-yl]-3-(1H-inddl-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
~[1-(3-ethylaminopropyl)-6-dimethylamino-iH-indol-3~-yl]~3-(iH-indol-3-yl)-maleinimide;
2-[1,-(3-ethylaminopropyl)-7-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(i) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-dimethylamino-1H-indol-3-yl]-3-(lEi-indol-3-yl)-maleinimide;
(~) 2-[~.-(2-hydroxy-3-dimethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)~maleinimide;
(~) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-dimethylamino-IH-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-dimethy~.amino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-hydxoxy-3-(1-piperidino)propyl)-5-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2,3-dihydroxypropyl)-4-dimethylamina-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimid~;
(t) 2-[1-(2,3-dihydroxypropyl)-5-dimethylamino-iH-indol-3-yl]--3-(1H-indol-3-yl)-maleinimide;
fa (~) 2-[1-(2,3-dihydroxypropyl)-6-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2,3-dihydroxypropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep 2-[1-(3-hydroxypropyl)-4-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-dimethylamino-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4-dimethylamino-iH-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-dimethylamino-1H-indol-3-yl]-maleinimide:
2-(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-6-dimethylamino-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-7-dimethylamino-1H-indol-3-yl]-maleinimidet (t) Z-(1H-indol-3-y7.)-3-[1-(2-methoxy-3-dimethylaminopropyl)-A-dimathylamino-iH-indol-3-yl]-maleinimide;
(i) 2-(iH-indol-3-yl)-3-[1-(2-metho~ty-3-dimethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-mal~inimide;
(~) Z~(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-dimethylamino-1H-indol-3-yl]-maleinimide;
(~) 2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-dimethylamino-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(IH-indol-3-yl)-3-[7-dimethylamino-1-(2-dimethylaminoethyl)-IH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[~-dimethylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-dimethylamino-Z-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-I-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-dimethylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-~-[4-dimethylamino-1-(3-methylaminopropyl)-1H-indol-3-yi]-maleinimide;
2-(1H-indol-3-yl)~3-[5-dimethylamino-1-(3-methylaminopropyl)~
1H-indol-3-yl]-maleinimide;
2-(7.H-indol-3-yl)-3-[G-dimethylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-~-[7-dimethylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-dimethylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-dimethylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[?-dimethylamino-1-(s-(~-morphoiino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-dimethylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
z-(1H-indol-s-yl)-3-[5-aimethylamino-z-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-1-(3-(2-nitroguanidina)propyi)-ZH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[?-dimethylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
a-(~H-indol-3-yl)-3-[4-dimethylamino-1-(3-(i-piperidino)propyl)-1H-indol-~-yl]-maleinimide;
2-(1H-indol-3-yl)-~-[5-dimethylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
Z-(1H-indol-3-yl)-3-[6-dimethylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-~-yl)-3-[?-dimethylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(a-(amid.nothio)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
_.. ~:i~ ~ ' 2-[1-(2-aminoethyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
(~) 2-[1-(3-ethoxy-2-hydroxypropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
(~) 2-[1-(3-diethylamino-2-hydroxypropyl)-5--dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2,3-dihydroxypropyl)-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamina-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-dimethylamina-iH-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide;
(t) 2-[1-(2-Methoxy-3-dimethylaminopropyl)~-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
_.
- ~so -2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-y1J-maleinimidet 2-{5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylaminn-1-{3-methylaminopropyl)-1H-indol-3-y1J-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-I-(3-(~-morpholino)propyl)-1H-indal-3-yl]-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-{3-(1--piperidinu)propyl)-1H-indol-3-yl]-maleinimide.
3S.) (~)-2-[1.-(3-Ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, dark red crystals, 130-134°C
prepared by process B by use of the BoC protecting group and epibromohydrin as alkylating agent;
39.) (~)-2-[1-(2-hydroxy-3-(~.-piperidino)-propyl)-1~i-indol-3-yl]-3-(1H-indol-3-yl)-malainimide, dark red crystals, 142°C, decomp., prepared by process B by use of the Bnc protecting group and epibromohydrin as alkylatirig agent;
4a.) (t)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide and 41.) (~)-2-[1-(3-diethylamirio-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide, as regioisomeric mixture 4:1, dark red crystals, above 150°C decomp., prepared by process B by use of the BOC protecting group and 1,1-diethyl-3-hydroxyazetidinium-chloride as alkylating agent;
42.) 2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide, 257°258°C, and with 43.) 2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide, as regioisomeric mixture 1:1, orange crystals, 150°C, prepared by pz~ocess B by use of the BOC protecting group:
44.) 2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-maleinimide, pale red crystals, 165-166°C, prepared by process A;
45.) 2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide and 46.) 2-[1-(3-diethylaminopropyl)-1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide, as regioisomeric mixture 3:2, pale red crystals, 206-208°C, decomp, prepared by process B by use of the BOC protecting group;
47.) 2-[1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide and 48.) 2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, as regioisomeric mixture 3:1, pale red crystals, 285-190'C, prepared by process B.
49.) 2-[~.-(3-diethylaminapropyl)-5-methoxy-1H-indol-3-yl]-3-(6-methoxy-1FI-indol-3-yl)-maleinimide and 50.) 2-[1-(3-diethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide, as regioisomeric mixture 5:1, red crystals, 176-182'C, prepared by process B.
-51.) 2-[5-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide and 52.) 2-(5-floor-iH-indol-3-yl)-3-[1-{3-dimethylaminoplopyl)-iH-indol-3-yl]-maleinimide, as regioisomeric mixture 3:1, 230-235°C.
Tn analogous manner the following compounds are prepared according to their substituents by one of the disclosed processes:
2-[1-(3-(amidinothio)propyl)-1H-indol-3-yl]~-3-{iH-indol-3-yl)-maleinimide;
2-[1-{2-aminoethyl)-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-[1-{3-aminopropyl)-iH-indol~3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
{-~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminoprapyl)-1H-indol-3-yl]-3-(iFI-indol-3-yl)-maleinimide;
(~)-2-[1-[2-hydroxy-3-(4-morpholino)prapyl]-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)_2-[1-.[2-hydroxy-3-(~-morpholino)propyl]-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
_ 29 -(-)-2-[1-[2-hydroxy-3-(4-morpholino)propyl]-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
2-(1H-indol-3-y1)-3-[1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(2H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylami.nopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-[3-(2-nitroguanidino)propyl]-1H-indol-3-yl]-maleinimide;
2-(4-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(6-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(7-acetylamino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(4-amino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(C-amino-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(7-amino-1H-indol-3-yl}-3-(1H-indol-3-yl)-maleinimide; .
2-(4-benzyloxy-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(5-benzyloxy-1H-indol-3-yl}-3-(iH-indol-3-yl)-maleinimide;
2-(s-benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(7-benzyloxy-1H-indol-3-yl}-3-(1H-indol-3-yl)-maleinimide;
2-(4-bromo-1H-indol-3-yl)-3-(iH-indol-3-yl}~-maleinimide;
2-(5-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2_(6_bromo-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(7-bromo-iH-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(4-chloro-iH-indol-3-yl)-3-(iH-indol-3-yl}-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(6-chloro-1H-indal-3-yl}-3-(iH-indol-3-yl)-maleinimide;
2-(7-chloro-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(4-fluoro-1H-indol-3-yl}-3-(1H-indol-3-yl)-maleinimide;
2-(5-fluoro-iH-indol-3-yl}-3-(iH-indol-3-yl)-maleinimide;
2-(6-fluoro-iH-indol-3-yl)-3-(1H-indol-3-yl}-malainimide;
2-(7-fluoro-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-(4-hydroxy-1H-indol-3-yl)-3-(iH-indal-3-yl)-maleinimide;
2-(5-hydroxy-1H-indol-3-yl}-3-(iH-indol-3-yl}-maleinimide;
2-(6-hydroxy-1H-indol-3-yl}~-3-(1H-indol-3-yl)-maleinimide;
2-(7-hydroxy-1H-indoi-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(4-trifluoromethyl-1H-indol-3-yl)-~-(1H-indol-3-yl)-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
a-(6-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-~-yl)-malelnlmlde;
2-(7-trifluoromethyl-1H-indol-3~y1)-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(4-methaxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(7-methoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indoi-3-yl)-s-(~,5-methylendioxy-1H-indol-3-y1)-maleinimide;
2-(1.H-indol-3-yl)-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6,7-methylendioxy-1H~indol-3-yl)-maleinimide;
2-(1H-~.ndol-3-yl)-3-(4-methyl-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6-methyl-1H-indol-3-yl)-maleinimide;
2-(1~I-indol-3-yl)-3-(7-methyl-1H-indol-3-yl)-maleinimide;
2-(iH-indol-3-yl)-3-(4-nitro-1H-indol-3-yl)-maleinimide;
~3~.-2-(1H-indol-3-yl)-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6-vitro-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(7-vitro-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(4-methylthio-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(5-methylthio-1H-indol-3-yl)-maleinimide:
2-(1H-indol-3-yl)-3-(6-methylthio-1H-indol-~3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(7-methylthio-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(~,5-dimethoxy-1H-indol-~--yl)-maleinimide;
2-(1H~-indol-3-yl)-3-(5,~-dimethoxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-(6,7-dimethoxy-1H-indol-3-yl)-maleinimide;
2-(4-acetylamino-1.-(3-(amidinothio)propyl)-1H-indol-:~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
~°[6-aGetylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(1H--indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-amino-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-amino--1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-amino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-7-amino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-5-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-benzyloxy-1H-indol-3-y1,]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-7-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
2-[1-(3-(amidinothia)propyl)-4-bromo-1H-indol-3-yl]-3-(1H°-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-5-bromo-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-6-bromo-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-7-bromo-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-6-chloro-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio)propyl)-7-chloro-1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-{3-(amidinothio)propyl)-4-fluaro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-{3-(amidinothio)propyl)-4-hydroxy-iH-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-hydroxy-1H-indol-3-ylJ-3-{1H-indol-3-yI)-maleinimide;
2-[1-{3-(amidinothio)propyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-trifluoromethyl-2H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-trifl~oromethyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidino~hio)propyl)-?-trifluoramethyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-methoxy-~iH~indol~3-ylJ-3-(iH-indol-3-yl)-maleinimide;
- 35 - ~~~~t3 2-[1-(3-(amidinothio)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-s-methoxy-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1-(3-(amidinothio)propyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4,5-methylendioxy-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)~5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6,7-methylendioxy-1H-indol-3-yT]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4-methyl-1H-indol-3-yl]-3-(:LH-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-methyl-7.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1-(3-(amidinothio)propyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)prapyl)-7-methyl-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
z-~~.--(s-(amiainothio)propyl)-a-vitro-~.H-indol-s-yl]-s-(iH-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol -3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-vitro-2H-indol-3-yl]-3-(1H-indnl-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-7-vitro-iH-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[1-(3-(amidinothio}propyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio}propyl)-5-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio}propyl}-6-methylthio-1;H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(3-(amidinothio}propyl}-4,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-(amidinothio}propyl}-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(3-(amidinothio)propyl}-6,7-dimethoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-acetylamino-1-(2-aminoethyl)-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
2-[5-acetylamino-Z'(2-aminoethyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-aaetylamino-1-(2-aminoethyl)-iH-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[7-acetylamino-1-(2-aminaethyl}-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4- amino-1-(2-aminoethyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
_3~-2-[5-amino-~,-(2-aminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(2-aminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(2-aminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[~.-(2-aminoethyl)-4-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(~-aminoethyl)-5-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(2-aminoethyl)-6-benzyloxy-aH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
~-[1-(2-aminoethyl)-'7-benzyloxy-1H-indol-3-y1]-3-(~.H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-~-bromo-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(2-aminoethyl)-5-bromo-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-bromo-1H-indol~3-yl]-3-(1H-indol-3-yl)-maleinimide;
x-[1-(2-aminoethyl)-7-bromo-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimid~;
2-[1-(2~aminoethyl)-4-chloro-1F~-indol-3-yl]-~-(1H-indol-3-yl)~
maleinimide;
2-[1-(2-aminoethyl)-5-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-~8-z-[1-(z-aminoethyl)-6-chloro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-7-chloro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-4-fluoro-1H-indol-~-yl]-~-(iH-indol-3-yI}-maleinimide;
2-[1-(z°aminoethyl)-5-fluoro-1H-indol-3-yl]~-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-~-yl}-maleinimide;
2-[1-(2-aminoethyl)-7-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[1-(z-aminoethyl)-4-hydroxy-iH-indol-3-yl]-3-(1H-indol--3-yl}-maleinimide;
2-[1-(z-aminoethyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-6-hydroxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-7-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(z-aminoethyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-trifluoromethyl-1~I-indol-3-yl]-a-(iH-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-trifluoromethyl-iH-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
°
2-[1-(2-aminoethyl)-7-tri~luoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-~-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol~3-yl)--maleinimidet 2-[1-(2-aminoethyl)-6-methoxy-1H-indol-3-yl;j-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl.)-4,5-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[1-(2-aminoethyl)-4-methyl~iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1~(2~aminoethyl)-6-methyl-1H-indol~3-yl]~3-(iH-indol-3-yl)~
maleinimide;
2-[1~(2~aminoethyl)-7-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4-vitro-1H-indol~3-yl]~3~(1H~indol-3~yl)-maleinimide:
-2-[1-(2-aminoethyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(~-aminoethyl)-7-vitro-iH-indol-3-yl]--3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~.-(2-aminoethyl)-5-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[1-(2-aminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[1-(~-aminoethyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~1-acetylamino-1-(3-aminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5wacetylamino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-aminopropyl)~1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
--~. ~~~.~~r~
2-[?-ace~ylamino-1-(3-aminopropyl)-iH-indol-3-yl]-3-(iH-indal-3-ylj-maleinimide;
2-[4-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)°
maleinimide;
2-[6-amino-1-(3-aminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
2-[1-(3-aminopropyl)-4-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-benzyloxy-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-6-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yIj-maleinimide:
2-[1-(~-aminopropyl)-7-benzyloxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(3-aminopropyl)-4-bromo-1H-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-bromo-iH-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[1-(a-aminopropyl)-6-bromo-1H-indal-3-yl]-3~(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-7-bromo-iH-indol-3-yl]-3-(1H-indal-~-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-chloro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-chloro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-chloro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-7-chloro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-fluoro-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-fluoro-iH-indol-3-yl]-3-(1H-indol-~3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-fluoro-1H-indol-3-yl]-3-(iH-indol-~-y1)-maleinimide;
2-[1-(3-aminopropyl)-7-fluoro-1H-indal-3-yl]°~-(1H-indol-~-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-hydroxy-1H-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(~-aminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-hydroxy-iH-indol-3-yl]-3-(1H-indo:!-3-yl)-maleinimide;
Z-[1-(3-aminopropyl)-7-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-trifluoromethyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-rnaleinimide:
-~3-2-(1-(3-aminopropyl)-5-tri~luoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~.-(3-aminopropyl)-7-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yI)-maleinimide;
2-[~.~(3-aminopropyl}-5-methoxy-1H-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
2-[1-(3-aminopropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-7-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(1-(3-aminopropyl}-~,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[1-(3-aminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl}-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
~-[1-(3-aminoprapyl)-4-methyl-iH-indol-3~yl]-3-(iH-indol-3-yl)-maleinimide 2-[1-(3-aminopropyl)-5-methyl-iH-indol-3-yl]-3-(iH-indol--3-yl)-maleinimide;
2-(1-(3-aminoprapyl)-6-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-~4-2-[1~-(3-aminopropyl)-7-methyl-1H-indol-3-ylJ-3-(1H-indol-°3-yl)-maieinimide;
2-[1-(3-aminopropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminoprapyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-9~-methylthio-1.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(3-aminopropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl ) -maleini~nide ;
2-[1-(3-aminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5,~°dimethoxy-1H-indol~3-yl]-3-(1H~indol--3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(*)-2-[4-acetylamino-1-(3-ethoxy-2-hydroxyprapyl)-1H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)_~_[s-aGe~tylamino-~.-(~-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
(~)-2-[7-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-ma~leinimide:
(~)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(1-)-2-[6-amino-1-(3-ethoxy-2-hydroxypropyl)-li-I-indol-3°yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-amino-I-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[4-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]_ 3-(1H-indol-3-y1)-maleinimide;
(t)-2-[5-benzyloxy-1-(3-ethoxy-2-hydrdxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[6-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleini~mide;
(°1)-2-[7 -benzyloxy-1-(3-ethoxy-~-hydraxypropyl)-1H-indol-3-yl]-3-(1~EI-indol-3-yl)-maleinim3de:
(t)-2-[4-bromo-1-(3-ethoxy~2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(t)-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
-~6-(~)-2-[6-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-bromo-1-(3-ethoxy-Z-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(1-)-z-[~-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[6-chloro-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yI]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-fluaro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-ethoxy-2-hydraxypropyl)-6-fluaro-1H-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-fluoro-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydr~oxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(1Fi-indol-~-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~}-2-[1-(3-ethoxy-~-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl}-5-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(,1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methoxy-1H-indol-~-yl]-3-(1H-indol-3-y1)-maleinimide;
(-~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(1-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~}-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-z-[1-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy-1.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinim~,de;
(t)-2-[1-(3-ethoxy-2-hydroxypropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methyl-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methyl-IH-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methyl-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methyl-IH-indol-3-yl]°-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-vitro-IH-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(-~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(~)-2-[I-(3-ethoxy-2-hydroxypropyl)-s-vitro-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[1-(3-ethoxy-2-hydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[I-(3-ethoxy-2-hydroxyprogyl)-4-methylthio-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[I-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleini~ide;
(~)-2-[I-(3-ethoxy-2-hydroxypropyl)-6-methylthio-IH-indol-3-yl]-~-(IH-indol-3-yl)-maleinimide;
(~)-2-[1-(~~ethoxy-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(t)-2-[~,-(3~ethoxy~2~hydroxypropyl)-~,5-dimethoxy-1H-indol-3-yl]-3-(1H-indal~3-yl)-maleinimide;
(~)-2~[1-(3~ethoxy-2-hydroxypropyl)-5,6-dime~thoxy-IH-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-acetylamino-1-(3-ethoxy-2-hydrnxyp~opyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-acetylamino-1-(3-ethoxy-2-hydroxyp~opy~1)-1H-indal-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)°2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3°yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-amino-1~(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-['7-amino-1-(3-ethoxy-2-hydraxypropyl)-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(3-ethoxy-.2-hydraxypropyl)-iH-indol-3-yl]-3- ( ~.H-indol-3-yl ) -maleinim).de;
(-h)~2-[6-benzyloxy-1-(3°ethoxy-2-hydroxypropyl)-1H-indol°3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(3~ethoxy-Z-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
_5Q_ (+)-2-[4-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-Z-(~-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[6-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[5-chloro-1-(3-ethoxy-Z-hydroxypropyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide; v (+)-2-[6-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(~.H-indol-3-yI)-maleinimi.de;
(+)°2-[1~(3-ethoxy-2-hydroxypropyl)-4-fluoro-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~-[1-(3-ethoxy-2-hydroxypropyl)-6-fluoro-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethaxy-2-hydroxypropyl)-9-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropylj-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-~-hydroxyprapylj-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yI]-3-(iH-indol-3-ylj-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-7-trifluoromethyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-ylj-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropylj-5-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-?-methoxy-1H-indol-3~yl]-3-(1H-indol-3-yl)~-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydraxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(+j-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
-5z-(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-6,7-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-.2-[1-(3-ethoxy-2-hydroxypropyl)--4-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-Z-hydroxypropyl)-6-methyl-iFd-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-~-hydroxypropyl)-5-vitro-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-vitro-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-vitro-iH-indol-3-y1]-3-(iH-indol-3-y1)-maleinimide;
(+)-~-[1-(3-ethoxy-2-hydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indo7.-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidea (+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
(-)-2-[b-acetylamino-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(_}-2-[7-aoetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-amino-1-(3-ethoxy-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol~3-yl)-maleinimide;
(-}-2-[6-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidei (-)-2-[?-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-( 1H-indol-3~yl ) -maleinimide;
(-)-~~[4~benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1FI-indol-3-y1)-maleinimide;
- 54 - ~~c)~~(9 (-)-2-[6-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-(7-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-bromo-1-(3-ethoxy-2-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5--bromo-1°(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-bramo-1-(3-ethoxy-2-hydroxypropyl)-1H-indolp3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-(3-ethoxy-z-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(3-ethoxy-2-hydroxyprapyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[7-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-~iuoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro-iH-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-~luoro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-hydroxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-hydroxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methoxy-iH-indol-3-yl]-3-(lH~indol--3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(iH-i.ndol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
_56-(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(~.H-indol-~-yl)-maleinimide;
(-)-2-[Z-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy--1H- indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,7-methylendioxy-aH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(-}-2-[1-(3-ethoxy-2-hydroxypropyl}-5-methyl-1H-indol-~-yl]-3-(2H-indol-~-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-~-[1-(3-ethoxy-2-hydroxypropyl)-?-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl}~maleinimide;
(-)°2-[1-(3-ethoxy-2-hydroxypropyl)-6-vitro-1H-indol-3-y:L]-3-(1H-indol-3-y1)-maleinimideF
(-)-2-[~:-(3-ethoxy-2-hydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-x-hydroxypropyl)-4-methylthio-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[:1-(3-ethoxy-2-hydroxypropyl}-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 5? -(-)-2-[1-(3-ethoxy-~-hydroxypropyl)-6-methylthio-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,~-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yI]-3-(1H-indol-3~yl)-maleinimide;
(-)-~~[1-(3-ethoxy-2-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-acetylamino-1-(2-diethyZaminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[6-acetylamino-1-(2-diethylaminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-acetylamino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~4-amino-1-(~-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[5-amino-1-(2-diethylaminoethyl)-1H-indol~3-yl]-3-(1H-indol-3~yl)-maleinimide:
z-[6-amino~1-(2~diethylaminoethyl)-1H-indol-3~yl]~3-(1H-indol-~~yl)-maleinimide;
2-[7-amino-1-(2-diethylaminoethyl)-1H-indol~3-yl]-3-(1H-indol-3-yl)~maleinimide;
2-[4-benzyloxy-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
z-[5-benzyloxy-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-benzyloxy-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-benzyloxy-I-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1.-(2-diethylaminoethyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[4-chloro-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[5-ahlaro-1-(2-diethylaminoethyl)-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[6-ahloro-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-[7-chloro-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-fluoro-1H-indol-~°yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-b-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
x-[1-(~-diethylaminoethyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-a-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-b-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-trifluoromethyl-2H-indol-3-yl]-3-(1H-indoi-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-b-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-trifluoromethyl-1H-indol-3-yI]-3-( 1H-indol-3-yl ) -maleinimide;
2-[~,-(2-diethylaminoethyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(~-diethylaminoethyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
60 _ i~~~ ~
2-[1-(2-diethylaminoethyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[1-(2-diethylaminoethyl)-7-methoxy-1H-indol-~-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(z-diethylaminoethyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[1-(2-diethylaminoethyl}-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl}-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-4-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[1-(2-diethylaminoethyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-methyl-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(2-diethylaminoethyl)~4-vitro-1H~indol-3°yl]-3-(1H-indol-3-yl)-maleinimide;
2~[1-(2~diethylaminoethyl)-5-vitro~1H-indol-3-yl]~3~(1H-indol-3-yl)-maleinimide;
2~[1~(2~diethylaminoethyl)-6~nitra~1H~indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
2-[1~(2-diethylaminoethyl)~7-vitro-1H-indol-3~yl]-3-(1H-indol-3-yl)-maleinimide;
_, -61-2-[1-(2-diethylaminoethyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-methylthio-1H-indol-3-yl]-~-(1H-indol-~-yl)-maleinimide;
2 -[1-(2-diethylaminoethyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-acetylamino-~-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol- 3-yl)-maleinimide;
(~)-2-[5-aaetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-aaetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[7-acetylamino-1-(3-diethylamino-2-hydraxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-Z-[4-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(~)-2-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
a ~~~a ~a (--1)-2-[6-amino-1-(~-diethylamino-2-hydroxypropyl)-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø)-2-[7-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-benzyloxy-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(~.H-indol-3-yl)-maleinimide;
(~)-2-[7-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-~.H~-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-bromo-1-(3-diethylamino-2-hydraxypropyl)-1H-indol-3-yl]-3~(~.H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-bramo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[4-ahlara-1-(3-diethylamino-2-hydraxyprapyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(~)-2~[5-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(t)-2-[6-ahloro-1-(3-diethylamino-2-hydroxyprapyl)-3H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
__~, .- 6 3 -(~)-2-[?-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-~-hydroxypropyl)-5-fluoro-1H-indal-3-yl]-3-(~.H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamina-2-hydroxypropyl)-6~~fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-?-fluoro-1H-indol-3-yl]-3-(xH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(t)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-hydroxy-LH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1-)-~-[1-(3-diethylamino-2-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-?-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[1-(3-diethylamino-2-hydraxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-~-(1H-indol-3-yl)-maletnimide;
(t)-2-[1-(3-diethylamino-x-hydroxypropyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-?-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl}-7-methoxy-1H-indol-3-y1J-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,~-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(--1)-2-[1-(~-diethylamino-2-hydroxypropyl)-6,7-methylendioxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-{3-diethylamino-2-hydroxypropyl}-4-methyl-1H-indol-3-yl]-3-(1H-indol~3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl}-5-methyl-1H-indol-3-yl)-3-{1H--indol-3-yl)-maleinimide:
(~)-2-[2-(3-diethylamino-2-hydroxypropyl)-6-methyl-1H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methyl-1H-indol-3-yl]-a-(1H-indol-~-yl)-maleinimide;
(t)~2~[1~(3-diethylamino-2-hydroxypropyl)-4~nitro-1H-indol~3-yl ] -3- ( ~.H~indol-3-yl ) -maleinimide;
(t)~2-[1-(3-diethylamino~2~hydroxypropyl)-5~nitro~1H-indol-3-yl]-3-(1H~indol-3-ylj-maleinimide;
(t)-2-[1-(3-diethylamina-2-hydroxypropyl)-6-nitro-1H-indol-3~
yl]~~~(1H-indol-3-yl)-maleinimide;
65 _ ~~~~~~~i (~)-2-[1-(3-diethylamino-2-hydrbxypropyl)-7-nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydraxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indal-3-yl)°maleinimide~
(--1)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[~.-(~-diethylamino-2-hydroxypropyl)-5,6-dimethoxy-3H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3°(1H-indol-3-yl)-maleinimide;
(+)-2-[4-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)~maleinimide:
(+)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)--2-[6-acetylamino-1-(3-diethylamino-2~hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[7-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-~-yl)-maleinimide;
(+)-2-[4-amino-1-(3-diethylamino-Z-hydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
-~~-(+)-2-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(+)-2-[6-amino-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-['3-amino-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-Z-[4-benzyloxy-1.-(3-diethylamino-x-hydroxypropyl)-1H-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide:
(+)-2-[t-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)~1H-~indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[:4-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-Z-[5-bromo-1-(~-diethylamino-2-hydroxypropyl)-1H-indol-~-ylj-3-(1H-indol-3-yl)--maleinimide;
(+)-2-[6-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol~3-ylj-3-(1H-indol-3-yl)-maleinimide;
(-H)-2-[~-chloro-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-ylj-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-~.-(3-diethylamino-2-hydroxypropylj-iH-indol-3-y1j-~-(xH-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(3-diethylamino-~-hydroxypropyl)-iH-indol-3-yl]-3-{1H-indol-3-y1)-maleinimidet (+)-2-[T-chloro-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yI]-3-{1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydraxypropyl)-~-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
{+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-fluoro-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-mal~inimide;
(+)-2-[1-(3-diethylamino-2 -hydroxypropyl)-7-fluoro-1H-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-hydroxy-iH-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-~-hydroxypropyl)--5-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-trifluoromethyl-iH-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamina-2-hydroxypropyl)-5-trifluoromethyl-iH-indal-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-trifluaromethyl-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
-~8-(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-trifluoromethyl-~.Fi-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyi)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2=hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(~-diethylamino-2-hydroxypropyl)-6-~methoxy-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-~methoxy-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-~)-2-[1-(3-diethylamino-Z-hydroxypropylj-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,s-methylendioxy-1H-indol-3-y1]-3-(2H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypr~pyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)'2-[1-(3-diethylamino-2-hydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-Z-[1-(3-diethylamino-2-hydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-3ndol-~-yl)-maleinimide;
(+)-2-[1~(3-diethylamino-2-hydroxyprapyl)-l-methyl-1H-indol-3-yl]-~-(1H-indol~3-yl)~~maleinimide:
(+)-2-[1-(3-diethylamino-a-hydroxypropyl)-~-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-s-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyi)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-methylthio-1H-indol-3-yI]-3-(1H-indol-3-yl)-~naleinimide:
(+)-2~[1-(3-diethylamino-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[Z-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-3H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3~-yl]-3-(1H-indol-3-yl}-maleinimide;
(+)-2-[1-(3-diethylamina-2-hydroxypropyl}-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-«)-2-[4-acetylamino-1-(3-diethylamino-2-~hydroxypropyl)-1H~
indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)--2-[6-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
-~o-(-)-2-(7-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(~-diethylamino-2-hydroxypropyl)-1H-ii7dol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-Z-[4-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-lH~indol-3-yl]-3-(1H-indol-3-yl)-maleinimid~;
(-)-2-[5-benzyloxy-7.-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-malei~nimide;
(-)-2-[4-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2~[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl~-3-(1H-indol-3-yl,)-maleinimide;
(-)-2-[6-bromo-1-(3-diethylamino-Z-hydxoxypropyl)-1H-indol-3-yl]-~~(1FI-indol-3-yl)-maleinimidm;
(-)-2-[7-broma-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
...., - m -(-)-2-[4-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(-)_2-[5-chloro-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl}-maleinimide;
(-)°2-[7-chloro-1-(3-diethylamino-~-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-fluaro-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[x-(3-diethylamino-2-hydroxypropyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[1-(3-diethylamino-2-hydroxypropyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[~.-(3-diethylamino-2-hydroxypropyl}-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-~-hydroxy-1H-indol-3-ylJ-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(~-diethylamino-~-hydroxypropyl)-6-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-}-2-[1-(3-diethylamino-2-hydroxypropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-tri~luoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-trifltaoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimids;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yI)-malsinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-~1-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-msthoxy-1H-indol-3-yl]--3-(1H-indol-3-yl)-malsinimide;
(-)-~-[1-(3-diethylamino-2-hydroxypropyl)-6-methoxy-~.H-indol-3-yl]-3-(1H-indol-3-y1)-maleirilmide;
(-)-2-[1-(3-disthylamino-2-hydroxypropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)~2°[1-(3-diethylamino-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-disthylamino-2-hydroxypropyl)-6,7-msthylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-4-methyl--1H-indol-3-yl]-3-(1H-indol-3-yl)-malsinimicle;
(-)-2-[1-(3-disthylamino-2-hydroxypropyl)-5-methyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-malsinimide:
(-)-~-[1-(3-diethylamino-2~hydroxypropyl)-6-methyl-1H-indol-3-yl~-3-(1H-indol-3-yl)-malsinimids;
_ 7~ _ ~~~ U
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-methyl-1H-indol-3--yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[1-(3-diethylamino-2-hydroxypropyl)-~-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-nitxo-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-Z-hydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-7-vitro-iH-~indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)_~_methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(~-diethylamino-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-6-methylthio-1H-indol-3-yl~-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl}-7-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-z-hydroxypropyl)-4,5-dimethoxy-1Ef-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[~.-(3-diethylamino-2~-hydroxypropyl}-5,6-dimethaxy-iH-indol-3-yl]-3-(1H-indol-3~-yl)-~maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl}-6,7-dimethnxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[4-acetylamina-1-(3-diethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-~4-2-[5-acetylamino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-acetylamino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-amino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[5-amino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-benzyloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-ben2yloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide:
2-[6-benzyloxy-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-benzyloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide:
2-[5-bromo-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
_, - 75 -2-[6-bromo-1-(3-diethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[4-chloro-1-(3-diethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~-chloro-1-(3-diethylaminopropyl}-1H-indol-3-yl]-3-(~.H-indol-3-yl}-maleinimide;
2-[6-ahloro-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-diethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-(1.-(3-diethylaminopropyl)-4-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl}-6-fluaro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1~(3-diethylaminopropyl)-4~hydroxy-1H~indol-3-yl]-3-(~.H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[~.-(3-diethylaminopropyl)-~-hydroxy-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-hydroxy-1H-°indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-trifluoromethyl-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[3.-(3-diethylaminopropyl)~6-trifluoromethyl-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-7-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl}-4-methoxy-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopxopyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5,~-methylendioxy-1H-indol-:3-yl]-3-(1H-indol-3-yl}-maleinimide:
2-[1-(3-diethylaminopropyl)-6,7-methylendiaxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methyl-1H-indol-3-y1]-3-(1H-indol-:i-yl)-maleinimide:
~.._, - ~~ -2-[1-(3-diethylaminopropyl)-6-methyl-1H-indol-3-yl]-s-(a.H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(a°diethylaminopropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-6-vitro-1H-indol-3-yl]-3-(LH-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep 2-[3,-(3-diethylaminopropyl)-9--methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-diethylaminopropyl)-5-methylthio--1H-indol-3-yl]~3-(1H-indol-3-yl)-~maleinimide:
2-[2-(3-diethylaminopropyl)-6-methylthio-1H-indol-3-yl]--3-(1H-indol-3-y1)-maleinimide;
2-[1-(3-diethylaminopropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[2-(3-diethylaminopropyl)-4,5~dimethoxy-1H-indol-3-yl]-~3-(1H-indol-3-yl)-maleinimide:
2-[1-(~-diethylaminapropyl)-5,6-dimethoxy-1H-indoi-3-yl]-3-(1H-indol-3-ylj-maleinimide;
2-[1-(3-diethylaminopropyl)-c,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~~.J~~~' _ ,8 _ 2-[4-acetylamino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[5-acetylamino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[?-acetylamino-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3--y1)-maleinimide;
2-[?-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-benzyloxy-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[7-benzyloxy-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-ethylaminopropyl)-1H-$ndal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
~w~
_ 79 2-[5-bromo-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-ethylaminopropyl)-iH-indol-3-yl?-~-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[4-chloro-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-ethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-ethyiaminopropyl)-iH-indol-3-yl]-3-(iH-:indol-3-yl)-maleinimide;
2-[7-ahloro-1-(3-ethylaminopropyl)-iH-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-~-fluoro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-fluaro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
z-[1-(3-ethylaminopropyl)-7-fluoro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[1-(3-ethylaminopropyl)-4-hydroxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-$Q-2-[1-(3-ethylaminopropyl)-6-hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-hydroxy-1H-indol-3-yl]-3-(1H-indol--3-yl)-maleinimide;
2-[I-(3-ethylaminopropyl)-4-trifluoromethyl-1H-indol-3--yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-trifluaromethyl-1H-indol-3-yl]-3-( 1H-indol-3-yl) -maleir~imide;
2-[1-(3-ethylaminopropyl)-7-trifluoromethyl-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4-methoxy-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-methoxy-2H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-methoxy-2H-indol-3-yl]-3-(1H-~indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4,5-methylendioxy-1H-indol-3-y1]-3-( 1H-indol-3-yl ) -maleinimide;
2-[2-(3-ethylaminopropyl)-5,6-methylendioxy-1H-indol-~-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-2-[Z-(3-ethylaminoprapyl)-4-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-f>-methyl-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethyl.aminopropyl)-7-methyl-1H-indol--3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[2-(3-ethylaminopropyl)-4-vitro-iH-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4-methylthio-3H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methylthio-1H-indol-~-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-6-methylthio-iH-indol-3-yl]-~~-(1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-7-methylthio-1H-indol-3-yl)-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylam.inopropyl)-4,5-dimethoxy-1H-indol-~-yl]-3-(1H-indol-3-yl ) -malei~rimide;
- g2 - ~v:~~~~~
2-[1-(3-ethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
a-[a.-(3-ethylaminopropyl)-6,7-dimethoxy-1H-indol-3-yl]-~-(~.H°
indol-3-yl)-maleinimide;
(f)-2-[4-acetylamino-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-Z-[6-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
(~)-2-[4-amino-1-(2-hydroxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-benzyloxy-~.°(2-hydroxy-3-dimethylaminoprapyl)-1FI-indol-3-yl]_3-(iH-indol-3-yl)-malein~.mide;
(t)-2-[5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-~.H-indol_3-yl]-3-(~.H-indol-3-yl)-maleinimide;
~3 -(~)-2-[7-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3~
yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[6-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-bromo-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)°~maleinimide;
(~)-2-[5-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[6-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-~-(iH--indol-3-yl)-male3nimide;
(~)-2-[4-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[5-~luoro-1-(2-hydroxy-3-dimethylamia~opropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[6-~luoro-~,--(2-hydroxy-3-dimethyl~minopropyl)-1H-indol-3-yl]-a-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-~1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
- 8~ -(~)-2-[4-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[6-hydroxy-1-(2-hydroxy-3-dimethylaminopxopyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1.H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(--1)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-2-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydraxy-~-dimethylaminopropyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminapropyl)-5-methoxy-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(f)-2-[1-(2-hydroxy-a-dimethylaminopropyl)-4,5-methylendioxy-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 85 - .~ ~ J ~~
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[1-(2-hydroxy-3-dimethyiaminopropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-~5-methyl-1H-indol-3-yl]-3-(1H-indol-~-yl)°maleinimide;
(-i-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methyl-1H-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(a-hydroxy-3-dimethylaminopropyl)-4-vitro-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminogropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~y-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-a-yI]-3-(1H-indol-3-yl)-maleinimide;
(i)-2-[~.-(2-hydroxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1.-(2-hydroxy-3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol°3-yl)-maleinimide;
(ø)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol -3-yl)-maleinimide:
(+)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[6-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[7-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-amino--1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
(+)-2-[5-amino-1-f,2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+}-2 -[6-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7 -amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~--yl)-maleinimide:
(+)-2-[4-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~-y1)-maleinimide:
-(+)-2-[5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(+)-2-[s-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(+)-2-[7-benzyloxy-1-(~-hydroxy-3-dimethylaminoprapyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol--3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-bromo-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(~-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(+)-~-[4-ahloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(~-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(+)-2-[6-ahloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chlora-1-(~-hydroxy-3-dimethylaminoprapyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-fluoro-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-~-dimethylaminopropyl)-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
_88_ (+)-2-[6-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)--1H-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-Z-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-:indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)~iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[~-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(+)-2-[?-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
(*)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-+~)-2-[1~(2-hydroxy-3-dimethylaminopropyl)-5-methoxy-1H~indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(*)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-malelnimide;
(+)-2-[1-(2-hydroxy-~-dimethylaaninopropyl)-7-methoxy-7.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[1-(2-hydroxy-3-dimethylaminogropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(~.H-indol-3-yl)-maleinimide:
(+)-2-[7.-(2-hydroxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl ] -3- ( 3.H-indol-3-yl ) -maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-y1]-3-(1H-indol-3-y1)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methyl-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methyl-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminoprapyl)-7-methyl-~.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)--~-[1-(2-hydroxy-3-dimethylam~.isopropyl)-6-vitro-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinirnide:
(+)-2-[~.-(2-hydroxy-3-dimethylaminopropyl)-7-vitro-1I~I-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[~.-(2-hydroxy-a-dimethylaminopropyl)-4-methylthia-1H-indol-3-yl)-3-(1H-indol-3-yl)-male9.nimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-dimethoxy-1H°
indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(_)_~_[~_acetylamino-1-(2-hydrdx~-~-dimethylaminapropyl)-1H-indol--3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinim~.de;
(-)-2-[7-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)--iFi-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-amino~1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol~3-yl]-3-(1,H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2-hydroxy-3-dimethy~.am3nopropyl)-iH-indol-3-y1]-3-(~.H-indol-~-yl)-maleinimide:
(-)-2-[6-amino-1-(2-hydroxy-3-dimethylaminopropyl)-a.H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
- ~~.~.c'~~~~J
(-)-2-[7-amino-~.-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3- ' yl]-~-(1H-indol-3-yl)-maleinimide;
(-)-2-[~-benzyloxy-1-(2-hydraxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydraxy-3-dimethylaminopropyl)-iH-indal-3-yl]-3-(2FI-indol-3-yl)-maleinimide:
(-)-2-[6-benzyloxy-1-(2-hydraxy-3-dimethylaminaprapyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(~-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indal°3°yl)-maleinimide;
(-)-2-[4-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-d~.methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)~2-[5-chloro-1-(2-hydraxy-3-dimethylaminoprapyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
(~)-2-[6-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(-)-2-[7-chlora-1-(2-hydroxy-3~dimethy~.aminapropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-. 9 2 --(-)-2-[4-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol--3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[6-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[7-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-~-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[6-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[7-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)_iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[4-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3_yl]-3~(1H-indol-3-yl)-maleinimide:
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maieinimide:
(-D-2-C6-trifluoromethyl-1-(2-hydroxy-3-dimethylaminoprapyl)~
1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[T-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-1H-fndol-3-yl]-3-(1H-indal-~-yl)-malainim3de:
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methoxy-1H-indol-3-yl]-3~-(1H-~indol-3-yl)-maleinimide;
- 93 - ~r~~?~~~
(-)-2-[1-(2-hydraxy-3-dimethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)°maleinimide;
(-)°2-[1-(~-hydroxy-3-dime~thylaminopropyl)-6-methoxy-1H-indol--3-y1]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-}-2-[1-(2-hydroxy-3-dimethylaminoprapyl)--4,5-methylendioxy-~.H-indol-~-yl]-3-(1H-indoi-3-yl}-maleinimide;
(_)_2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methyl-1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
(_)_2_[1.:(z-hydroxy-3-dimethylaminopropyl)-5-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydraxy-3-dimethylaminopropyl)-4-vitro-iH-indal-3-yl]-~-(1H-indol-~-yl)-malein3,mide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-iH-indol-a-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- u~ ~" ~, ,r.
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-nitra-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-2H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)~2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylama.nopropyl)-6,7-dimethoxy°iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-acetylamino-1-(2-hydroxy-3-(~1-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2-hydroxy-3-(4-morphalino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)~2~[7-aaetylamino-1-(2-hydraxy-3-(4-morpholino)prapyl)-1~I-indol-3-yl]~3-(1H-indol-~-yl)-maleinimide;
(t)-2-[4-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-~5-(~)-2-[5-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[6-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl}-iH-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(~)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-benzyloxy-1-(Z-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3°(1H-indol-3-yl)-maleinimide:
(~)-2-[7-benzyloxy-1-(~-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
{~)-2-[4-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(*)-2-[6-bromo-1-(2-hydroxy-3-{4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-broma-1-(2-hydroxy-~-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2~[4-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-2H-indol-3-yl]-3-(~.H-indol-~-yl)-maleinimidet (~)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-.lgi-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(ZH-indol-3-yl)-maleinimide;
(~)-2-[6-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1-)-2-[7-fluoro-1-(2-hydroxy-3-(4amorpholino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-hydroxy-1-(2-hydroxy-3-(~-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maie.inimide;
(~)~2-[5-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-i-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-hydroxy-~-(4-morpholino)propyl)-~.H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(i-)-2-[6-trifluoromethyl-1-(2-hydroxy-~-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~n .~, ~?
(~)°2-[7-trifluoromethyl-1-(2-hydroxy-3-(4-morpholina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep (~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimidet (~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-1H-indol--3-yl]-3-(iH-indol-3-yl)-maleinimidet (~)-2-[1-(~-hydroxy-3-(4-morpholino)propyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-methylendioxy_ 1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morphalino)propyl)-4-methyl-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methyl-1H-:Lndol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(a-morpholino)propyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-vitro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-nitre-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-G-nitro-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydraxy-3-(4-morpholino)propyl)-7-nitre-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(~-morpholino)propyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-methylthio-1H-indol-3-yl]-3-(7.H-indol-3-yl)-maleinimide;
(~)-Z-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(Z-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(*)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-~-yl)°maleinimide;
(*)-2-[4-acetylamino-1-(2-hydraxy-3-(~-marphalino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(*)-x-[5-acetylamino-1-(2-hydroxy-3-(~-mnrpholino)propyl)-1H-~.ndol-3-yl]-3-(1H-indol-3-yl)-maleini~n,ide;
(+)-2-[6-acetylamino-1-(2-hydroxy-3-(~-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
((~~ ~9; ~,A~
- ~ ~ ~ eJ~ Q.
(+)-2-[7-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-{2-hydroxy-3-(4-morpholino)propyl)-1Ii-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[~-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3°yl]-3-(1H-indol-3-yl)-maleinimides (+)-2-[6-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-hydroxy-3-{~-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+) -2- [ 5-bromo-1- ( 2-hydroxy-3- { ~-morphol ino) propyl ) -1Fi-indol-3-y1]-3 -(iH-indol-3-yl)-maleinimide;
(+)-Z-[6-bromo-1-(2-hydroxy-3-(~6-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[7-bromo-1-(2-hydroxy-3-(4-morpholino)propy:l)-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
o - ~~r~
(+)-2-[~-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol~
3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chloro-1-(2-hydroxy-3-(4-morpholina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~-[4-~luoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl)-2H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(+)-2-[7-~luoro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-hydroxy-Z-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-2-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(1H-indo~.-3-yl)-~naleinimidet (+)-2-[7-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
(+)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(~-morpholino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[6-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl}-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide:
(+}-2-[7-trifluoromethyl-1-(2-hydroxy-3-(~-morpholino)propyl}-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-marpholino)propyl)-6-methoxy-iH-indol-3-yl]-3-(IH-indol-3-yl}-maleinimide:
(+)-2-[1-(2-hydroxy-~-(~-morphoiino)propyl)-7-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(~-hydroxy-3-(4-morpholino)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-z-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-methylendinxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methyl-iH°-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morphcalino)propyl)-5-methyl-iH-indol-3-yl]-3-(iH-indol-3--yl)-malein~.mide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-methyl-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydraxy-3-(4-morpholino)prapyl)-7-methyl-1H-indol-3-y1]-3t-(1H-indol-3-yl)-maleinimide:
(+)-2-[1~-(2-hydraxy-3-(4-morpholino)propyl)-4-nitra-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-vitro-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholina)propyl)-7-vitro-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-methylthia-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)~maleinimide:
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(+}-2-[1-(2-hydroxy-3~(4-morpholina)propyl)-5,6-dimethoxy~1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6,7-dimethaxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-acetylamino-1-(2-hydroxy-3-(4-marpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(h-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(°)°2-[7-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-}-2-[5-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-amino-1-(2-hydroxy-~-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[7-amino-1-(2-hydroxy-3-(4-morpholino}propyl}-1H-indol«3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[4-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-i~enzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[s-benzyloxy-1-(Z-hydroxy-3-(4-morpholino)propyl}-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(-)-2-[7-benzyloxy-1-(2-hydroxy-3-(4-morpholino}propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(-}-2-[4-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholino}propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
;., - log -(_)_2-[6-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[7-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)~-2-[4-chloro-1-(2-hydroxy-3-(4-morphalina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-chloro-1-(2-hydraxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[6-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide:
(-)-2-[7-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-fluoro-1-(2-hydroxy-3-(~-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide:
(-)-2-[5-fluoro-1-(2-hydroxy-3-(4-morphalino)propyl)-iH-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide:
(-)-2-[6-fluoro-1-(2-hydraxy-3-(4-marpholina)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-fluoro-1-(2-hydroxy-3-(~-marpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-hydraxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-hydroxy-1-(Z-hydroxy-3-(4-marpholino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide:
(-)-2-[~-hydroxy-1-(2-hydroxy-3-(4-morpholina)prapyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[7-hydroxy-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2-hydroxy-3-(4~~morpholino)propyl)-1H-indol-3-yl)-3-(1H-indol-~-yl)-maleinimide;
(-)-2-[7-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholin~)propyl)-4-methoxy-1Fi-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
(-)-2-[1-(2-hydraxy~3-(4-morpholino)propyl)-5-methaxy-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-G-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morphalino)propyl)-7-methoxy- 1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-methylendioxy-1H-indal-3-y1)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-marphalino)propyl)-5,G-methylendioxy-1H-indol-3-yl)-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-marphalino)propyl)-G,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-methyl-1H-indol-3-yl]-a-(1H-indol-3-yl)-maleinimide;
- so6 -(-)-2-[1-(2-h.ydroxy-3-(4-morpholino)propyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(~°morpholino)propyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-?-methyl-1H-indol-3-yl]-3-(1H--indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1~(2-hydroxy-3-(4-morpholino}propyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-vitro-1H-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-?-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-~-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-1H-indol-3-yl]-3-(~H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morphalino)propyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-?-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinim3.de;
(-)-2-[1-(2-hydroxy-3-(4-morpholino}prapyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
- to (-)-2-[1-(~-hydroxy-3-(4-morphalino)propyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(--1)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[6-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-raaleinimide:
(~)-2-[7-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[6-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(_+)-2-[7-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H°-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(~)-2-[4-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)~-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(a)-2-[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)~-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~j-2-[6-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[7-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indal-3-yl]-3-(2H-indol-3-y1)-maleinimide:
- zo~ - ~:~~J~
(~)°2-[4-bromo-1-(2-hydroxy-3-(1-piperidino}propyl)-3.H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo~1-(2~hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-bromo-1-(2-hydroxy-3-(1-piperidino}propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[7-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[4-chloro-~.-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
(~)-2-[5-chloro-1-(2~hydroxy-3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-~-[6-chloro-1-(2-hydroxy-3~(1-piperidino)propyl)-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-chloro-1-(2-hydroxy-3-(1~piperidino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)~maleinimide;
(~)-2-[4-fluoro-1-(2-hydroxy-3-(1~piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(2-hydraxy-~-(1-piperidino}propyl}-1H-indol-3-yl]-3~(1H~indol-3-yl)-maleinimide;
(t)-2~[6-fluoro-~.~(2~hydroxy-3~(1~piperidino)propyl)-1H-indol-3~yl]~3~(1H-indol~3~yl)-maleinimide;
(t)~2~['7~fluoro~2-(2-hydroxy~3~(~.-piperidino)propyl)~1H~indol-~-yl]-3-(1H-indol~3-yl)-maleinimide;
(t)-2-[4-hydroxy~1-(2-hydroxy~~~(1~piperidino)propyl)~1H~indol-3-yl]-3-(~.H~indol-3~yl)-maleinimide;
- to (--1)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[7-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3~y1)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-trifluoromethyl-1-(z-hydroxy-3-(~.-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(1)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[~.-(2-hydroxy-3-(1-piper].dino)propyl)-7-mathoxy-1H-indol-~-yl~-3-(iH-indol-3-yl)-maleinimide:
(~)-~-[1-(2-hydroxy-3-(1-piperidino)propyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,C-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
- llfl -(~)-2-[1-(2-hydroxy-3-(1-piperidino}propyl}-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-~-methyl-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[~.-(2-hydroxy-3-(1-piperidino}propyl)-5-methyl-1H°indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[2-(2-hydroxy-3-(1-piperidina}propyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~}-2-[1-(~-hydroxy-3-(1-piperidino)propyl}-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide~
(~)-2-[1-(2-hydroxy-3-(~.~piperidino)propyl)-4-vitro-1H-indol-3-yl]-3-(3H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-~5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-vitro-1.H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methylthio-1H~
indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(1-piperidino)prapyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-.3-yl)-maleinimide~
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinirnide;
(v)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
- 111 - ~~e (~)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-4,5-dimethoxy-iH-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-z-[1-(z-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(z-hydroxy-3-(1-piperidino)propyl)-6,7-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-acetylamino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-acetylamino-1-(z-hydroxy-3-(1-piperidino)propy~.)-iH-indol-3-yl.]-3-(iH-indoi-3-yl)-maleinimide;
(+)-2-[7-acetylamino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-z-[4-amino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-amino-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimiua;
(+)-2-[7-amino~1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(z-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-z~[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
- 112 ° ~) e) ~ ~ ' (+)-2-[6-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(2-hydroxy-3-{1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~2-[7-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(2-hydroxy-3-{1-piperidino)propyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleiniinide;
(+)-2-[7-chloro-1-(2-hydroxy-3-{1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-~-(1-piperidino)propyl)-1H-indol-3-yl]-~-(1H-indol-~-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-ms-(+)-2-[7-fluoro-1-(2-hydroxy-~-(7.-piperidino)propyl)-1H-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(+)-2-[~3-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-hydroxy-1-(2-hydraxy-3-(1-piperid:Lno)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(~.-piperidino)propyl)-1H-indol-3-yl]-3-(1N-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-3.-(2-hydroxy-3-(2-piperidino)propyl)-2H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-trifluoromethyl-Z-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol°3-yl]-3-(1H°indol-3-yl}~maleinimide;
(+)-2-[1-(2-hydroxy-a-(1-piperidino)propyl)-4-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-x-[1-(2-hydroxy-3-(5.-piperidino)propyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2~[1-(2-hydroxy-3-(1-piper].dino)propyl)-6-metkioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy~3-(1-piperidino)propyl)-7-methoxy-2H-indol~
3-y1]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,~-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[~.-(2-hydroxy-3-(1-piperidino)propyl}-6,7--methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(+)-2-[1-(2-hydroxy-3-(1-piperidino)progyl}-6-methyl-iH--indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(+j-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-7-methyl-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+}-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-vitro-iH-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl}-6-vitro°1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet (+)-2-[1-(z-hydroxy-3-(1-piperidino)propyl}-7-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinim:Lde;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+) -2- [ 1- ( 2-hydroxy.-3- ( 1-piperidino) propyl } --5-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-methylthio-1H-indol-3-yl]-3 -(1H-indol-3-yl)-maleinimider (+)-2-[1-(2-hydroxy-~-(1-piperidino)propyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)prapyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[7-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-~-[4-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[s-amino-1-(2-hydroxy_3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[~-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(~-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[4-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)~2-[5-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-yl]~~3-(1H-indol-3-yl)-maleinimide;
(-)-2-[f-bromo-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-(2-hydroxy-~-(1-piperidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(~-hydroxy-3-(1-piperidino)propyl)-iH-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propylj~lH~indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-chlaro-1-(2-h:ydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)~2-[7-chloro~1-(2-hydroxy-3~(1-piperidino)propyl)-1H-indol-~-yl]~3~(1H-indol~3-yl)~maleinimide;
(-)-2-[4-fluoz~o-1~(2-hydroxy-3-(1-piperidino)propyl)-iH-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
- 11? -(-)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-fluoro-1-(2-hydroxy-3-(~.-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-hydroxy-1-(2-hydroxy-3-(1-piperldino)prapyl)-?._ hydroxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-)-2-[4-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-4-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-6-trifluoromethyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methaxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[~.-(2-hydraxy-3-(1-piperidino)propyl)-5-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
L m, - ms -(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-s-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-methoxy-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,s-methylendioxy-1H-indol-3-y1]-3-(1H-indol-3-yl}-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6,7-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(_)-2-[1-(Z-hydroxy-3-(1-piperidino)propyl}-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)_~_[1-(2-hydroxy-3-(1-piperidino)propyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-~-vitro-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1~(2-hydroxy-3-(1-piperidi.no)propyl)-5~nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-}-2-[1-(Z-hydroxy-3-(1-piperidino)propyl)-s-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-) -2- [ 1- ( 2-hydroxy-3- ( ~.-piperidino} propyl ) -7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
- 119 - ~~~~~.e (-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-methylthio-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methylthio-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimidea (-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(-)-~-[1-(2-hydroxy-3-(1-piperidino)propyl}-7-methylthio-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide:
(-)°2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-dimethoxy-iH-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(°)-2-[1-(2-hydroxy-3-(1-piperidina)propyl)-5,7-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-~)°2-[4-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-mal~inimide;
(~}-2-[6-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimideo (t)-2-[7-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
(i)-2-[4-amino-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(t)-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
- 1~0 - ~~.°~~' (--1)-2-[6-amino-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(~)-2-[7-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø)-2-[4-benzyloxy-1-(~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-~)-B-[6-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[4-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(--1)-2-[6-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(1-)-2-[7-bromo-1-(~,3-dihydroxypropyl)-iH-indol-3-yl]-3-~(iH-indol-3-yl)-maleinimide;
(t)-2-[4-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(:~)-2-[5-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[6-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 1~1 -(~)-2-[7-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(--1)-2-[4-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(~,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1)-2-[6-fluoro-1-(2,3-dihydroxypropyl}-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-fluora-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-hydroxy-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
(ø)°2-[5-Ydydroxy-1-(2,3-dihydroxypropyi)-1H-indol-3-yl]-~3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2,3-dihydroxypropyl)--iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2,3-dihydroxypropyl)-1H-indal~3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t}-2-[5-trifluaromethyl-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-3~ndo1-3-yl)-maleinimide;
(~)-2~[6-tr:Lfluoromethyl~1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-1-(2,3-dihydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-di.hydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol -3-yl]-3°{1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2,3-dihydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(1-)-2-[1-{2,3-dihydroxypropyl)-7-methoxy-1lH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[1-(2,3-dihydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-6,3-methylendioxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide:
(ø)-2-[1-{2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-{1H-indol-3-yl)-maleinimide;
{~)-2-[1-(2,3-dihydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(t)-2-[1-(2,3-dihydroxypropyl)-?-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4-nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-Cl-(2,3-dihydroxypropyl)-5-nitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-6-vitro-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-?-vitro-iH-indol-3-yl]-3-(1H-indol-3-yi)-maleinimide:
(--1)-2-[1-(2,3-dihydroxypropyl)-4-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-lI-I-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-6-methylthio-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(--1)-2-[1-(2,3-dihydroxypropyl)-?-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-2H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-5,5-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2,3-dihydroxypropyl)-6,?-dimethoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+}°2-[4-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[6-acetylamino-~.-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide:
(+)-2-[?-acetylamino-1-(2,3-dihydroxypropyl)-1Fi-indol-3-yl]-3-(1H-indol-3-yl)mmaleinimide:
(+)-2-[4-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+}-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+}°2-[6-amino-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(1H-indal-3-yl}-maleinimide;
(+)-2-[7-amino-1-(2,3-dihydroxypropyl)-1H-indol-°3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[S-benzyloxy-1-(2,3-dihydroxypropyl}-iH-indol-3-yl]-3--(1H-indol-3-yl)-maleinimide;
(+)-2-[6-benzyloxy-1-(2,3-dihydroxypropyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
(+}-2-[5-bramo-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(1H-indal-3-yl)-maleinimide;
(+)-2~[6-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2~[7-brama~1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-chloro-1-(2,3-dihydroxypropyl}-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
- 125 - ~.~c~s~~~s (+)-2-[5-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[s-chloro-1-(2,3-dihydroxypropylj-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+j-2-[4-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3~yl]~3-(1H-indol-3-yl)-maleinimide:
(+j-2-[5-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3--yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2,3-dihydroxypropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimidei (+)-2-[7-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-hydroxy-1-(2,3-dihydroxypropylj-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[s-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]~-3-(1H-indol-3-yl)-maleinimide:
(+j-~-[7-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]--3-(1H-indol-3-yl)-maleinimide;
(+)-2-r4-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimida;
(+)-2-[5-trifluoromethyl-1-(2,3-dihydroxyprapyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- las -(+)-2-[6-trifluoromethyl-1-(z,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-trifluoromethylai-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep (+)-2-[1-(2,3-dihydroxypropyl)-4-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-s-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)~-2-[1-(2,3-dihydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(~,3-dihydroxypropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide~
(+)°2-[1-(2,3-dihydroxypropyl)-°5,6-methylendioxy-1H-indol-3°
yl]-3-(iH-indol-3-yl)-maleinimide:
(+)-2-[1-(2,3-dihydroxypropyl)-6,7-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-~-[1-(2,3-dihydroxypropyl)-~-methyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet (+)-2-[1-(2,3-dihydroxyprapyl)-5-methyl-iH-inds~l-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3~dihydroxypropyl)-s-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimideo (+)-2-[1-(2,3-dihydroxypropyl)-7-methyl-iH-indol-3-yl]-s-(iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihyc~roxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(+)-2-[2-(2,3-dihydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimida;
(+)-2-[1-(2,3-dihydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-7-methylthio-1H-indol-3-yl]-3--(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydraxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[~.-(2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(_)-2-[4-acetylamino-1-(2,3-dihydroxypropyl)--1H-indol-3-y1]-3-(1H-indol-3-y:l)-maleinimide;
(-)-2-[5-acetylamino-1-(~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 12$ - ~.~e.~e~~
(-)-2-[6-aoetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[7~-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[4-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-amino°1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[6-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimideo (-)-2-['7-amino-1-(2,3-dihydroxypropyl}-1H-indol-3-y1J-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-benzyloxy-1-(2,3-dihydraxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-benzyloxy-1-(2,3-dihydroxypropyl)-lH~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
(-)-2-[4-bromo-2-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[5-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-y1]-3-(1H-indal-3-y1)-maleinimidef (-)-2-[6-bromo-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
ed - 1~9 - l~ ~~2' ~~~;~
(-)-2-[?-bromo-1-(2,3-dihydroxypropyl)-1H-indol -3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[?-chloro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-gluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-gluoro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-gluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-gluoro-1-(~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(iH-inc~ol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-{~,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
(-)-2-[?-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
-13~-(-)-2-[4-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-trifluoromethyl-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1~(z,3-dihydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-6-methoxy-1H-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-7-methoxy-iH-indol-3-yl]-3-(1H-indol~-3-yl)-maleinimide;
(-)-~-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-Z-[1-(2,3-dihydroxypropyl)-6,7-methylendioxy-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-(1-(2,3-dihydroxypropyl)-~-methyl-iH-indol-3-yla-3-(iH-indol -3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 131 - ~ e~
(-)-2-[1-(2,3-dihydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-~-[1-(2,3-dihydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(_)_2_[1_(2,3-dihydroxypropyl)-7-vitro-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)°2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(2H-indol-3-yl)-~naleinimide;
(-)_2-[1-(2,3-dihydroxypropyl)-6-methylthio-1H-indol-3-yl]-3-(1H-indo2-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-7-methylthio-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(--)_2-[1-{2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-G,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleiniznide;
.. 132 - ~~_~~:~~a 2-[4-acetylamino-1-(3~-hydroxypropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino°1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[?-amino-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(5-benzyloxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-benzyloxy-1~(3-hydroxypropyl)-1H~indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[7-benzyloxy-1-(3-hydraxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;.
2-[5-bromo-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-ohloro-1-(3-hydroxypropyl)-1H-indol-3~-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-hydroxypropyl)~-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-chloro-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-hydroxypropyl}-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[5-fluoro-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
~-[7-fluoro-1-(~-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[5-hydroxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
13~ -2-(6-hydroxy-1-(3-hydroxypropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[?-hydroxy-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-hydroxypropyl)-5~~trifluaromethyl-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-hydroxypropyl)-6-trifluoromethyl-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[?-trifluoromethyl-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-4-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-f>-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-?-methoxy-1H-indol-3-yl]-3-(iH-indol-3-yl)--maleinimide;
~-[1-(3-hydroxypropyl)-4,5-methylendioxy-1H~indol-3-yl]-3-(1H-indol-3-yly-maleinimide;
2-(1-(3-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3~(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6,?-methylendiaxy-1H-indol-3-yl]-3-(lI-I-indol-3-yl)-maleinimide;
- 13 5 - ~ 'e,n~' 2-[1-(3-hydroxypropyl)-4-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-7-methyl-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-4-vitro-1H-indol-3-yl]-3-(iH-indol~3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-7-vitro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
z-[1-(3-hydroxypropyl)-4-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(1H-indol--3-yl)-maleinimide;
2-[1-(3-hydroxyprapyl)-6-methylthio-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-7-methylthio-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~.~(3-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~~:~ ~~_ 2-[Z-(3-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6,7-dimethoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-[4-acetylamino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-[6-acetylamino-7.i(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
Z-[7-acetylamino-1-(3-isothiocyanatopropyl)-1H-indc~l-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-amino-1-(3-isothiocyanatopropyl)-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide:
2-[5-amino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]°3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1.-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[7-amino-2-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[4-benzyloxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-iso~thiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[6-benzyloxy-1-(3~isothiocyanatapropyl)-1H-indol-3-yl]~3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-1-(3-~.sothiacyanatopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-isothiocyanatopropyl)-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[7-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-isothiacyanatapropyl)-1H-indal-3-yl]-3-°(1H-indol-3-yl)-maleinimide;
2-[5-chlora-1-(3-isothiacyanatoprapyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-chlaro-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-isothiocyanatopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-isothiocyanatoprapyl)-1H-indal-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[5-fluoro-1-(3-isothiacyanatoprapyl)-1H-indol-3-yl]-3-(1H-indal-3-yI)-maleinimide;
2-[6-fluoro-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-fluoro-1-(3-isathiocyanatapropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(3-isothiocyanatopropyl)-1H--indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[5-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3~[1-(3-isothiocyanatopropyl)-4-methoxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-methoxy-1H-indol-3-yl]-maleinimide;
2-(1.H-indol-3-yl)-3-(1-(3~isothiocyanatopropyl)-6-methoxy-1H-indol-3-yl]-maleinimida;
~-(1H-indol-3-yl)-3~[1-(3-isothiocyanatopropyl)-7-methoxy-1H-indal-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
c'?, , i ~~ .~ e~ J
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
z-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-s,~-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[~.-(3-isothiocyanatopropyl)-4-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-6-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yI)-3-[1-(3-isothiocyanatopropyl)-7-methyl-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2 -(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-6-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-7-vitro-1H-indol-3-yl]-maleinimide;
2-(1H~indol-3-y1)-3-[1-(3-isothiocyanatopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-methylthio-1H-indol-3-yl]--maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-isathiocyanatopropyl.)-6-methylthio-1H-indol-3-yl]-maleinimide;
~~~~vd a-2-(1H-indol-3-yl)-3-[1-(3-ZSOthiocyanatopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4,5-dimethoxy-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5,6-dimethoxy-1.H-indol-3-yl]-maieinimide:
2-(~.H-indol-3-yl)-3-(1-(3-isothiocyanatopropyl)-s,7-dimethoxy-1H-indol-3-yl]-maleinimide:
(~)-2-[4-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-acetylamino-1-(2-methoaty-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide:
(~)-2-[6-acetylamino-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-['7-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[4-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-~-(5-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-mal~inimide:
(~)-~-(6-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl~-3-(1FI-indol-3-yl)-maleinimide;
(t)-?.-[7-amino-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[4-benzyloxy-~.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(*)-2-[6-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
(~)-2-[7-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-~)-2-[4-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
(~j-2-[6-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)°2-[7-bromo-1-(2-methoxy-3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-1nd01-3-ylj-maleinimide;
(i)-2-[4-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-ylj-maleinimide:
(~)-2-[6-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~)-Z-[7-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-~luoro-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
_ 142 -(--1)-2-[6-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(t)-2-[4-hydroxy-3-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(--1)-2-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[6-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-iH--indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(~)-2-[4-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-~aleinimide;
(~)-2-[6-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[7-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H°indol--3-yl]-~-(1H-indol-3-yl)-maleinimide;
(t)-2-(1H-indol-3-yl)-3°[4-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(t)-2-(1H-indol-~-yl)-3-[~-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-maieinimide;
(~)-2-(1H-indol-3-yl)-3-[6-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl)-maleinimide;
t j - 143 - ~,~.~~i~~~~
(~)-2-(1H-indol-3-yl)-3-[7-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(x-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-(1-(2-methoxyp3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy~-3-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-maleinimide:
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-y1)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methyl-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methyl-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-nitro-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-m~thoxy-3-dimethylaminopropyl)-5-nitro-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-nitro-1H-indol-3-yl]-maleinimide;
(t)-2-(1H-indol-3-yl)-3-[1-(z-methoxy-3-dimethylaminopropyl)-7-nitro-1H-indol-3-y1]-maleinimide;
(t)-2-(1H-indol-3-y1)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide;
~r~~~=
- 1~4 -(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(--1)-2-(1H-indol-3-yl)-3-[6,7-dimethoxy-i-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-[4-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-I-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[7-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[4-amino-1-(2-methaxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-amina-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-benzyloxy-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-~-[7-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-bromo-1-(2°methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide:
(+)-~-[7-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[4-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-~-(1H-indol-3-yl)-malei.nimide;
(+)-2-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-chloro-1-(2-methoxy-3-dimethylam~.nopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-ahloro-~.-(2-methoxy-3-di.methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-fluoro-1-(2-methoxy-~-dimethylaminopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[7-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-~-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[6-hydroxy-1-(2-methoxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[7-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[4-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-y~.]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(+)-2-[6-trifluoromethyl-3.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide;
(+)-z-(7-trifluoromethyl-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[4-methoxy-1-(2-methaxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
-, - 14? -(+)-2-(1H-indol-3-yl)-3-[5-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-~-[6-methoxy-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2 -(iH-indol-3-yl)-3-[?-methoxy-1-(2-methoxy-~-dimethylaminopropyl)-1H-indoi-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5,6-methylendioxy-iH-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6,?-methylendioxy-iH-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-y1)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-:3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methyl-iH-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-?-methyl-1H-indol-3-yl]-maleinimide;
(+)~2~(1H-indol-3~yl)-3~[1~(~-methoxy-3-dimethylaminopropyl)-4-nitro-iH-indol-3-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-nitro-iH-indol-3-yl]-maleinimide;
(+)-~-(iH-indol-3-yl)-3-[1-(~-methoxy-3-dimethylaminapropyl)-6-nitro-1H-indol-3-yl]-maleinirnide;
~w~_~a~~J
(+)-2-(1H-indol-8-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-nitro-1H-indol-3-yl]-maleinimide:
(+)-2-(iH-indol-3--yl)-3-(1-(2-methoxy-3-dimethylaminopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide:
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide:
(+)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methylthio-1H-indol -3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methylthio-iH-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-2H-indol-~-yl]-maleinimide;
(+)-2-(iH-indol-3-yl)-8-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
(+)-2-(1H-indol-3-yl)-3-[5,7-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-[4-acetylamino-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-acetylamina-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indal-3-yl)-maleinimide;
(-)-~-[7-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
(-)-2-[4-amino-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
~~r~~~, (-)-~-[5-amino-1-{2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-~-[6-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
(-)-2-[6-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-iFt-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
(--)-2-[7-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-~-{1H-indol-3-yl)-maleinimide;
(-)-~-[4-bromo-1-(2-meth~xy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl~--maleinimide;
(-)-2-[5-bromo-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-andol-3-yl)-maleinimide;
(-)-2-[6-bromo-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-bromo-1-{2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-chloro-1-(2-methoxy-3-dimethylami.nopropyl)-1H-indol-3-y1]-3-{1H-indal-3-yl)-maleinimide;
(-)~2-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(°)-2-[6-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-fluoro-1-(2-methoxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-fluoro-1-(~-methoxy-3~dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[4-hydroxy-1°(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[5-hydraxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[6-hydroxy-1-(2-me~thoxy-3~dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[7-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-i.ndol-3~y1]-3-(1H-indo3.-3-yl)-maleinimide;
(-)-2-[4-trifluoromethyl-1-(2-methoxy~3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-methoxy- 3-dimethylaminoprapyl)-1H-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
(-)-2-[6-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-~.H-indol-3-yl]-~-(1H-indol-~-yl)-maleinimide;
- 151 - ~ ebb ~ ~.~
(-)-2-[7-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[4-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-y1)-3-[5-methoxy-1-(~-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3 -[6-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[7-methoxy-1-(a-methoxy-s-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5,&-methylendioxy-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide:
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-~-dimethylaminopropyl)-4-methyl-1H-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-maleinimide:
(-)~2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methyl-2H-indol-~-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methyl-iH-indol-3-yl]-maleinimide;
(-)-2~(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-4-nitro-iH-indol-3-yl]-maleinimide;
1.52 - _~ a (-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-nitro-1H-indol-~-yl]-maleinimide;
(_)_2_(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-s-nitro-iH-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-nitro-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)--4-methylthio-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
(-)_2-(iH-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-methylthio-1H-indol-3-yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminoprapyl)-iH-indol-3-yl]-maleinimide;
(-)-2-(iH-indol-3-yl)-3-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol--3--yl]-maleinimide;
(-)-2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[4 -acetylamino-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(2-dimethylaminoethyl)-1I~I-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-~.-(2-dimethylaminoethyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 153 - ~~c.~~~.~
2-[?-acetylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[5-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
2-[6-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[?-benzyloxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-bromo-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-brama-1-(2-dimethylaminoethyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[?-bromo-1-(2~dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3 -y1)-maleinimide;
2-[5-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yI)-maleinimide;
2-[5-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(iH-indol-~-yl)-maleinimide;
2-[6-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoxomethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[5-trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7 -trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-~-[4-methoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-y1)-3-[6-methoacy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol~-3-yl)-3-[7-methoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-4,5-methylendioxy-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-5,6-methylendioacy-1H-indol-3-yl ] -maleinineide;
2-(1H-indol-3-yl)-3-[1-(Z-dimethylaminoethyl)-6,7-methylendio~cy-1H--indol-3-yl ] -maleinimide;
2-(1H-indol-3-yl)-3-[4-methyl-1-(2-dimethylaminoethyl)-~,H-indol-~-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-~.-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-;i-yl)-3-[6-methyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl)-maleinimide;
.2-(iH-indol-3-yl)-3-[1-(2-dimethylaminoethyl}-4-nitro-iH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[~.-(2-dimethylaminoethyl)-6-vitro-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[1-(2-dimethylaminoethyl)-7-vitro-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dime~hylaminoethyl}-4 -methylthio-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-5-methylthio-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[1-(2-dimethylaminoethyl)-6-methylthio-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3~yl}-3-[6,7-dimethoxy-1-(2-dimethylaminoethyl}-iH-indol-3-yl]-maleinimide;
2-[4-aaetylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
°
- 157 - ~~ e~.~~' 2-[5-acetylamino-1-(3-dimethylaminoprapyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-dimethylaminopropyl)~1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-amino-1-(3-dimethylaminopropyl)°1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-~.~(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinim$de;
2-[~-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~~bromo-1-(~-dimethylaminopropyl)-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3~-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
a-[7-bromo-1-(3-dimethylaminopropyl}-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[4 -chloro-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-y1)-maleinimide;
2-[5-chloro-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[6-ahloro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-dimethylaminopropyl}-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[6-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-hydroxy-1-(3-dimethylaminopropyl)-1H-indol-3-y1]-3-(iH-indol-3-yl)-maleinimide:
2-[5-h,ydroxy-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-hydroxy-1-(3-dimethylaminopropyl}-iH-indol-3-yl]-3-(1H-indol-3-yl)-malginimide:
2-[7-hydroxy-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-~-(1H-indol-3-y1)-maleinimide;
~~~~ t..
- 15 9 - .s. ei 2-[4-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[4-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-~-yl)-3-[7-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-y1)-maleinimide;
2-(1H-indol-3-yl)-~-[1-(3-dimethylaminopropyl)-4,5-methylendioxy-IH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-y1)-3-[1-(3-dimethylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methyl-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~-(1H-indol-3-yl)-3-[6-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~ ,~ Y~ ~~ ~ ,-160 - ~~.'a'.e>a:l~i 2-(1H-indol-3-yl)-3-[7-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
s-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-4-nitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-y1)-3-[1-(3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-6-vitro-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-7-vitro-iH-indol-~-yl]-maleinimide;
2--(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-~-methylthio-IH-indol-3-yI]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
2-(iH-indoi-3-yl)-3-[1-(3-dimethylaminopropyl)-6-methylthio-iH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-7-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)~-3-[6,7-dirnethoxy-1-(3-dimethylaminopropyl)-1H-lndol-3-yl]-maleinimide;
2-[4-aaetylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~~ - 161 - ~°r ~ .~ e.~ ~:~
2-[5-acetylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-methylaminopropyl)-1H-indol -3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-amine-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(~-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
Z°[5-benzyloxy-1-(~-methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleini~ide;
2-[6-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-bromo-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-a-yl)-maleinirnide;
2-[5-bromo-1-(3-methylaminopropyl)-iH-indol-~-yl]-3-(1H-indol-3-yl)-male.inimide;
- 162 - _~e~
2-[6-bromo-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl) -maleinimide;
2-[5-chloro-1-(3-methylaminopropyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-ahloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H~~indol-3-yl)-maleinimide;
2-[5-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide~
2-[7-fluoro-1-(3-methylaminopropyl)-1H-indol-~-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(~-methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-methylaminopropyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-hydroxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
_, 2-[7-hydroxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[6-trifluoromethyl-1-(3-methylaminopropyl}-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[4-methoxy-1-(3-methylaminopropyl)-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl}-3-[5-methoxy-1-(~-methylaminopropyl)-1H-indol -3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[6-methoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl}-3-[1-(3-methylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indal-3-yl)-3-[1-(3-methylaminopropyl)-6,7-methylendioxy-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[9~-methyl-1-(3-methylaminopropyl}-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-4-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-5-vitro-1H-indol-3-y1]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-6-vitro-1H-indol-3-yl]-.maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-7-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylarainopropyl)-4-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-5-methylthio-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-6-methylthio-1H-indol-3-y1]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-methylaminopropyl)-!-methylthio-1H-indol-3-yl]-maleinimide;
~-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
~-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
- 165 - ~.~s.~~~i~
2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-{3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[4-acetylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-{4-morpholino)propyl)~-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
z-[7-aaetylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[4-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-~3-(1H-indol-3-yl)-maleinimide;
2-[6-amino-1-(3-(4-morplnolino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[5-benzyloxy-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-benzyloxy-1-(3-(4-morpholino)propyl)-~1H-indol-a-yl]-3-(1H-indol-3-yl)-maleinimide;
~-[7-benzyloxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[4-bromo-1-(3-(4-morpholino)propyl)-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimide;
2-[6-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-(4-morpholino)propyl)-IH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-(~-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-ylj-maleinimide;
2-[7-chloro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-fluoro-1-(3-(4-morpholino)propyl)-IH-indol-3-yl]-3-(IH-indol-3-yl)-maleinimide;
2-[5-fluoro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2 -[6-fluoro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
-[7 -fluoro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydroxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
d :L 5:;7 d..: r 2-[5-hydroxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
a-[s-hydroxy-1-(a-(4-morpholino)propyl)-a.~a-indol-s-yl]-a-(iH-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoromethyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-(4-~orpholino)propyl)-1H-indol-~-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(iH-indol-3-yl)-3-[4-methoxy-1-(3-(4-morphalino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[6-methoxy-1-(3-(~-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methoxy-1-(3-(4°morpholino)propyl)-1Fi-indol-3-yl]-maleinimide;
2~(1H-indol-3-yl)-3-[4,5-methylendioxy~1-(3-(4-morpholino)prapyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[5,s-methylendioxy-1-(s-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide;
2-(iH-indal-3-yl)-3°[6,7-methylendioxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
' ~9' .d - ~ ~ ':.y~ ~ , ~-(1H-.indol-3-yl)-3-[4-methyl-1-(3-(&-morpholino)propyl)-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[5-methyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-inclol-3-yl)-3-[a-methyl-1-(3-(4-morpholino)propyl)-1H-indol-3-y1]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-4-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-5-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-6-vitro-2H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-7-vitro-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-3-[6-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
z-(1H-indol-3-yl)-3-(4,5-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
.... 169 - ~~ii~~.~a~.s''~~..~
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indal-3-yl]-maleinimide;
2-[4-acetylamino-1-(3-(2-nitroguanidina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-y1)-maleinimidet 2-[5-acetylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep 2-[6-acetylamino-~.-(3-(2-nitroguanidino)prapyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-(2-nitroguanidino)propyl)-2.H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[6-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-(2-nitroguanidino)progyl)-1H-indol-3-~yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[6-benzyloxy-1-(3-(2~nitraguanidino)prapyl)-1H-indol-3~yl]-~-(1H-indol-3-yl)-maleinimide;
a ~:~_~~~~~a 2-[7-benzyloacy-1-(3-(2-nitroguanidino)propyl}-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[5-bromo-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[6-bromo-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[7-bromo-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[4-chloro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide:
2-[5-chloro-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[6-chloro-1-(3-(2-nitrcguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-[7-chloro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[4-~luoro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
Z~[5-fluoro-1-(3-(2-nitroguanidino)propyl)-1H-indol~3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6~:~luoro-1-(3-(2-nitroguanidino)propyl}-iH-indol~3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[7-fluoro-1-(3-(2-nitroguanidino)prapyl)-iH-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[4-hydraxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-{iH-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[6-hydroxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-hydroxy-1-(3-(2-nitroguanidino)gropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-trifluoramethyl-1-(3-(2-nitraguanidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-(2-nitroguanidino)prapyl)-iH-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-trifluoromethyl-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-(2-nitroguanidino)prapyl)-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-(1H-indol-3-yl)-a-[4-methoxy-1-(3-(2-nitroguanidina)propyl)-iH-indol-3-yl]-maleinimide;
~-(1H-indal-3-yl)-3-[5-methoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3~yl)-3-[7-methaxy~1-(3-(2-nitroguanidino)prapyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-~-yl)-3-[4,5-methylendioxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
- 172 - ~:~.~~~)~J
2-(1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[6,7-methylendioxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methyl-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[5-methyl-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methyl-1-(3-(2--nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2'(1H-indol-3-yl)-3-[4-vitro-1-(3-(2°nitroguanidino)propyl}-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[5-vitro-1-(3-(2-nitroguanidino}propyl)-iH-indol-3-yl]-maleinimid~;
2-(1H-indol-3-yl)-3-[6-vitro-1-(3-(2-nitroguanidino}propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-vitro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[4-methylthio-1-(3-(2-nitroguanidino}propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-m~thylthio-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methylthio-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-~maleinimide;
2-(1H-indol-3-yl)-3-[7-methylthio-1-(3-(2-nitroguanidina)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[5,6-dimethoxy-I-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6,7-dimethoxy-1-(3-(2-nitroguanidino)progyl)-1H-indol-3-yl]-maleinimide;
2-[~-acetylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
2-[6-acetylamino-1-(3-(1.-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-acetylamino-I-(3-(1-piperidina)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-ma~leinimide;
2-[4-amino-I-(3-(1-piperidino)propyl)-2H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-(1-pigeridino}propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
Z-[6-amino-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-amino-1-(3-(1-piperidino)propyl)-1H-indol~3-yl]-3-(1H-indal-3-yl)-maleinimide;
2-[4-benzyloxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-lndol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-malei.nimide:
2-[6-benzyloxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-benzyloxy-y-(3-(1-piperidino)propyl)-iH-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide:
2-[4-bromo-1-(3-(1-piperidino)propyl)-1H~indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-bromo-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-bromo-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-~-(2H-indol-3-yl)-maleinimide;
2-[4-chloro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(2H-indol-3-yl)-maleinimide;
z-[5-ahloro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[6-chloro-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-chloro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-~-yl)-maleinimide;
2-[4-;Fluoro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl?-3-(1H-indol-3-yl)-maleinimide;
2-[5-:~luoro-1-(3-(~.-piperidino)p.ropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[6-fluoro-1-(3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-fluoro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[4-hydraxy-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[5-hydroxy-1-(3-(1-piperidina)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[6-hydroxy-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(1H-indol-3-yl}-maleinimide;
2-[7-hydroxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[~-trifluoromethyl-1-(3-(1-piperidino)propyl}-1H-indol-3-yl]-3-(lH~indol-3-yl)-maleinimide;
2-[5-trifluoromethyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(iH-indol-3-yl}-maleinimide;
2-[6-trifluoromethyl-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[7-trifluoromethyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(1H-indol-3-yI)-3-[4-methoxy-1-(3-(1-piperidino)propyl)-1H-indo:l-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidina)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl}-3-[6-methoxy-1-(3-(2-piperidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[7-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-y1)-3-[h,5-methylendioacy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(1-piperidino}propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[6,7-methylendioxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimic'ie;
2-(1H-indol-3-yl)-3-[4-methyl-1-(3-(1-piperidino)propyl)-~iH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[5-methyl-1~(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methyl-1-(3-(1°piperidino}propyl)-1H-indol-3-yl]-maleinimidet 2-(iH-indol-3-yl)-3-[7-methyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[~-nitro-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-nitro-1-(3-(1-piperidino)propyl)-1H-indol-~-yl]-maleinimide:
~-(1H-indol-3-yl)-3-[6-nitro-1-(3-(1-piperidina)propyl)-iH~
indol-3-yl]-maleinimide;
2-(1H-indal-3-yl}-3-[7-nitro-1-(3-(2-piperidino)propyl}-iH-indol-~-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-methylthio-1-(3-(1-piperidino)prapyl}-1H-indol-3-yl]-maleinimide;
-1~~-2-(1H-indol-3-yl)-3-[5-methylthio-1-(3-(1-piperidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-methylthio-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-methylthio-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[6,Z-dimethoxy-1-(3-(1-piperidino)propyl)-iH-indol-3-yl]-maleinimide:
bis-2,3-(4-aoetylamino-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-acetylamino-1H-indol-3-yl)-maleinimide:
bis-2,3-(6-acetylamino-1H-indol-3-yl)-maleinimide:
bis-2,3-(7-acetylamino-iH-indol-3-yl)-maleinimide;
bis-2,3-(4-amino-1H-indol-3-y1)-maleinimide;
bis-~,3-(5-amino-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-amino-1H-indol-3-yl)-maleinimide:
bis-2,3-(7-amino-1H-indol-3-yl)-maleinimide:
bis-~,3-(4-benzyloxy-iH-indol-3-yl)-maleinimide:
bis-2,3-(6-benzyloxy-1H-indol-3-yl)-maleinimide;
bis-2,3-('7-benzyloxy-1H-indol-3-yl)-maleinimide;
-1?8-bis-2,3-(4-bromo-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-bromo-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-bromo-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-chloro-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-chloro-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-chloro-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-fluoro-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-fluoro-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-fluoro-1H-indol-3-y1)-maleinimide;
bis-2,3-(~-hydroxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(f>-hydroxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(?-hydroxy-1H-indol-3-y1)-maleinimide;
bis-2,3-(4-trifluoromethyl-1H-indol-3-yl)--maleinimide;
bas-2,3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-trifluoromethyl-iH-indol-3-yl)-maleinimide;
bis-2,3-(?-trifluoromethyl-iH-indol-3-yl)-maleinimide;
bis-2,3-(4-methoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-methoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(?~methoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(6,7-methylendioxy-1H-indol-3-yl)-maleinimide:
bis-2,3-(4-methyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-methyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(7-methyl-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-vitro-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-vitro-1H-indol-3-yl)-maleinimide;
bis-2,3-(~-vitro-IH-indol-3-yl)-maleinimide;
bis-2,3-(7-vitro-1H-indol-3-yl)-maleinimide;
bis-2,3-(4-methylthio-1H-indol-3-yl)-maleinimide;
bis-2,3-(5-methylthio-1H-indol-3-yl)-maleinimide;
bis-2,3-(6-mathylthio-iH-indol-3-yl)-maleinimide;
bis-2,3-(7-methylthio-1H-indol-3-yl)-maleinimide;
bis-2,3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
bis-2,3-(6,7-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-ac~tylamino-1-(3-(amidinothio)propyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)~5-amino-1H-indol-3-yl]-3-(5-amina-1H-indol-3-y1)-malei.nimide;
2-[1-(3-(amidinothio)propyl)-5-benzyloxy-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
~~~ .1EL P.P~
2-[1-(3-(amidinothio}propyl)-5-bromo-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-chloro-1H-indol-3-yl]-3-(5-chloro-3H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-~-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)prapyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-2H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-4,5-methylendioxy-1H°indol-3-yl]--3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[2-(3-(amidinothio)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-malein:imide;
2-[1-(3-(amidinothio)propyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-5-methylthio-1H-indal-~-yl]-3-(5-methylthio-iH-indol-~-yl)-maleinimide;
z-[1-(3-(amidinothio)propyl)-4,5-dimethoxy-1H-indol~3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-~(3-(amidinothio)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-~.H-indol-3--yl)-maleinimide;
.S
2-[5-acetylamino-1-(2-aminoethyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(2-aminoethyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-benzyloxy-iH-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-(1-(2-aminoethyl)-5-bromo-1H-indol-3-yl]-~-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-chloro-IH-indol-3-yl]-3-(5-chloro-1H-indol-3-yl}-maleinimide;
2-(1-(2-aminoethyl}-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl}-maleinimide;
2-[1-(2-aminaethyl)~5-hydroxy-1H-indol-~-yl]-3-(5-hydroxy-iH-indol-3-yl}-maleinimide;
2-[1-(2-aminoethyl}-5-trifluoromethyl-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl}-maleinimide;
~-[1-(2-aminoethyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl}-maleinimide;
2-(1-(2-aminoethyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yI)-maleinimide;
2-[1-(2-aminoethyl)-5,6-methylendioxy-iH-indol-3-yl]-~-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
2-[1-(2-aminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide:
2-[5-acetylamino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide:
2-[5-amino-1-(3-aminopropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-benzyloxy-1H-indol-3-yl]-3-(5-benzyloxy_ 1H-indal-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-5-bromo-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-5-chloro-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-fluoro-1H°indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide:
2-[1-(3-aminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-malainimide;
2-[1-(3-aminopropyl)-5-rnethoxy-1H-indol-3-yl]-3-(5-methaxy-1FI-indol-3-y1)-maleinimide;
2-[1-(3-aminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3~(~,5-methylendioxy-1H-indol-3-yl)-maleinimide;
~~~ ~~e 2-[1-(3-aminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl}-maleinimide;
2-[1-(3-aminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-vitro-iH-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methyithio-1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
z-[~.-(3-aminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,s--dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(3-ethaxy-2-hydroxypropyl}-1H-indol-3~
yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(i)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-3.H-indol-3-yl)-maleinimide:
(~}-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-iH-indol-3-yl)-maleinimide:
(~)-2~[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-ohloro-1H-indol~3-yl)-maleinimide;
(t}~2-[1-(3-ethoxy-2-hydroxypropyl)-5~fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)~maleinimide;
(~)°2-[1-(3-ethoxy-2-hydroxypropyl)~5~hydroxy-1H~indol-3-yl]-3-(5-hydroxy-1H-indol~3-yl)-maleinimide;
(~j-2-[1-(3-ethoxy-~-hydraxypropyl)-5-trifluoromethyl-1H-indol-3-y1J-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxyprapyl)-5-methoxy-1H-indol-3-y1J-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(ø)-2-[I-(3-ethoxy-2-hydroxypropylj-4,5-methylendioxy-1H-indol-3-ylJ-8-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(~)-2-[7:-(3-ethoxy-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-ylJ-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-ethoxy-2-hydroxypropylj-5-methyl-1H-indol-3-y1J-3-(5-methyl-1H-indol-3-yl)-maleinimidei (~j-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-ylJ-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indol-3-y1J-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-y1J-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(~j-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-aoetylamino-1-(3-ethoxy-2-hydroxypropylj-1H-indol-3-y1J-3-(5-acetylamino-1H-indol-3-yl)-maleinimide~
(+)-2-[5-amino-1-(3-ethoacy-2-hydraxypropyl)-1H-indal-3-y1J-3-(5-amina-1H-indol-3-ylj-maleinimide;
(+)-2-[5-benzyloxy-1-(3-ethoxy-2-hydroxypropylj-1H-indol-3-y1J-3-(5-benzyloxy-1H-indol-3-ylj-maleinimide:
(+)-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-y1J-3-(5-bromo-1H-indol-3-yl)-maleinimide;
~a ~.t~j~e>~.9~i~
- is5 -(+)-2-[5-chloro-1-(3-ethoxy-2-hydroxypropyl}-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(+)-2-(1-(~-ethoxy-2-hydroxypropyl)-5-fluoro-1H-indal-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-hydroxy-iH-indol-3-yl]-3-(5-hydroxy-iH-indol-3-yl)-maleinimide;
(+}-2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yI]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxygropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(+}-2-[1-(3-ethoxy-2-hydroxyprapyl}-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(+)-2°[1-(3-ethoxy-2-hydroxypropyl)-5-methyl-iH-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl}-5-nitro-iH-indol-~-yl]-3-(5-nitro-1H-indol-3-yl}-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)~5,6-dimethoxy-1H-indol-3-y1]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
~'~~j.~~~~
(-)-2-[5-amino-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(3-ethoxy-Z-hydroxypropyl)-1H-indol-3-y1]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-iH-indol-3-yl)-maleinimide;
(-)°2-[5-chloro-1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-fluoro--1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(-)°2-[1-(3-ethoxy-~~hydroxypropyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(-)'2-[1-(3-ethoxy-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,G-methylendioxy-iH-indol-3-yl]-3-(5,ti-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1~(3-ethoxy-2-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3~
(5-methyl-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-vitro-1H-indol-3-y1]-3-(5-vitro-iH-indol-3-yl)-maleinimide;
(-)--2-[1-(3-ethoxy-2-hydroxyprapyl)-5-methylthio-1H-indal-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(-)_2-[1-(3-ethoxy-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;-2-[5-amino-1-(2-diethylaminoethyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(2-diethylam~.noethyl)-1H-indol-3-yl]-~-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(2-diethylaminoethyl)-1H-indol-3-yI]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(2~-diethylaminoethyl)-iH~indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-fluoro-1H-indol-3-yl]-3~(5-fluoro-1H-indol-3-yI)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-hydroxy-1H-indol-3-yl]--3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yI)-maleinimide;
2-[Z-(2-diethylaminoethyl)-5-methoxy-~.H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-G1-(2-diethylaminoethyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
-. 188 -2-[1-(2-diethylaminoethyl)-5-methyl-1H-indal-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-methylthio-1H°indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethyiaminoethyl)-4,5-dimethoxy-1FT-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl}-maleinimide;
(~)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yI]-3-(5-acetylamino-iH-indol-3-yl}-maleinimide;
(~}-2-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl}-maleinimide;
(~}-2-[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(~)-2-[5-chloro-1-(3-diethylamino-2-hydroxypropyl}-2H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(t)-2-[1-(3-diethylamino-2-hydrox~propyl)-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(t}-2-[1-(3-diethylamino-2-hydroxypropyl}-5-hydroxy-1H-indol-~-yl]-3-(5-hydroxy-1H-indol-3-yl}-maleinimide;
(t}-2-[1-(3-diethylamino-2-hydroxypropyl}-5-trifluoromethyl-1H-indol-3-~yl]-3-(5-trifluoromethyl-~.H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxyprapyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendiaxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxyprapyl)-5-methyl-iH-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-nitro-iH-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthia-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(~~,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)°2-[1-(3-diethylamina-2-hydroxyprapyl)-5,6-dimethaxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol°3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-amino-1-.(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-iH-indal-3=yl]-3-(5-benzyloxy-1H-~indol-3-y1)-maleinimide;
(+)-2-[5-broma-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-bromo-iH~-indol-3-yl)-maleinimide;
(+)-2-[5-chlora-1-(3-diethylamino-2-hydroxypropyl)-1H-~indol-3-yl]-3-~(5-chloro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamina-2-hydroxypropyl)-5-fluoro-iH-indol-3-yl]-3-(5-fluoro-iH-indol-3-y1)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-hydroxy-1H-i.ndol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-trifluoromethyl-iH-indol-3-yl]-3-(5-trifluoromethyl-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indnl-3-yl)-maleinimide;
(+)-2-[1,-(3-diethylamino-2-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-~-yl)-maleinimide;
(+)-~-[1-(3-diethylamino-2-hydroxypropyl)-5-vitro-2H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-z-hydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxyprrrpyl)-5,6--dimethoxy-iH-indal-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl)-maleinimide;
(-)-2-[5-aaetylamino-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-acetylamino-iH-indol-3-yl)-maleinimide;
(-)-~-[5-amino-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(3-diethylamino-2-hydroxypropyl)-iH-indol-3-yl]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
- 191 - ~~ ~~~'iJ
(-)-2-[5-bromo-1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-2H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-7l°(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(~-diethylamino-2-hydroxypropylj-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide:
(-j-2-[1-(3-diethylamino-z-hydroxypropyl)-5-hydroxy-2H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
(_)_~_[Z_(3_diethylamino-2-hydroxypropyl)-~k,5-methyiendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-~-hydroxypropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropylj-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleini.mide:
(-j-2-[1-(3~diethylamino-Z-hydroxypropyl)-5-methylthio-1'Ei-indol-~-yl]-3-(5-methylthio--1H-indol-3-yl)-maleinimide:
(-)~x-[1-(3-diethylamino-2-hydroxypropylj-4,5~dimethoxy-1H-3,ndol-3-yl]-3-(~,5-di.methoxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-{5-acetylamino-iH-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-diethylaminopropyl)-iH-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(5-chloro-1H-~indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-fluoro-iH-indol-3-yl]-3-(5-fluoro-iH-indol-3-ylj-maleinimide;
2-[1-(3-diethylaminopropyl)-5-hydroxy-iH-indol-3-yl]-3-(5-hydroxy-iH-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-trifluoromethyl-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-die.thylaminopropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4,5-methylendioxy-1H-indal-3--yI]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[~,-(3-diethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-iH-indol-3-yl)-maleinimide;
2-[1-(~-diethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide:
~1 ~I ~ 'J
! ' 2-[1-(3-diethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-4,5-dimethoxy-1H-indal-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indal-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-ethylaminoprapyl)-1H--indol-3-yl]-3-(5-acetylamino-1H-indoi-3-yl)-maleinimide;
2-[5-amino-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
2-[5-benzyloxy-1-(3-ethylaminopropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-ethylaminopropyl)-1H-indbl-3-y1]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
2-[5-chloro-1-(3-ethylaminoprapyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimidep 2-jl-(3-ethylaminoprapyl)-5-fluoro-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-hydroxy-1H-indol-3-yl]-3-(5-hydraxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminoprapyl)-5-trifluaromethyl-1H-indal-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(A.,S-methylendiaxy-1H-indol-3-yl)-maleinimide:
- 19~ -2-[1-(3-ethylaminopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-methyl-1H-indol-3-y1)-3-(5-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-vitro-iH-indol-3-yl]-3-(5-vitro-1H--indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl}-5-methylthio-1H-indol-3-yl)-3-(5-methylthio-1H-indol-3-yl}-maleinimide;
2-[1-(3-ethylaminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl)-3~(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamina-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-amino-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-amino-iH-indol-3-yl)-maleinimide;
(~)-2-(5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl)-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl}~-1H-indol-3-yl)-3-(5-bromo-1H-indol-3-yl}-maleinimide;
(t)-2-[5-chlora-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-y1)~~3-(5-chlora-1H-indol-3-yl}-maleinimide;
(t}-x-(5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(~)-2-(5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl)-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-~.-(2-hydroxy-3-dimethylaminoprapyl}-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(--1)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(1-)-2-[1-(2-hydroxy-3-dimethylaminoprogyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl}-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl}-maleinimide;
(~)--2-[1-(2-hydroxy-3-dimethylaminapropyl)-5-nitro-iH-indol-3-yl]-3-(5-nitro-1H~indol-3-yl}-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5-methylthio-1H-indol-3-yl]-3~(5-methylthio-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(~}-2-[1-(2-hydroxy-3 -dimethylaminopropyl}-5,6-dimethoxy-1H-indol-3-yl]~3-(5,6~dimethoxy-1H-indol-3-yl)-maleinimid~;
(+}-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl)-~1H-indol-3-yl]-3-(5-acetylamino-1H-indol -3-yl}-maleinimide;
(+)-~2~[5-amino~1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol~3-yl]-3~-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide:
(+)-2-[5-bromo-1-(~-hydroxy-3-d3.methylaminopropyl)~1H-indol-3-yl]-3-(5-bromo-1H-indol-3-y1)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-y1)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl}-iH-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl}-maleinimide;
(+)-2-[5-hydroxy-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(5-hydroxy-iH-indol-3-y1)-maleinim:ide;
(+)-2-[5-trifluoromethyl-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yI)-maleinimide;
(+}-2-[1-(2-hydroxy-3-dimethylaminapropyl)-5-methoxy-1H--indol-3-yl]-3-(5-methoxy-iH-indol-3-yl}-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H-indol--3-yl]-3-(4,5-methyl.endioxy-iH-indol-3-yl)-maleinimide;
(+}-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,~-methylendioxy-1H-indol-3-yl]-3~(5,6-methylendioxy-1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5-methyl-1H-indol-3-yl]-3-(5-methyl-iH-indol-3-y1)-maleinimide;
(+)~2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl}-5-methylthio-iH-indol- 3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(+}-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(4,5-dimethoxy-1H-indol°~-y~.)-maleinimide;
(+)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl}-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-dimethylaminopropyl}-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
- 197 - ~~G~~<.
(-)°~-[5-amino-1-(2-hydroxy-~-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydroxy-3-di'aethylaminopropyl)-iH-indol-3-yl]-3-(5-benzyloxy-iH-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(-)-2-[5-fluoro-1-(2-hydroxy-3-dimethylaminopropyl)-1H-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(-)-2-[5-hydraxy-1-(2-hydroxy-3-dimethylaminopropyl)-iH-indol-3-y1]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1-(2-hydraxy-3-dimethylaminapropyl)-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxx-3-dimethylaminapropyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(-)~2-[1-(2-hydroxy~3-dimethylaminoprapyl)-5-vitro-1H-indol-~-yl]-3-(5-vitro-1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-dimethylaminoprapyl)-5-methylthio-1H-indol -3-yl]-3-(5-methyLthio-iH-indol-3-yl)-maleinimide;
- 198 - ~j_~ ~J~~.
(-)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-4,5-dimethoxy-iH-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(°)-2-[1-(2-hydroxy-3-dimethylaminopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl)-maleinimide;
(~)-2-[5-aaetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-acetylamino-iH=indol-3-yl)°maleinimide;
(--1)-2-[5-amino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(5-amino-iH-indol-3-yl)-maleinimide:
(~)-2-[5-benzyloxy-1-(~-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide:
(t)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholina)propyl)-iH-indol-3-y1]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(ø)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-y1]-3-(5-chloro-iH-indol-3-yl)-maleinimide:
(~)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)prapyl)-iH-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(~)-2-[5-hydroxy-1-(2-hydroxy-3-(4-morphalino)propyl)-1H-indol-3-yl]-3-(5-hydroxy-1H-indol°3-yl)-maleinimide:
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide:
(i)-2-[1-(2-hydroxy-3-(9-morpholino)propyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl)-maleinimide;
(f)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-~,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide:
- 199 - ~~.~~.~i~~~c.
(~)-2-[1-(~-hydroxy-3-(4-morpholino)propyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-vitro-,iH-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide;
(~)-2-[l.-(2-hydroxy-3-(4-morpholino)propyl)~-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(~)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-dimethoxy-iH-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide:
(+)-2-[5--acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(+)-~-[5-amino-1-(2 -hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morphoiino)propyl)~iH-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-(~-morpholino)propyl)-iH-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol--3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(+)-2-[5-fluora-~.-(2-hydroxy-3-(4-morpholino)propyl)~1H-indol-3-yl]~3-(5~fluoro-1H-indol -3-yl)-maleinimide;
(+)~2-[5-hydroxy-~.~(2-hydroxy-3-(4 -morpholino)propyl)-iH-indol-3-yl]-3°(5-hydroxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-trifluoromethyl-~.-(2-hydroxy-3~(4-morphalino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-iH-indol-3-yl)-3-(5-methoxy-1H-indol-3-y1)-maleinimide;
(+)~2-[1-(2-hydroxy-3-(4-morpholino)propyl)-~,5-methylendioxy_ 1H-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide~
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)~-5,6-methylendioxy-1H-indol-3-yl)-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)~-5-methyl-iH-indol-3-yl]-a-(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-vitro-iH-indol-3-yI]-3°~(5-vitro-1H~-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio~1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholina)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(4-morpholino)progyl)-5,6-dimethaxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2-hydroxy-3-(~1-morpholino)propyl)-iH-indol-3-yll-3-(5-amino-1H-indol-a-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2-hydroxy-3-(4-morpholino)propyl)-iH-indol--3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-~.-(2-hydroxy-3-(4-morpholino)propyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
'~ ~. ~) ~ ~ 't 7 (-)-2-[5-fluoro-1-(2-hydroxy-3-(4-morpholino)propyl}-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-(4-morpholina)propyl)-1H-indol-3-yl]-~-(5-hydroxy-1H-indol-3-yl)-maleinim~.de~
(-)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(~-morpholina)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl}-maleinimidet (-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(4-morpholino}propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indo~.-3-yl)-maleinimide:
(°)-2-[1-(2-hydroxy-3-(4-morpholino)propyl}-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(-)-~-[1-(2-hydroxy-3-(4-morpholino)propyl)-4,5-dimethoxy-1H-indal-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3_(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3~y1]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(1)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-amino-1H-indal-3-yl)-maleinimide;
C~'~~~~_ (~)-2-[5-benzyloxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(~)°2-[5-bromo-l-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(1-)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(~)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-~-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimid~e;
(-~)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H--indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-{2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidina)propyl)-5,6-methylendioxy-1H-indol-3-y1]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methyl-~.H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(~,-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimid~;
(t)-~-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(t)-2-[1-(2-hydroxy-3-(2-piperidino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-a-(4,5-dlmethoxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydraxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-y1]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino}propyl}-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl}-maleinimide;
(+}-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-2-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-y1)-maleinimide;
(+)-2-[5-bromo-1-(2-hydroxy-3-(Z-piperidino}propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl}-maleinimide;
(+)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]d3-(5-hydroxy-1H-indol-3-yl}-maleinimide:
(+)-2-[5-trifluaromethyl-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H--indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(+)-2 -[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-methylendioxy-2H-indal-3-yl]-3-(4,5-methylendioxy-1FI-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methyl,-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-nitro-2H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(I-piperidino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5,f-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2-hydroxy-3-(1-piperidino)propyl)-2H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-~benzyloxy-z-{2-hydroxy-3-(1-piperidino)propyl)-2H-indol-3-yl]-3-(5-benzyloxy-1H-indol~3-yl)-maleinimide;
(-)-2-[5-bromo-1°(~-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[5-chloro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(-)-2-[5-fluoro-1-(2-hydroxy-3-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2-hydroxy-3-(1-pipmridino)propyl)-1H-~indol-3-yl]-3-{5-hydroxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-trifluoromethyl-1~(2-hydroxy-~-(1-piperidino)propyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-malsinimide;
(-)-2-(~.-(2-hydroxy-3-(1-piperidino)propyl)-5-methoxy-1H-indol-~-yl]-3-(5-methoxy-1H-indol-3-yl)-male].nimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-methoxy-1H-indol-3-yl]-3-(1.H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-~,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piper.idino)propyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-7.H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)~-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleini~nide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-y1)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-7.H-indol-3-yl)-maleinimide;
(°)-2-[1-(2-hydroxy-3-(~.-piperidino)propyl)-~,5-dimethoxy-1H-indol-3-yl]-3-(~4,5-dimethoxy-1H-indol-3-yl)-maleinimide:
(-)-2-[2-(2-hydroxy-3-(1-piperidino)propyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-l.H-indol-3-yl)-maleinimide;
(~)-2-[5-acetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-5-acetylarnino-1H-~indol-3-yl)-maleinim~.de:
(~)-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(~)-2-[5-benzyloxy-1-(2,3~dihydroxypropyl)~1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(t)-2-[5-bromo-~,-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-bromo-~.H-indol-3-yl)-malein3mide;
(t)-2-[5-chloro-1-(2,3-dihydroxypropyl)-2H-indol-3-yl]-3-(5-chlaro-1H-indol-3-yl)-maleinimide:
~~.~e~~J~
(~)-2-(5-fluoro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-fluoro-iH-indol-3-yl)-maleinimide;
(~)-2-[5-hydroxy-I-(2,3-dihydroxygropyl)-iH-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl)-maleinimide;
(~)-2-[5-trifluoromethyl-2-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl)-maleinimide;
(ø)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(~)-~-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-lI3-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-~,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yI)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-vitro-iH-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
(t)-2-[2-(2,3-dihydroxypropyl)-5,6-dimethoxy-iH-indal-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(+)-~-[5-aaetylamino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-aoetylamino-iH-indol-3-yl)-maleinimide;
(~-)-2-[5-amino-1-(2,3-dihydroxypropyl)-JlH-indol-3-yl]-3-(5-amino-iH-indol-3-yl)-maleinimide;
(+)-2-[5-benzyloxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(+)-2-[5-bromo-1-(2,3-dihydroxypropyl}-iH-indol-3-yl]-3-(5-bromo-1H-indol-3-yl)-maleinimide;
(+)-2-[5-chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-iH-indol-3-yl)-maleinimide;
(+)-2-[5-fluoro-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-fluoro-ZFi-indol-3-yl)-maleinimide;
(+)-2-[5-hydroxy-1-(2,3-dihydroxypropyl)-iH-indol-3-yl]-3-(5-hydroxy-1H-indol-3-yl}-maleinimide;
(+)-2-[5-trifluoromethyl-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-iH-indol-3-yl]-3-(5-methoxy-iH-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(~,5-methylendioxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5,6-methylendioxy-iH-indol-3-yl]-3°(5,6-methylendioxy-lI~-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3--(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-2-Z1-(2,3-dihydroxypropyl}-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H°-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide:
(+)-2-[1-(2,3-dihydroxypropyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-iH-indol-3-yl)-maleinimide;
.9 . a y E~
(+)-2-[1-(2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-y1]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-acetylamino-1-(2,3-dihydroxy~aropyl)-1H-indol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-amino-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-amino-1H-indol-3-yl)-maleinimide;
(-)-2-[5-benzyloxy-1-(2,3-dihydroxypropyl)-3.H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
(-)-2-[5-bromo-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3~(5-bromo-1H-indol-3-yl)-maleinimide;
(-)-2-[g_chloro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-chloro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-fluoro-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
(-)-2-[5-hydroxy-1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-hydroxy-iH-indol-3-yl)-maleinimide~
(-)-2-[5-trifluoromethyl-~.-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(5-trifluoromethyl-IH-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide~
(-)-2-[~.-(2,3-dihydroxyprapyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
a ~ ~ ~t~ vrn ',,~ ~:3 ,~J e~!
(-)-2-[1-(2,3-dihydroxypropyl)-5-nitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthia-1H-indol~3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxyprapyl)-4,5-dimethoxy-1H-indol-3-yl]-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[5-acetylamino-1-(3-hydroxypropyl)-1H-inclol-3-yl]-3-(5-acetylamino-1H-indol-3-yl)-maleinimide;
2-[5-amino-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-amine-1H-indol-3-yl)-maleinimide:
2-[5-benzyloxy-1-(3-hydraxypropyl)-1H-indol-3-yl]-3-(5-benzyloxy-1H-indol-3-yl)-maleinimide;
2-[5-bromo-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-broma-1H-indol-3-y1)-maleinimide;
2-[5-chloro-1-(3-hydroxypropyl)-1H-indal-3-yl]-3-(5-chlaro-1H-indal-3-yl)-maleinimide;
2-[5-fluoro-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-fluoro-1H-indol-3-yl)-maleinimide;
2-[5-hydraxy-1-(3-hydroxypropyl)-1H-indol-3-yl]-3-(5-hydroxy-1H-indal-3-yl)-maleinimide;
2-[5-trifluaromethyl-1-(3-hydroxypropyl)-5-trifluoramethyl-1H-indol-3-yl]-3-(5-trifluoramethyl-1H-indal-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-methaxy-1H-indol-3-yl]-3-(5-methaxy-1H-indol-3-yl)-maleinimide;
- zzo -z-[1-(3-hydroxypropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5,6-~nethylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide~
2-[1-(3-hydroxypropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-y1)-maleinimide;
2-[1-(3-hydroxypropyl)-5-vitro-1H-indol-3-y:l]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-methylthio-1H-indo:l.-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl}-4,5-dimethoxy-1H-indol-3-yl]-3-(~,5_ dimethoxy-2H-indol-3-yl)-maleinimidet 2-[1-(3-hydroxypropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-iH-indol-3-yl}-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
Z-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3 isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-chloro-1H-indol-3-y1)-3-[5-chloro-1-(;~-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide:
2-(5-~luoro-~.H-indol-3-yl)-3-[5-fluoro-1.-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
~
""t«~ n ~?~ .~~~'xJ
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide~
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-isothiocyanatopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
2-[1-(3-isothiocyanatopropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimidet 2-[1-(3-isothiocyanatopropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide:
2-[1-(3-isothiocyanatopropyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide:
2-[1-(3-isothiocyanatopropyl)-4,5-dimethoxy-1H-indol-3-yl)-3-(4,5-dimethoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5,6-dimethoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1H-indol-3-yl)-maleinimide;
(~)-2-(5-acetylamino-1H-indol-~-yl)-3-[5-acetylamino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(t)-2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(2-methoxy-3-d~,methylaminopropyl)-1H-indol-~-yl]-male~.nimide;
(t)-~-(5-benzyloxy-1H-indol-3-yl)-3~[5-benzyloxy-1-(2~methoxy-3-dimethylarninopropyl)-1H-indol-3-yl]-maleinimide:
- 2~2 -(~)-2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-~.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-(5-chloro-~.H-indol-3-yl)-~-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~j-2-(5-fluoro-2H-indol-3-yl)-3-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-2H-indol-3-yl]-maleinimide;
(~)-2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~j-2-(5-trifluoromethyl-1H-indol-3-y1)-3-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yI]-maleinimide;
(~)-2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-~.-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-[1--(2-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy-1H°indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-ylj-maleinimide;
(~j-2-[1-(2-methoxy-3-dimethylaminopropyl)-5,6-methylendioxy-1H-indol-~-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(z-methoxy-3-dimethylaminopropyl)-5-nitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1.H-indol-3-yl)-maleinimide;
(~)-2-(4,5-dimethoxy-1H-indol-3-yl)-~3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-11H-indol-3-yl]-maleinimide;
(t)-2-(5,6-dimethaxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminapropyl)-1H-indnl-3-yl]-maleinimide;
(+)-2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-maleinimide;
(+)-2-(5-amino-1H-indol.-3-yl)-3-[5-amino-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(5-benzyloxy-1H-indol-3-y1)-3-[5-benzyloxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol.-3-yl]-malei.nimide;
(+}-2-(5-bromo-1H-indol-3-yl}-3°[5-bromo-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-maleinimide;
(+)-2-(5-ahloro-1H-indol-3-yl)-3-[5-chloro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(5-fluoro-1H-inclol-3-yl)-3-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-(5-hydroxy-1H-indol-3-yl}-3-[5-hydroxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+}-2-(5-trifluoromethyl-1H-indol-3-yl)-~-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl}-1H-indol-3-yl]-maleinimide;
(+)-~-(5-methoxy--1H-indol-3-yl)-3-[5-methoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylaminopropyl)-4,5-methylendaoxy~
1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl}-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylaminopropyl}-5,6-methylend:ioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylamiisopropyl)-5-methyl-1H-indol-3-yl]-3-(5-methyl-1H-indol-3-yl)-maleinimide;
(+)-~-[1-(2-methoxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methylthio-iH-indol-3-yl)-~-(5-methylthio-1H-indol-3-yl)-malsinimide;
(+)-2-(4,5-dimethoxy-1H-indol-3-yl}-3-[4,5-dimethoxy-1-(z-methoxy-3-dimethylaminopropyl}-1H-indol-3-ylJ-maleinimide;
(+)°2-(5,6-dime~thoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2 -methoxy-3-dimethylaminopropyl)-iH-indol-3-ylJ-maleinimide;
(-}-2-(5-acetylamino-iH-indol-3-yl}-3-[5-acetylamino-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-}-z-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-y1J-maleinimide;
(-)-2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-1-(z-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl)-maleinimide;
(-)-2-(5-chloro-iH-indol-3-yl)-3-[5-chlaro-1-(2-methoxy-3-dimethylaminopropyl}-iH-indol-3-ylJ-maleinimide;
(~)-2-(5-fluoro-1H-indol-3~-yl)-3-[5-fluoro-1-(2-methoxy-3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
(-)-2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(z-methoxy-3-dimethylaminopropyl}-iH-indol-3-yIJ-maleinimide;
(-)-2-(5-trifluoromethyl-iH-indol-3-y1)-3-[5-trifluoromethyl-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(z-methoxy-3-dimethylaminopropyl)-1H-indol-3-ylJ-maloini,mide;
(-}--z-[1-(z-methoxy-3-dimethylaminopropyl)-4,5-methylendioxy_ 1H-indal-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
t;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5,c-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-methyl-1H-indol-3-yl]-~-(5-methyl-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-vitro-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-methoxy-3-dimethylaminopropyl)-5-m~thylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-y1)-maleinimide;
(-)-2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(-)-2-(5,6-dimethoxy-1H-indol-3-yl)-~-[5,6-dimethoxy-1-(2-methoxy-3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide:
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide:
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide:
2-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-~-yl)-3-[5-bromo-1-(2-dimethylaminoethyl)-1H-indol-3-yl)-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-[5-chlora-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(2 -dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
a a. ~
2-(5-tri~luoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-maleinimide;
2-[1-(2-dimethylaminoethyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(2-dimethylaminoethyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-[1-(2-dimethylaminoethyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-iH-indol-3-yl)-maleinimide;
2-[1-(2-dimethylaminoethyl)-5-methylthio-iH-indol-3-yl]-3-(5-methylthio-iH-indol-3-yl)-maleinimide;
2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethaxy-1-(2-dimethylaminoethyl)-iH-indol-3-yl]-maleinimide;
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(5-acetylamino-iH-indol-3-yl)-3-[5-acetylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~-(5-amino-iH-indol-3-yl)-3-[5-amino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-malein~.mide;
2-(5-benzyloxy-1H-indol-3-yl)-3-(5-benzyloxy-1-(3-dirnethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-~-yl)-3-[5-bromo-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
~a ~ ~i 2-(5-chloro-1H-indol-3-yl)-3-[5-chloro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(~-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl--1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-iH-indol-3-yl)-3-[5-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-ylJ-maleinimide;
2-[1-(3-dimethylaminopropyl)-4,5-methylendioxy-iH-indol-3-yl]-3-(4,5-methylendioxy-iH-indol-3-yl)-maleinimide;
2-[1-(3-dimethylaminopropyl)-5,6-methylendioxy-iH-indol-3-yl]-3-(5,6-methylendioxy-iH-indol-3-yl)-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-dimethylaminopropyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-dimethylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
2-(4,5-dimsthoxy-1H-indol-3-yl)-3-[4,8-dimethoxy-1-(3-dimethylaminopropyl)-iH-indol-3-y1]-maleinimide;
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-dimethylaminopropyl)-iH-indol-3-yl]-maleinimide;
2-(5-aoetylamino-iH-indol-3-yl)-~-[5-acetylamino~1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
~~~~.~~..~~~
2-(5-amino-1H-indol-3-yl}-3-[5-amino-1-(3-methylaminopropyl}-1H-indol-3-yl]-maleinimide;
2-(5-henzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-1-(3-methylaminopropyl}-1H-indol-3-yl]-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-[5-chloro-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3--methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-methylaminopropyl)-4,5-methylendioxy-1H-indol-3-yl]-3-(4,5-methylendioxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-methylaminapropyl)-5,6-methylendioxy-1H-indol-3-yl]-3-(5,6-methylendioxy-1H-indol-3-yl)-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-methylaminopropyl)-5-vitro-1H-indal-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-[1-(3-methylaminopropyl)-5-methylthio-1H-indol-3-yl]-3-(5-methylthio-1H-indol-3-yl)-maleinimide;
- zis -2-(4,5-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide:
2-(5,6-dimethoxy-iH-indol-3-yl}-3-[5,6-dimethoxy-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-~-[5-acetylamino-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-1H-indol-3-yl}-3-[5-bromo-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-chloro-iH-indol-3-yl)-3-[5-chloro-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide;
2-(5-hydroxy-iH-indol-3-yl)-3-[5-hydroxy-1-(3-(4-morvholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-(4-morpholino)propyl)-iH-indol-3-yl]-maleinimide:
Z-(4,5-methylendioxy-1H-indol-3-yl)-3-[4,5-methylendioxy-1-(3-(~t-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-methylendioxy-1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-(4-morpholinojpropyl)-iH-indol-3-yl]-maleinimide:
2-[1-(3-(4-morpholino)propyl)-5-vitro-1H-indol-3-yl]-3-(5-nitro-1H-indol-3-yl)-maleinimide;
2-(5-methylthio-iH-indol-3-yl)-3-[5-methylthio-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(4,5-dimethoxy-iH-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(~-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-ben~yloxy-iH-indol-3-yl)-3-[5-benzyloxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide:
2-(5-bromo-iH-indol-3-yl)-s-[5-bromo-1-(s-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-chloro-1H-indol-3-yl)-3-[5-chloro-1-(3-(2-nitroc~uuanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-fluoro-1H-indol-3-y1)-3-[5-fluoro-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
2~(5-hydroxy-1.H-indol-3-yl)-3-[5-hydroxy-1-(3-(~-nitracxuanidino)propyl)-iH-indol-3-yl]-maleinimide;
2-(5-trifluoromsthyl-iH-indol-3-yl)-3-[5-trifluoromethyl-1-(3-(~-nitroguanidino)prapyl)-1T~I-indol-3-yl]-malsinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3-(2-nitroguanidino)propyl)-iH-indol-3-yl]-maleinimide;
l'~,~1 ~ ~~~~:~
2-(4,5-methylendioxy-1H-indol-3-yl)-3-[4,5-methylendioxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-methylendioxy-1H-indol-3-yl)-3-[5,6-methylendioxy-1-(3-(2-nitroguanidino)propyl)-1H-indal-3-yl]-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-vitro-1H-indol-3-yl)-3-[5-vitro-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methylthio-1H-indol-3-yl)-3-[5-methylthio-1-(3-(2-nitroguanidino)propyl)-1H-indal-3-yl]-maleinimide;
2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(2-nitroguanidino)propyl)-1H-indoi-3-yl]-maleinimide;
2--(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-acetylamino-1H-indol-3-yl)-3-[5-acetylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-amino-1H-indol-3-yl)-3-[5-amino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3-(~.-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-bromo-iH-indol-3-yl)-3-[5-bramo-1-(3-(1-piperidino)prapyl)-1H-indol-3-yl]-maleinimide;
2-(5-~chlara-1H-indol-3-yl)-3-[5-chlora-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-floats-1H-indol-3-yl)-3-[5-floors-1-(3-(1-p3peridino)propyl)-1H-indol-3-yl]-maleinimide;
? .~ y; r,~1 r5, '3 ~~ ~ ~~ ~' x.~ ..~
2-(5-hydroxy-1H-indol-3-yl)-3-[5-hydroxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide:
2-(5-trifluoromethyl-1H-indol-3-yl)-3-[5-trifluoromethyl-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(4,5-methylendioxy-1H-indol-3-yl)-3-[4,5-methylendioxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-methylendioxy-1H-indal-3-yl)-3-[5,6-methylendioxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-(I-piperidino)progyl)-1H-indol-3-yl]-maleinimide;
2-(5-vitro-1H-indol-3-yl)-3-[5-vitro-1-(3-(1-piperidino)propyl)-1H-indoi-3-yl]-maleinimide;
2-(5-methylthio-1H-indol-3-yl)-3-[5-methylthio-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(4,5-dimethoxy-1H-indol-3-yl)-3-[4,5-dimethoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5,6-dimethoxy-1H-indol-3-yl)-3-[5,6-dimethoxy-1-(3-(1~-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-(amidinvthio)prapyl)-~t-dimethylamino-1H-indol-3-yl]-3--(~,H-indal-3-yl)-maleinimide;
2-[2-(3-(amidinathio)propyl)-5-dimethylamino-1H-indal-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-(amidinothio)propyl)-6-dimes,hylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
- 223 - G',a~.y~=~~~.'~
2-[1-(3-(amidinothio)propyl)-7-dimeth.ylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-6-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-aminoethyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H°
indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-6-dimethylamino-1H-indol-3-yI]-3-(1H-indol-3-yl)-maleinimide;
2-[Z-(3-aminopropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(3-ethoxy-2-hydroxypropyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
Z-[1-(3-ethoxy-2-hydroxypropyl)~5~dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2~[1~(3-ethoxy-2-hydroxypropyl)-6~dimethylamino-1H-indol-3-yl]-3-(1H~indol-3-yl)-maleinimide;
2~[1-(3-ethoxy-2-hydroxypropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
~_~'~:' 2-[1-(2-diethylaminoethyl)-4-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-6-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-7-dimethylamino-1H-indol-3-yl]-3-(iFi-indol-3-yl)-maleinimide;
(ø) 2-[1-(3-diethylamino-2-hydroxypropyl)-4-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(3-diethylam.ino-2-hydroxypropyl)-5-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(3-diethylamino-2-hydroxypropyl)-6~dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~~) 2-[1-(3-diethylamino-2-hydroxypropyl)-7-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-4~-dimethylamino-1H-indol-3-yl]-3-(1H-inddl-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
~[1-(3-ethylaminopropyl)-6-dimethylamino-iH-indol-3~-yl]~3-(iH-indol-3-yl)-maleinimide;
2-[1,-(3-ethylaminopropyl)-7-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(i) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-4-dimethylamino-1H-indol-3-yl]-3-(lEi-indol-3-yl)-maleinimide;
(~) 2-[~.-(2-hydroxy-3-dimethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(ø) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-6-dimethylamino-iH-indol-3-yl]-3-(iH-indol-3-yl)~maleinimide;
(~) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-7-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-4-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-6-dimethylamino-IH-indal-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(1-piperidino)propyl)-4-dimethy~.amino-iH-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
2-[1-(2-hydxoxy-3-(1-piperidino)propyl)-5-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(2-hydroxy-3-(1-piperidino)propyl)-6-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(1-piperidino)propyl)-7-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2,3-dihydroxypropyl)-4-dimethylamina-1H-indal-3-yl]-3-(iH-indol-3-yl)-maleinimid~;
(t) 2-[1-(2,3-dihydroxypropyl)-5-dimethylamino-iH-indol-3-yl]--3-(1H-indol-3-yl)-maleinimide;
fa (~) 2-[1-(2,3-dihydroxypropyl)-6-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2,3-dihydroxypropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidep 2-[1-(3-hydroxypropyl)-4-dimethylamino-iH-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-5-dimethylamino-1H-indol-3-y1]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-hydroxypropyl)-6-dimethylamino-1H-indol-3-yl]-3-(iH-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-7-dimethylamino-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimidet 2-(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-4-dimethylamino-iH-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-5-dimethylamino-1H-indol-3-yl]-maleinimide:
2-(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-6-dimethylamino-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[1-(3-isothiocyanatopropyl)-7-dimethylamino-1H-indol-3-yl]-maleinimidet (t) Z-(1H-indol-3-y7.)-3-[1-(2-methoxy-3-dimethylaminopropyl)-A-dimathylamino-iH-indol-3-yl]-maleinimide;
(i) 2-(iH-indol-3-yl)-3-[1-(2-metho~ty-3-dimethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-mal~inimide;
(~) Z~(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-6-dimethylamino-1H-indol-3-yl]-maleinimide;
(~) 2-(1H-indol-3-yl)-3-[1-(2-methoxy-3-dimethylaminopropyl)-7-dimethylamino-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(IH-indol-3-yl)-3-[7-dimethylamino-1-(2-dimethylaminoethyl)-IH-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[~-dimethylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-dimethylamino-Z-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-I-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[7-dimethylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-~-[4-dimethylamino-1-(3-methylaminopropyl)-1H-indol-3-yi]-maleinimide;
2-(1H-indol-3-yl)~3-[5-dimethylamino-1-(3-methylaminopropyl)~
1H-indol-3-yl]-maleinimide;
2-(7.H-indol-3-yl)-3-[G-dimethylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-~-[7-dimethylamino-1-(3-methylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-dimethylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-dimethylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[?-dimethylamino-1-(s-(~-morphoiino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[4-dimethylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
z-(1H-indol-s-yl)-3-[5-aimethylamino-z-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[6-dimethylamino-1-(3-(2-nitroguanidina)propyi)-ZH-indol-3-yl]-maleinimide;
2-(iH-indol-3-yl)-3-[?-dimethylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
a-(~H-indol-3-yl)-3-[4-dimethylamino-1-(3-(i-piperidino)propyl)-1H-indol-~-yl]-maleinimide;
2-(1H-indol-3-yl)-~-[5-dimethylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
Z-(1H-indol-3-yl)-3-[6-dimethylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-~-yl)-3-[?-dimethylamino-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(a-(amid.nothio)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
_.. ~:i~ ~ ' 2-[1-(2-aminoethyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide;
2-[1-(3-aminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
(~) 2-[1-(3-ethoxy-2-hydroxypropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
2-[1-(2-diethylaminoethyl)-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
(~) 2-[1-(3-diethylamino-2-hydroxypropyl)-5--dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
2-[1-(3-ethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-dimethylaminopropyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(4-morpholino)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2-hydroxy-3-(1-piperidino)propyl)-5-dimethylamino-1H-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide;
(~) 2-[1-(2,3-dihydroxypropyl)-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide:
2-[1-(3-hydroxypropyl)-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamina-1H-indol-3-yl)-maleinimide;
2-[1-(3-isothiocyanatopropyl)-5-dimethylamina-iH-indol-3-yl]-3-(5-dimethylamino-iH-indol-3-yl)-maleinimide;
(t) 2-[1-(2-Methoxy-3-dimethylaminopropyl)~-5-dimethylamino-iH-indol-3-yl]-3-(5-dimethylamino-1H-indol-3-yl)-maleinimide:
_.
- ~so -2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-(2-dimethylaminoethyl)-1H-indol-3-y1J-maleinimidet 2-{5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylaminn-1-{3-methylaminopropyl)-1H-indol-3-y1J-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-I-(3-(~-morpholino)propyl)-1H-indal-3-yl]-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-(3-(2-nitroguanidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-dimethylamino-1H-indol-3-yl)-3-[5-dimethylamino-1-{3-(1--piperidinu)propyl)-1H-indol-3-yl]-maleinimide.
Claims (8)
1. Bis-(1H-indol-3-yl)-maleinimide derivatives of the general formula I, which derivatives are selected from the group consisting of:
2-(1H-indol-3-yl)-3-(1-methyl-1H-indol-3-yl)-maleinimide 2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide 2-(5-hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)maleinimide 2-(5-benzyloxy-1H-indol-3-yl)-3-(1H-indol-3-yl)maleinimide 2,3-bis(5-methoxy-1H-indol-3-yl)maleinimide 2-(1H-indol-3-yl)-3-(5,6-methylendioxy-1H-indol-3-yl)maleinimide 2-(1H-indol-3-yl)-3-(5,6-dimethoxy-1H-indol-3-yl)maleinimide 2,3-bis-(5,6-methylendioxy-1H-indol-3-yl)maleinimide 2-(1FI-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)maleinimide 2-(5-benzyloxy-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide 2-[5-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleinimide 2-(5-methoxy-1H-indol-3-yl)-3-[5-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide (~)-2-(1H-indol-3-yl)-3-[1-(3-dimethylamino-2-methoxypropyl)-1H-indol-3-yl]maleinimide 2-(1H-indol-3-yl)-3-[5-(3-dimethylaminopropyloxy)-1H-indol-
3-yl]maleinimide 2,3-bis-(5-fluoro-1H-indol-3-yl)maleinimide 2-(5-fluoro-1H-indol-3-yl)-3-[5-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide 2,3-bis-(5-benzyloxy-1H-indol-3-yl)maleinimide 2-(5-benzyloxy-1H-indol-3-yl)-3-[5-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide 2-[5-benzyloxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1-methyl-1H-indol-3-yl)maleinimide 2,3-bis-(5-chloro-1H-indol-3-yl)maleinimide 2-(5-Chloro-1H-indol-3-yl)-3-[5-chloro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide 2,3-bis-(5-methyl-1H-indol-3-yl)maleinimide 2-(5-methyl-1H-indol-3-yl)-3-[5-methyl-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide 2,3-bis-(5-bromo-1H-indol-3-yl)maleinimide 2-(5-bromo-1H-indol-3-yl)-3-[5-bromo-1-(3-dimethylaminopropyl)-1H-indol-3-yl]maleinimide 2-(1H-indol-3-yl)-3-[1-(2-dimethylaminoethyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(6-methoxy-1H-indol-3-yl)-maleinimide:
2-[5-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-diethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide.
2-(5-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide; and (-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, and pharmaceutically acceptable salts thereof.
2. Process for the preparation of compounds of general formula I according to claim 1, R1 and R2 each being selected from the group consisting of hydrogen, methyl, 3-dimethylaminopropyl, 3-dimethylamino-2-methoxypropyl, 2-dimethylaminoethyl, 3-(1-piperidino)propyl, 3-(4-morpholino)propyl, 3-diethylaminopropyl, 3-diethylamino-2-hydroxypropyl, 2,3-dihydroxypropyl, 3-ethoxy-2-hydroxypropyl and 2-hydroxy-3-(1-piperidino)propyl, R4 and R9 each being selected from hydrogen and methoxy or R4 together with R5 forming a methylenedioxy group, or R9 together with R8 forming a methylenedioxy group, R5 and R8 each being selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, benzyloxy, fluorine, chlorine and bromine, the particular values of R1, R2, R4, R5, R8, and R9 being chosen to yield a compound listed in claim 1, wherein either A) a dibromomaleinimide of the general formula II, in which Z is a protective group, which can be split off, is reacted with an indole Grignard reagent of the general formula (A), 238~
in which R8 and R9 are as defined above with the exception of hydroxyl, and the product obtained of the general formula III, in which R1 is a hydrogen atom, is optionally alkylated at the indole nitrogen with an alkylation reagent of the general formula R1-X, in which, with the exception of hydrogen, R1 has the same meaning as in claim 1 but does not contain a functional group which would disturb the following reaction and X is a leaving group, a product being obtained of general formula III
but in which R1 is other than a hydrogen atom and subsequently the compound of general formula III is reacted with an indole Grignard reagent of the general formula (B), in which R4 and R5 are as defined above with the exception of hydroxyl, and subsequently optionally alkylated with an alkylation agent of the general formula R2-X, in which, with the exception of hydrogen, R2 has the same meaning as in claim 1 but does not contain a functional group which would disturb the following reaction and X has the above-given meaning, to give a compound of the general formula IV, whereafter the substituted imide group is converted into an unsubstituted imide group of the compound of general formula I;
or B) a compound of the general formula V, in which R8 and R9 have the above-given meanings and Y and Z
are protective groups, is reacted with an indole Grignard reagent of the general formula (B), in which R4 and R5 have the above-given meanings with the exception of hydroxyl, and if required subsequently alkylated with an alkylation agent of the general formula R2-X, in which R2 has the above-given meaning with the exception of hydrogen but does not contain a functional group which would disturb the following reaction and X has the above-given meaning, to give a compound of the general formula VI
whereafter the protected indole group is converted into a free indole group and the substituted imide group is converted into an unsubstituted imide group of a compound of general formula I, in which R1 is a hydrogen atom and R2 to R9 have the above-given meanings;
or C) a dibromomaleinimide of the general formula II, in which Z is a protective group, it is reacted with an excess of an indole Grignard reagent of the general formula (A), in which R8 and R9 have the above-given meanings with the exception of hydroxyl, and the product obtained of the general formula VII
in optionally alkylated on the indole nitrogen atom with an alkylation agent of the general formula R1-X, in which, with the exception of hydrogen, R1 has the above-given meaning but does not contain a functional group which would disturb the following reaction and X is a leaving group, to give a compound of the general formula VIII
in which R1 is other than a hydrogen atom, R2 is a hydrogen atom and R8 and R9 have the above-given meanings with the exception of hydroxyl, whereafter the substituted imide group is converted into an unsubstituted imide group of the compound of formula I;
followed, if required, by converting an obtained compound of formula (I) into a pharmaceutically acceptable salt thereof.
3. Process according to claim 2 wherein the leaving group X is chlorine or bromine.
2-(1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-diethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(-)-2-[1-(2,3-dihydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]-maleinimide:
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-ethoxy-2-hydroxypropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide:
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
(-)-2-[1-(3-diethylamino-2-hydroxypropyl)-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide:
2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-1H-indol-3-yl)-3-(5-methoxy-1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-methoxy-1H-indol-3-yl]-3-(6-methoxy-1H-indol-3-yl)-maleinimide:
2-[5-fluoro-1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide;
2-[1-(3-diethylaminopropyl)-6-methoxy-1H-indol-3-yl]-3-(5-methoxy-1H-indol-3-yl)-maleinimide.
2-(5-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-(5-fluoro-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide;
2-[1-(3-diethylaminopropyl)-5-fluoro-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(~)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(-)-2-[1-(2,3-dihydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide;
(+)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide; and (-)-2-[1-(3-ethoxy-2-hydroxypropyl)-5-methoxy-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleinimide, and pharmaceutically acceptable salts thereof.
2. Process for the preparation of compounds of general formula I according to claim 1, R1 and R2 each being selected from the group consisting of hydrogen, methyl, 3-dimethylaminopropyl, 3-dimethylamino-2-methoxypropyl, 2-dimethylaminoethyl, 3-(1-piperidino)propyl, 3-(4-morpholino)propyl, 3-diethylaminopropyl, 3-diethylamino-2-hydroxypropyl, 2,3-dihydroxypropyl, 3-ethoxy-2-hydroxypropyl and 2-hydroxy-3-(1-piperidino)propyl, R4 and R9 each being selected from hydrogen and methoxy or R4 together with R5 forming a methylenedioxy group, or R9 together with R8 forming a methylenedioxy group, R5 and R8 each being selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, benzyloxy, fluorine, chlorine and bromine, the particular values of R1, R2, R4, R5, R8, and R9 being chosen to yield a compound listed in claim 1, wherein either A) a dibromomaleinimide of the general formula II, in which Z is a protective group, which can be split off, is reacted with an indole Grignard reagent of the general formula (A), 238~
in which R8 and R9 are as defined above with the exception of hydroxyl, and the product obtained of the general formula III, in which R1 is a hydrogen atom, is optionally alkylated at the indole nitrogen with an alkylation reagent of the general formula R1-X, in which, with the exception of hydrogen, R1 has the same meaning as in claim 1 but does not contain a functional group which would disturb the following reaction and X is a leaving group, a product being obtained of general formula III
but in which R1 is other than a hydrogen atom and subsequently the compound of general formula III is reacted with an indole Grignard reagent of the general formula (B), in which R4 and R5 are as defined above with the exception of hydroxyl, and subsequently optionally alkylated with an alkylation agent of the general formula R2-X, in which, with the exception of hydrogen, R2 has the same meaning as in claim 1 but does not contain a functional group which would disturb the following reaction and X has the above-given meaning, to give a compound of the general formula IV, whereafter the substituted imide group is converted into an unsubstituted imide group of the compound of general formula I;
or B) a compound of the general formula V, in which R8 and R9 have the above-given meanings and Y and Z
are protective groups, is reacted with an indole Grignard reagent of the general formula (B), in which R4 and R5 have the above-given meanings with the exception of hydroxyl, and if required subsequently alkylated with an alkylation agent of the general formula R2-X, in which R2 has the above-given meaning with the exception of hydrogen but does not contain a functional group which would disturb the following reaction and X has the above-given meaning, to give a compound of the general formula VI
whereafter the protected indole group is converted into a free indole group and the substituted imide group is converted into an unsubstituted imide group of a compound of general formula I, in which R1 is a hydrogen atom and R2 to R9 have the above-given meanings;
or C) a dibromomaleinimide of the general formula II, in which Z is a protective group, it is reacted with an excess of an indole Grignard reagent of the general formula (A), in which R8 and R9 have the above-given meanings with the exception of hydroxyl, and the product obtained of the general formula VII
in optionally alkylated on the indole nitrogen atom with an alkylation agent of the general formula R1-X, in which, with the exception of hydrogen, R1 has the above-given meaning but does not contain a functional group which would disturb the following reaction and X is a leaving group, to give a compound of the general formula VIII
in which R1 is other than a hydrogen atom, R2 is a hydrogen atom and R8 and R9 have the above-given meanings with the exception of hydroxyl, whereafter the substituted imide group is converted into an unsubstituted imide group of the compound of formula I;
followed, if required, by converting an obtained compound of formula (I) into a pharmaceutically acceptable salt thereof.
3. Process according to claim 2 wherein the leaving group X is chlorine or bromine.
4. Pharmaceutical compositions containing at least one bis-(1H-indol-3-yl)-maleinimide derivative according to claim 1 together with a pharmaceutically acceptable diluent or carrier.
5. The use of a compound according to claim 1 for the preparation of a pharmaceutical composition for the treatment of heart and blood vessel diseases, inflammatory processes, allergies, cancer, degenerative damage of the central nervous system, diseases of the immune system and viral diseases.
6. The use of a compound according to claim 1 for the treatment of heart and blood vessel diseases, inflammatory processes, allergies, cancer, degenerative damage of the central nervous system, diseases of the immune system and viral diseases.
7. The use according to claim 5 wherein the heart and blood vessel diseases are thromboses, arteriosclerosis or hypertension.
8. The use according to claim 6 wherein the heart and blood vessel diseases are thromboses, arteriosclerosis or hypertension.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3914764.9 | 1989-05-05 | ||
| DE3914764A DE3914764A1 (en) | 1989-05-05 | 1989-05-05 | New bis(1H-indol-3-yl) maleinimide derivs. - are inhibitors of protein kinase C for treatment of cardiovascular, CNS and immune system disorders |
| DEP3942991.1 | 1989-12-27 | ||
| DE19893942991 DE3942991A1 (en) | 1989-12-27 | 1989-12-27 | New 2,3-bis:indolyl-maleimide derivs. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2015996A1 CA2015996A1 (en) | 1990-11-05 |
| CA2015996C true CA2015996C (en) | 2001-08-28 |
Family
ID=25880591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002015996A Expired - Fee Related CA2015996C (en) | 1989-05-05 | 1990-05-03 | Bis-(1h-indol-3-yl)-maleinimide derivatives and their use as pharmaceuticals |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0397060B1 (en) |
| JP (1) | JP2983248B2 (en) |
| KR (1) | KR900018080A (en) |
| AT (1) | ATE209202T1 (en) |
| AU (1) | AU634541B2 (en) |
| CA (1) | CA2015996C (en) |
| DE (1) | DE59010927D1 (en) |
| DK (1) | DK0397060T3 (en) |
| ES (1) | ES2169719T3 (en) |
| FI (1) | FI902251A7 (en) |
| HU (1) | HU207727B (en) |
| IL (1) | IL94274A0 (en) |
| NO (1) | NO179748C (en) |
| NZ (1) | NZ233560A (en) |
| PT (1) | PT93947B (en) |
| YU (1) | YU87990A (en) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ280738B6 (en) * | 1988-02-10 | 1996-04-17 | F. Hoffmann - La Roche And Co., Aktiengesellschaft | Substituted pyrroles, their use for preparing medicaments and medicaments based thereon |
| DE4005970A1 (en) * | 1990-02-26 | 1991-08-29 | Boehringer Mannheim Gmbh | NEW TRISUBSTITUTED MALEINIMIDES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| US5292747A (en) * | 1990-08-07 | 1994-03-08 | Hoffman-La Roche Inc. | Substituted pyrroles |
| CA2046801C (en) * | 1990-08-07 | 2002-02-26 | Peter D. Davis | Substituted pyrroles |
| GB9123396D0 (en) * | 1991-11-04 | 1991-12-18 | Hoffmann La Roche | A process for the manufacture of substituted maleimides |
| AU3761393A (en) * | 1992-03-20 | 1993-10-21 | Wellcome Foundation Limited, The | Indole derivatives with antiviral activity |
| DE4243321A1 (en) * | 1992-12-21 | 1994-06-23 | Goedecke Ag | Amino acid derivatives of heterocycles as PKC inhibitors |
| US5405864A (en) * | 1993-10-15 | 1995-04-11 | Syntex (U.S.A.) Inc. | Chemotherapeutic maleimides |
| US5541347A (en) * | 1993-12-07 | 1996-07-30 | Eli Lilly And Company | Synthesis of bisindolylmaleimides |
| US5723456A (en) * | 1993-12-07 | 1998-03-03 | Eli Lilly & Company | Therapeutic treatment for cardiovascular diseases |
| US5843935A (en) * | 1993-12-07 | 1998-12-01 | Eli Lilly And Company | Protein kinase C inhibitors |
| KR100340159B1 (en) * | 1993-12-07 | 2002-11-23 | 일라이 릴리 앤드 캄파니 | Protein Kinase C Inhibitors |
| BR9404830A (en) * | 1993-12-07 | 1995-08-08 | Lilly Co Eli | Compound and process for its preparation |
| US5624949A (en) * | 1993-12-07 | 1997-04-29 | Eli Lilly And Company | Protein kinase C inhibitors |
| EP1449529B1 (en) * | 1993-12-23 | 2010-01-27 | Eli Lilly And Company | Protein Kinase C Inhibitors |
| ES2230433T3 (en) * | 1994-05-09 | 2005-05-01 | Banyu Pharmaceutical Co., Ltd. | PROCEDURES FOR THE PREPARATION OF INDOLOPIRROLOCARBAZOL DERIVATIVES. |
| US5481003A (en) * | 1994-06-22 | 1996-01-02 | Eli Lilly And Company | Protein kinase C inhibitors |
| US5491242A (en) * | 1994-06-22 | 1996-02-13 | Eli Lilly And Company | Protein kinase C inhibitors |
| US5559228A (en) * | 1995-03-30 | 1996-09-24 | Eli Lilly And Company | Synthesis of bisindolylmaleimides |
| CA2237401C (en) * | 1995-11-20 | 2003-10-21 | Eli Lilly And Company | Novel intermediates and their use to prepare n,n'-bridged bisindolylmaleimides |
| PE91598A1 (en) * | 1996-07-29 | 1998-12-24 | Hoffmann La Roche | SUBSTITUTED PYRROLES |
| PE91698A1 (en) * | 1996-07-29 | 1998-12-24 | Hoffmann La Roche | SUBSTITUTED PYRROLES |
| PE91498A1 (en) * | 1996-07-29 | 1998-12-22 | Hoffmann La Roche | SUBSTITUTED PYRROLES |
| SE9603283D0 (en) * | 1996-09-10 | 1996-09-10 | Astra Ab | New compounds |
| JP2001503414A (en) * | 1996-10-31 | 2001-03-13 | ハーバー ブランチ オーシャノグラフィック インスティテューション インク． | Antineural inflammatory compounds and compositions and methods of use |
| AU2548699A (en) * | 1998-02-23 | 1999-09-06 | Rei Asakai | Cell death inhibitors |
| JP2002520315A (en) | 1998-07-08 | 2002-07-09 | ハーバー ブランチ オーシャノグラフィック インスティテューション インク． | Bisindole derivatives and their use as anti-inflammatory agents |
| EP1152002A4 (en) | 1999-02-09 | 2002-04-17 | Sagami Chem Res | PYRROLE DERIVATIVES AND CELL DEATH INHIBITORS |
| US6281356B1 (en) * | 1999-12-22 | 2001-08-28 | Hoffmann-La Roche Inc. | Substituted pyrroles |
| CA2308994A1 (en) * | 2000-05-19 | 2001-11-19 | Aegera Therapeutics Inc. | Neuroprotective compounds |
| US7129250B2 (en) | 2000-05-19 | 2006-10-31 | Aegera Therapeutics Inc. | Neuroprotective and anti-proliferative compounds |
| DE10109280A1 (en) * | 2001-02-26 | 2002-09-05 | Peter Mayser | Indole derivatives with inhibitory effects on protein kinases |
| TW201041580A (en) | 2001-09-27 | 2010-12-01 | Alcon Inc | Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma |
| PT1441737E (en) | 2001-10-30 | 2006-12-29 | Dana Farber Cancer Inst Inc | Staurosporine derivatives as inhibitors of flt3 receptor tyrosine kinase activity |
| CA2393720C (en) | 2002-07-12 | 2010-09-14 | Eli Lilly And Company | Crystalline 2,5-dione-3-(1-methyl-1h-indol-3-yl)-4-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1h-indol-3-yl]-1h-pyrrole mono-hydrochloride |
| JPWO2004091663A1 (en) * | 2003-04-18 | 2006-07-06 | 協和醗酵工業株式会社 | Nerve regeneration drug |
| RS51826B (en) | 2005-02-09 | 2012-02-29 | Arqule Inc. | MALEIMID DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND THE PROCESS OF CANCER TREATMENT |
| CA2690799C (en) | 2007-06-22 | 2015-06-16 | Arqule, Inc. | Pyrrolidinone, pyrrolidine-2,5-dione, pyrrolidine and thiosuccinimide derivatives, compositions and methods for treatment of cancer |
| CA2690782C (en) | 2007-06-22 | 2016-02-02 | Arqule, Inc. | Compositions and methods for treatment of cancer |
| CN101801937A (en) | 2007-06-22 | 2010-08-11 | 艾科尔公司 | Quinazolinone compounds and methods of use thereof |
| US8193235B2 (en) * | 2009-06-12 | 2012-06-05 | University Of Kansas | Compositions and methods for establishing and maintaining stem cells in an undifferentiated state |
| JP2017524739A (en) | 2014-07-17 | 2017-08-31 | アンセルムＩｎｓｅｒｍ | Method for treating neuromuscular junction related diseases |
| WO2016207366A1 (en) | 2015-06-26 | 2016-12-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of viral infections |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4785085A (en) * | 1986-11-21 | 1988-11-15 | Bristol-Myers Company | Rebeccamycin analogs |
| CZ280738B6 (en) * | 1988-02-10 | 1996-04-17 | F. Hoffmann - La Roche And Co., Aktiengesellschaft | Substituted pyrroles, their use for preparing medicaments and medicaments based thereon |
-
1990
- 1990-05-03 CA CA002015996A patent/CA2015996C/en not_active Expired - Fee Related
- 1990-05-03 PT PT93947A patent/PT93947B/en active IP Right Grant
- 1990-05-03 IL IL9094274A patent/IL94274A0/en unknown
- 1990-05-04 EP EP90108468A patent/EP0397060B1/en not_active Expired - Lifetime
- 1990-05-04 HU HU902681A patent/HU207727B/en not_active IP Right Cessation
- 1990-05-04 FI FI902251A patent/FI902251A7/en not_active Application Discontinuation
- 1990-05-04 AT AT90108468T patent/ATE209202T1/en not_active IP Right Cessation
- 1990-05-04 ES ES90108468T patent/ES2169719T3/en not_active Expired - Lifetime
- 1990-05-04 NO NO901989A patent/NO179748C/en unknown
- 1990-05-04 NZ NZ233560A patent/NZ233560A/en unknown
- 1990-05-04 AU AU54666/90A patent/AU634541B2/en not_active Ceased
- 1990-05-04 KR KR1019900006359A patent/KR900018080A/en not_active Withdrawn
- 1990-05-04 YU YU87990A patent/YU87990A/en unknown
- 1990-05-04 DE DE59010927T patent/DE59010927D1/en not_active Expired - Fee Related
- 1990-05-04 DK DK90108468T patent/DK0397060T3/en active
- 1990-05-07 JP JP2115916A patent/JP2983248B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO901989L (en) | 1990-11-06 |
| FI902251A7 (en) | 1990-11-06 |
| IL94274A0 (en) | 1991-03-10 |
| NO179748C (en) | 1996-12-11 |
| HUT53902A (en) | 1990-12-28 |
| EP0397060A2 (en) | 1990-11-14 |
| DK0397060T3 (en) | 2002-05-21 |
| EP0397060A3 (en) | 1992-01-02 |
| HU902681D0 (en) | 1990-09-28 |
| AU5466690A (en) | 1990-11-08 |
| NO179748B (en) | 1996-09-02 |
| PT93947A (en) | 1991-01-08 |
| NZ233560A (en) | 1992-01-29 |
| AU634541B2 (en) | 1993-02-25 |
| PT93947B (en) | 1996-11-29 |
| JP2983248B2 (en) | 1999-11-29 |
| ATE209202T1 (en) | 2001-12-15 |
| YU87990A (en) | 1992-07-20 |
| FI902251A0 (en) | 1990-05-04 |
| ES2169719T3 (en) | 2002-07-16 |
| JPH02306974A (en) | 1990-12-20 |
| HU207727B (en) | 1993-05-28 |
| CA2015996A1 (en) | 1990-11-05 |
| NO901989D0 (en) | 1990-05-04 |
| KR900018080A (en) | 1990-12-20 |
| DE59010927D1 (en) | 2002-01-03 |
| EP0397060B1 (en) | 2001-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5380746A (en) | Bis-(1H-indol-3-YL)-maleinimide derivatives, processes for the preparation thereof and pharmaceutical compositions containing them | |
| JP2983248B2 (en) | Maleimide derivatives and their use as medicaments | |
| JP2638752B2 (en) | 1-aminoethylindole derivative | |
| JPH0730071B2 (en) | Pyrrole | |
| EP0464558B1 (en) | Antimigraine alkoxypyrimidine derivatives | |
| RU2146256C1 (en) | DERIVATIVES OF AZOLE AND PHARMACEUTICAL COMPOSITION BASED ON THEREOF ELICITING ACTIVITY WITH RESPECT TO SEROTONIN 5-HT1Dα- | |
| JPH0741475A (en) | 3-Arylcarbonyl-1H-indole useful as a drug | |
| PT86188B (en) | PROCESS FOR THE PREPARATION OF REBECAMYCIN ANALOGS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM | |
| JP3157179B2 (en) | 3-Arylcarbonyl-1-aminoalkyl-1H-indole-containing anti-glaucoma composition | |
| HUP0002843A2 (en) | New betha-carboline compounds, a process for their preparation and pharmaceutical compositions containing them | |
| EP1244652B1 (en) | 2-(1h-indol-3-yl)-2-oxo-acetamides with antitumor activity | |
| DD297970A5 (en) | PROCESS FOR THE PREPARATION OF BE1- (1H-INDOL-3-YL) -maleimide-DERIVATIVES AND THEIR USE | |
| EP1556382A1 (en) | 3-phenyl substituted pyridoindolone, preparation and therapeutic use thereof | |
| Aoki et al. | Convenient synthetic method for 3-(3-substituted indol-2-yl) quinoxalin-2-ones as VEGF inhibitor | |
| AU673098B2 (en) | Antimigraine cyclobutenedione derivatives of indolylalkyl-pyridinyl and pyrimidinylpiperazines | |
| EP0785933B1 (en) | Indole derivatives as 5ht1-like agonists | |
| TW200301116A (en) | Isochroman compounds | |
| JP2003506376A (en) | 1,2-dihydro-1-oxo-pyrazino [1,2-a] indole derivatives | |
| Fattah et al. | Recent Advances in the Synthesis of Naratriptan: An Anti-Migraine Drug | |
| KR0139913B1 (en) | Substituted pyrrole, preparation method thereof and pharmaceutical containing same | |
| IE83486B1 (en) | Maleinimide derivatives and their use as medicaments | |
| DE3942991A1 (en) | New 2,3-bis:indolyl-maleimide derivs. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |