RU2814103C1 - New compound, method of its preparation and use - Google Patents

Abstract

FIELD: pharmaceuticals.

SUBSTANCE: invention relates to a compound that inhibits Pin1 (peptidyl-prolyl-cis/trans isomerase interacting with NIMA 1), or a pharmaceutically acceptable salt thereof, a method of producing the said compound, a pharmaceutical composition containing as an active ingredient a compound that inhibits Pin1, and its use for the prevention or treatment of malignancy.

EFFECT: obtaining a new compound and a method of its preparation.

18 cl, 5 tbl, 185 ex

Description

Field of technology

The present invention relates to a pharmaceutical composition for the prevention or treatment of malignancy, inflammatory disease or metabolic disease, in particular to a pharmaceutical composition containing as an active ingredient a compound that inhibits Pin1 (peptidyl-prolyl cis-trans isomerase interacting with 1) for prevention or treatment of malignancy, inflammatory disease or metabolic disease.

BACKGROUND OF THE INVENTION

Pin1 (peptidyl-prolyl cis-trans isomerase interacting with 1), a prolyl isomerase, is an enzyme that catalyzes the cis/trans isomerization of the amide residue of proline by binding to a phosphorylated Ser/Thr-Pro site (Lu, et al. Science 1999, 283(5406):1325-8). During intracellular signaling, serine (Ser), threonine (Thr), and tyrosine (Tyr) residues of proteins are phosphorylated. Following this phosphorylation, Pin1 alters the structure of various proteins through cis/trans isomerization of the amide of the proline residue, allowing these proteins to begin performing their functions in the cell.

Based on research to date, the Pin1 enzyme is known to be involved in the initiation and progression of inflammatory diseases, metabolic disorders, and malignancy. In particular, the Pin1 enzyme has been reported to activate 56 oncogenes involved in tumorigenesis, such as beta-catenin, AKT, AR, CyclinD1, Plk, NF-kB, Stat3, Myc, c-Jun, c-Fos, c-Myb, Raf-1, HIF-1, Nanog, Notch1, Oct4, etc., and inhibits the activity of 26 tumor suppressor genes such as ATR, Bax, Btk, FADD, Fbw7, PML, etc., thereby inducing cancer metastasis and cancer angiogenesis in the general mechanism of cancer development. Therefore, a number of studies are being conducted on the Pin1 protein as a target for the development of cancer diagnostic reagents, prognostic factors and useful new anticancer agents (Nature reviews Cancer 2016, 16:463-478; Cell Death and Disease 2018, 9:883).

As reported in a study of surgically excised specimens, it is known that Pin1 is highly expressed in various types of cancer, such as colon cancer, cervical cancer, breast cancer, lung cancer, pancreatic cancer, gastric cancer, liver cancer, etc. .d. In fact, transgenic mice overexpressing Pin1 have been reported to exhibit a tumorigenic phenotype. In addition, it is known that mitotic arrest and apoptosis can be induced and cancer stem cell properties can be suppressed in Pin1 knockout cancer cells using a specific inhibitor or siRNA. In particular, the Pin1 enzyme functions to induce self-renewal, metastasis, and tumorigenesis of breast cancer stem cells.

When Pin1 is overexpressed, human mammary epithelial cells differentiate into pseudostem cells and a transition from epithelium to mesenchyme occurs. In other words, when cancer cells grow invasively and metastasize to break adhesion to surrounding cells and move through blood or lymphatic vessels, the communication between cells is weakened, the skeleton of the cells is changed and motility is acquired. The Pin1 enzyme is known as an important factor in stem cell self-renewal, maintaining the stability of Nanog, Oct4 and Myc proteins.

Although Pin1 is involved in many mechanisms in vivo, as described above, Pin1 knockout mice are known to grow well without major problems. Therefore, Pin1 inhibition is not expected to have significant effects in humans. However, while there are reports that Pin1 may help in the brain in treating Alzheimer's disease, there are reports that it acts in the opposite way in Parkinson's disease, and there are many parts that have not yet been identified. In conclusion, Pin1 plays a very important role in malignancy in general, and its inhibition in areas other than the brain is very beneficial for effective and safe cancer treatment.

In addition, it has been reported that when Pin1 is inhibited or Pin1 gene expression is suppressed, the production of prostaglandin E2 and nitric oxide stimulated by lipopolysaccharide (LPS) and nicotine is attenuated, and the expression of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) is also reported to be attenuated. are weakened, resulting in an anti-inflammatory effect (Journal of Dental Research, 2015, 94(2):371-380). It is well known that when Pin1 is attached to CRTC2, the production of the CBP-CRTC2-CREB complex, which promotes gluconeogenesis, is inhibited, so that CRTC2 may be regulated according to the expression level of Pin1 and thus may be involved in the regulation of glucose metabolism (J. Biol Chem, 2010, 285(43):33018-27). Therefore, drugs that affect the expression or activity of Pin1 can be used as therapeutic agents for an inflammatory disease or metabolic disease such as diabetes.

Thus, the inventors of the present invention performed pharmaceutical chemical synthesis and biological and pharmacological evaluation of the synthesized compounds to discover compounds that inhibit Pin1 activity. Due to this, the inventors of the present invention discovered compounds exhibiting excellent anticancer effect by potently inhibiting Pin1 and developed the present invention. In addition, it is believed that the compounds of the present invention can be used as therapeutic agents for the treatment of diseases based on the role of Pin1 in inflammatory and metabolic diseases.

Description of the invention

Technical problem

The aim of the present invention is to provide a new compound, an isomer thereof or a pharmaceutically acceptable salt thereof, which inhibits Pin1 (NIMA 1-interacting peptidyl-prolyl cis/trans isomerase).

Another object of the present invention is to provide a method for preparing the compound.

Another object of the present invention is to provide a pharmaceutical composition containing a compound, an isomer thereof or a pharmaceutically acceptable salt thereof as an active ingredient, for the prevention or treatment of a malignancy, an inflammatory disease or a metabolic disease.

Another object of the present invention is to provide a functional health product composition containing a compound, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient, for the prevention or amelioration of a malignancy, an inflammatory disease, or a metabolic disease.

Technical solution

To achieve the above objects, in one aspect of the present invention, the present invention provides a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof:

[Formula 1]

(In formula 1

Ar is a 6-10 membered aryl or 5-10 membered heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O;

R ¹ and R ² are independently hydrogen, halogen or 5-8 membered heterocycloalkyl C _1-5 alkoxy containing at least one N;

R ³ represents hydrogen, halogen, unsubstituted or substituted straight or branched C _1-8 alkoxy, unsubstituted or substituted straight or branched C _1-8 alkyl, NR ^a1 R ^a2 or OR ^a3 , where R ^a1 , R ^a2 and R ^a3 , independently, are hydrogen, unsubstituted or substituted straight or branched C _1-8 alkyl, unsubstituted or substituted phenyl or 5-8 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O,

wherein substituted alkoxy, substituted alkyl, substituted phenyl and substituted heteroaryl are, independently, substituted with one or more substituents selected from the group consisting of 4-8 membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 4-8 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, NR ^b1 R ^b2 , 3-6 membered cycloalkyl, halogen, hydroxy and sulfonyl, or substituted alkoxy and substituted alkyl can be further substituted to form a 3-6 membered cycloalkyl with each independently substituted carbon atom,

substituted heterocycloalkyl and substituted heteroaryl are substituted with one or more substituents selected from the group consisting of straight or branched C _1-5 alkyl, unsubstituted or substituted by one or more halogens, straight or branched C _1-5 alkylcarbonyl, NR ^b1 R ^b2 , halogen, hydroxy and oxo,

R ^b1 and R ^b2 are independently hydrogen or straight or branched C _1-6 alkyl;

L ¹ represents or , where R ^c represents hydrogen or L ² and forms a 5-8 membered heterocycloalkylene containing N, together with the nitrogen atom to which they are attached;

L ² represents a single bond, straight or branched C _1-8 alkylene, C _3-8 cycloalkylene or phenylene, unsubstituted or substituted with one hydroxy and oxo;

Z represents unsubstituted or substituted C _6-10 aryl, C _3-8 cycloalkyl, unsubstituted or fused with a 5-9 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, 4-8-membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 5-9-membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group including N, S and O, or 5-9 membered unsubstituted or substituted heteroaryl C _1-5 alkyl containing one or more heteroatoms selected from the group consisting of N, S and O,

substituted aryl is substituted with halogen, phenyl, carboxy, 4-8 membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, or straight or branched C1-8 alkoxycarbonyl,

wherein substituted heterocycloalkyl, substituted heteroaryl and substituted heteroarylalkyl are, independently, substituted with one or more substituents selected from the group consisting of straight or branched _C1-5 alkyl, straight or branched _C1-8 alkoxy, phenyl, benzyl, halogen, hydroxy or oxo.)

In another aspect of the present invention, a method for producing a compound represented by Formula 1 includes the step of producing a compound represented by Formula 1 by reacting a compound represented by Formula 2 with a compound represented by Formula 3, as shown in Reaction Scheme 1 below:

[Reaction Scheme 1]

(In the reaction scheme 1 Ar, R ¹ , R ² , R ³ , L ¹ , L ² and Z have the meanings defined in formula 1 of paragraph 1 of the claims,

J ¹ represents chlorosulfone or carboxy; And

J ² is an amine or piperidine.)

In another aspect of the present invention, the present invention relates to a pharmaceutical composition containing, as an active ingredient, a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof, for the prevention or treatment of cancer, an inflammatory disease, or a metabolic disease.

In another aspect of the present invention, the present invention relates to a functional health product composition containing, as an active ingredient, a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof, for the prevention or amelioration of cancer, an inflammatory disease, or a metabolic disease.

In another aspect of the present invention, the present invention relates to a method for preventing or treating a malignancy, inflammatory disease or metabolic disease, comprising the step of administering to a subject in need thereof a pharmaceutical composition or a functional health product composition containing as an active ingredient a compound represented by Formula 1, or a pharmaceutically acceptable salt thereof.

In another aspect of the present invention, the present invention relates to the use of a pharmaceutical composition or a functional health product composition containing as an active ingredient a compound represented by Formula 1, or a pharmaceutically acceptable salt thereof, for the prevention or treatment of a malignancy, an inflammatory disease or a metabolic disease.

Positive effects of the invention

Since the novel compound of the present invention exhibits excellent Pin1 inhibitory activity, a pharmaceutical composition containing the compound as an active ingredient can be effectively used for the prevention or treatment of cancer, inflammatory disease or metabolic disease.

The best way to carry out the invention

The present invention is described in detail below.

In one aspect of the present invention, the present invention provides a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof:

[Formula 1]

(In formula 1

Ar is a 6-10 membered aryl or 5-10 membered heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O;

R ¹ and R ² are independently hydrogen, halogen or 5-8 membered heterocycloalkyl C _1-5 alkoxy containing at least one N;

R ³ represents hydrogen, halogen, unsubstituted or substituted straight or branched C _1-8 alkoxy, unsubstituted or substituted straight or branched C _1-8 alkyl, NR ^a1 R ^a2 or OR ^a3 , where R ^a1 , R ^a2 and R ^a3 , independently, are hydrogen, unsubstituted or substituted straight or branched C _1-8 alkyl, unsubstituted or substituted phenyl or 5-8 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O,

wherein substituted alkoxy, substituted alkyl, substituted phenyl and substituted heteroaryl are, independently, substituted with one or more substituents selected from the group consisting of 4-8 membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 4-8 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, NR ^b1 R ^b2 , 3-6 membered cycloalkyl, halogen, hydroxy and sulfonyl, or substituted alkoxy and substituted alkyl can be further substituted to form a 3-6 membered cycloalkyl with each independently substituted carbon atom,

substituted heterocycloalkyl and substituted heteroaryl are substituted with one or more substituents selected from the group consisting of straight or branched C _1-5 alkyl, unsubstituted or substituted by one or more halogens, straight or branched C _1-5 alkylcarbonyl, NR ^b1 R ^b2 , halogen, hydroxy and oxo,

R ^b1 and R ^b2 are independently hydrogen or straight or branched C _1-6 alkyl;

L ¹ represents or , where R ^c represents hydrogen or L ² and forms a 5-8 membered heterocycloalkylene containing N together with the nitrogen atom to which they are attached;

L ² represents a single bond, straight or branched C _1-8 alkylene, C _3-8 cycloalkylene or phenylene, unsubstituted or substituted with one hydroxy and oxo;

Z represents unsubstituted or substituted C _6-10 aryl, C _3-8 cycloalkyl, unsubstituted or fused with a 5-9 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, 4-8-membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 5-9-membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group including N, S and O, or 5-9 membered unsubstituted or substituted heteroaryl C _1-5 alkyl containing one or more heteroatoms selected from the group consisting of N, S and O,

substituted aryl is substituted with halogen, phenyl, carboxy, 4-8 membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, or straight or branched C _1-8 alkoxycarbonyl,

wherein substituted heterocycloalkyl, substituted heteroaryl and substituted heteroarylalkyl are, independently, substituted with one or more substituents selected from the group consisting of straight or branched _C1-5 alkyl, straight or branched _C1-8 alkoxy, phenyl, benzyl, halogen, hydroxy or oxo.)

A compound, its isomer or a pharmaceutically acceptable salt thereof according to claim 1, wherein:

Ar is a 6-10 membered aryl or 5-6 membered heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O;

R ¹ and R ² are independently hydrogen or fluorine;

R ³ represents hydrogen, bromine, unsubstituted or substituted straight or branched C _1-6 alkoxy, unsubstituted or substituted straight or branched C _1-6 alkyl, NR ^a1 R ^a2 or OR ^a3 , where R ^a1 , R ^a2 and R ^a3 , independently, represent hydrogen, unsubstituted or substituted straight or branched C _1-6 alkyl, unsubstituted or substituted phenyl or 5-7 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O,

wherein substituted alkoxy, substituted alkyl, substituted phenyl and substituted heteroaryl are, independently, substituted with one or more substituents selected from the group consisting of 4-7 membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 4-7 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, NR ^b1 R ^b2 , 3-5 membered cycloalkyl, fluorine, bromine, hydroxy and sulfonyl , or substituted alkoxy and substituted alkyl can be further substituted to form a 3-5 membered cycloalkyl with each independently substituted carbon atom,

substituted heterocycloalkyl and substituted heteroaryl are substituted with one or more substituents selected from the group consisting of straight or branched C _1-4 alkyl, unsubstituted or substituted by one or more halogens, straight or branched C _1-4 alkylcarbonyl, NR ^b1 R ^b2 , chlorine, fluorine, bromine, hydroxy and oxo,

R ^b1 and R ^b2 are independently hydrogen or straight or branched C _1-3 alkyl;

L ¹ represents or where R ^c represents hydrogen or L ² and forms piperidinylene together with the nitrogen atom to which they are attached;

L ² represents a single bond, straight or branched C _1-6 alkylene, C _4-6 cycloalkylene or phenylene, unsubstituted or substituted with one hydroxy and oxo;

Z represents unsubstituted or substituted C _6-9 aryl, C _4-7 cycloalkyl, unsubstituted or fused with a 5-9 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, 5-6-membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 6-9-membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group including N, S and O, or 6-9 membered unsubstituted or substituted heteroaryl C _1-4 alkyl containing one or more heteroatoms selected from the group consisting of N, S and O,

substituted aryl substituted with chlorine, phenyl, carboxy, morpholinyl or straight or branched C _1-3 alkoxycarbonyl,

wherein substituted heterocycloalkyl, substituted heteroaryl and substituted heteroarylalkyl are, independently, substituted with one or more substituents selected from the group consisting of straight or branched C _1-4 alkyl, straight or branched C _1-4 alkoxy, benzyl, phenyl, fluorine, chlorine, bromine, hydroxy or oxo.

A compound, its isomer or a pharmaceutically acceptable salt thereof according to claim 1, wherein:

Ar is phenyl, naphthyl, pyridine or triazole;

R ¹ and R ² are independently hydrogen or fluorine;

R ³ represents hydrogen, bromine, unsubstituted or substituted straight or branched C _1-5 alkoxy, unsubstituted or substituted straight or branched C _1-5 alkyl, NR ^a1 R ^a2 or OR ^a3 , where R ^a1 , R ^a2 and R ^a3 , independently, represent hydrogen, unsubstituted or substituted straight or branched C _1-5 alkyl, unsubstituted or substituted phenyl or 5-6 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O,

wherein substituted alkoxy, substituted alkyl, substituted phenyl and substituted heteroaryl are, independently, substituted with one or more substituents selected from the group consisting of 4-7 membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 5-7 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, NR ^b1 R ^b2 , 3-4 membered cycloalkyl, fluorine, bromine, hydroxy and sulfonyl , or substituted alkoxy and substituted alkyl can be further substituted to form cyclopropyl with each independently substituted carbon atom,

substituted heterocycloalkyl and substituted heteroaryl are substituted with one or more substituents selected from the group consisting of straight or branched C _1-3 alkyl, unsubstituted or substituted with one or more fluorine atoms, straight or branched C _1-4 alkylcarbonyl, NR ^b1 R ^b2 , chlorine, fluorine , bromine, hydroxy and oxo,

R ^b1 and R ^b2 are independently hydrogen, methyl or ethyl;

L ¹ represents or where R ^c represents hydrogen or L ² and forms piperidinylene together with the nitrogen atom to which they are attached;

L ² represents a single bond, straight or branched C _1-4 alkylene, cyclohexylene or phenylene, unsubstituted or substituted by one hydroxy and oxo;

Z is an unsubstituted or substituted phenyl, cyclohexyl, naphthyl, C _5-6 cycloalkyl fused with a 5-9 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O, 5-6 -membered unsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, S and O, 6-9 membered unsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, S and O , or 6-9 membered unsubstituted or substituted heteroaryl C _1-3 alkyl containing one or more heteroatoms selected from the group consisting of N, S and O,

substituted phenyl is substituted with chlorine, phenyl, carboxy, morpholinyl or methoxycarbonyl,

wherein substituted heterocycloalkyl, substituted heteroaryl and substituted heteroarylalkyl are, independently, substituted with one or more substituents selected from the group consisting of straight or branched C _1-3 alkyl, methoxy, benzyl, phenyl, fluorine, chlorine, bromo, hydroxy or oxo.

A compound, its isomer or a pharmaceutically acceptable salt thereof according to claim 1, wherein:

Ar is phenyl, naphthyl, pyridine or triazole;

R ¹ and R ² are independently hydrogen or fluorine;

R ³ represents hydrogen, bromine, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , or ;

L ¹ represents , or ;

L ² represents a single bond, , , , , , , or ;

Z represents , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , or .

A compound, an isomer thereof or a pharmaceutically acceptable salt thereof according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:

<1> N-(3-([1,1'-biphenyl]-4-yl)propyl)-4-butoxybenzenesulfonamide;

<2> 4-butoxy-N-(3-(4-isopropylpiperazin-1-yl)propyl)benzenesulfonamide;

<3> 4-butoxy-N-(3-(4-chlorophenyl)propyl)benzenesulfonamide;

<4> 4-butoxy-N-(3-cyclohexylpropyl)benzenesulfonamide;

<5> 4-butoxy-N-(3-(pyridin-3-yl)propyl)benzenesulfonamide;

<6> 4-butoxy-N-(3-morpholinopropyl)benzenesulfonamide;

<7> 4-butoxy-N-(4-morpholinophenethyl)benzenesulfonamide;

<8> 4-(2-(4-butoxyphenylsulfonamido)ethyl)benzoic acid;

<9> methyl 4-(2-(4-butoxyphenylsulfonamido)ethyl)benzoate;

<10> N-(2-(4-benzylpiperidin-1-yl)ethyl)-4-butoxybenzenesulfonamide;

<11> 4-butoxy-N-(3-hydroxy-3-phenylpropyl)benzenesulfonamide;

<12> 4-butoxy-N-(3-oxo-3-phenylpropyl)benzenesulfonamide;

<13> 4-butoxy-N-(3-(2-oxopyrrolidin-1-yl)propyl)benzenesulfonamide;

<14> 4-(3-(dimethylamino)propoxy)-N-phenethylbenzenesulfonamide;

<15> 4-(3-(dimethylamino)propoxy)-N-(3-phenylpropyl)benzenesulfonamide;

<16> methyl 4-(2-(4-(3-(dimethylamino)propoxy)phenylsulfonamido)ethyl)benzoate;

<17> 4-(2-(4-(3-(dimethylamino)propoxy)phenylsulfonamido)ethyl)benzoic acid;

<18> 4-(3-(dimethylamino)propoxy)-N-(3-(2-oxopyrrolidin-1-yl)propyl)benzenesulfonamide;

<19> 4-butoxy-N-(3-(naphthalene-1-yl)propyl)benzenesulfonamide;

<20> N-(3-(1H-indol-3-yl)propyl)-4-butoxybenzenesulfonamide;

<21> N-(3-(1H-indol-3-yl)propyl)-4-(2-(dimethylamino)ethoxy)benzenesulfonamide;

<22> N-(3-(1H-indol-3-yl)propyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide;

<23> N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)-4-butoxybenzenesulfonamide;

<24> N-(2-(1H-indol-3-yl)ethyl)-4-butoxybenzenesulfonamide;

<25> N-(2-(1H-indol-2-yl)ethyl)-4-butoxybenzenesulfonamide;

<26> N-(3-(1H-indol-3-yl)propyl)-4-(isopentyloxy)benzenesulfonamide;

<27> N-(3-(1H-indol-3-yl)propyl)-4-(pentyloxy)benzenesulfonamide;

<28> N-(3-(1H-benzo[d]imidazol-2-yl)propyl)-4-butoxybenzenesulfonamide;

<29> 4-butoxy-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzenesulfonamide;

<30> N-(3-(1H-indol-3-yl)propyl)-4-(3-morpholinopropoxy)benzenesulfonamide;

<31> N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<32> N-(3-(1H-indol-1-yl)propyl)-4-butoxybenzenesulfonamide;

<33> N-(3-(1H-benzo[d]imidazol-1-yl)propyl)-4-butoxybenzenesulfonamide;

<34> N-(3-(1H-benzo[d]imidazol-1-yl)propyl)-4-butoxybenzenesulfonamide;

<35> N-(3-(1H-indol-3-yl)propyl)-4-(3-(diethylamino)propoxy)benzenesulfonamide;

<36> N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-ethylpiperazin-1-yl)propoxy)benzenesulfonamide;

<37> N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide;

<38> N-(2-(1H-indol-2-yl)ethyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide;

<39> N-(3-(1H-indol-1-yl)propyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide;

<40> N-(3-(1H-benzo[d]imidazol-1-yl)propyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide;

<41> N-(3-(1H-indol-1-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<42> N-(3-(1H-benzo[d]imidazol-1-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<43> N-(3-(1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzenesulfonamide;

<44> N-(3-(1H-indol-3-yl)propyl)-4-(3-(2-oxopyrrolidin-1-yl)propoxy)benzenesulfonamide;

<45> N-(3-(1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<46> 4-(3-(dimethylamino)propoxy)-N-(3-(1-methyl-1H-indol-3-yl)propyl)benzenesulfonamide;

<47> N-(3-(1H-indol-3-yl)propyl)-4-bromobenzenesulfonamide;

<48> N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-isopropylpiperazin-1-yl)propoxy)benzenesulfonamide;

<49> N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<50> N-(2-(1H-indol-3-yl)ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<51> N-(2-(1H-indol-3-yl)ethyl)-4-(3-(4-isopropylpiperazin-1-yl)propoxy)benzenesulfonamide;

<52> N-(3-(1H-indol-3-yl)propyl)-4-(2-(4-methylpiperazin-1-yl)ethoxy)benzenesulfonamide;

<53> N-(3-(1H-indol-3-yl)propyl)-4-(2-(4-isopropylpiperazin-1-yl)ethoxy)benzenesulfonamide;

<54> N-(2-(2-methyl-1H-indol-3-yl)ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<55> N-(3-(1H-indol-3-yl)propyl)-4-(2-(1-methylpiperidin-4-yl)ethoxy)benzenesulfonamide;

<56> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<57> 3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)sulfonyl)piperidin-4-yl)-1H-indole;

<58> N-(3-(2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<59> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzenesulfonamide;

<60> N-(3-(1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzenesulfonamide;

<61> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<62> N-(3-(1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<63> 4-(3-(4-ethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl)benzenesulfonamide;

<64> 5-methoxy-3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)sulfonyl)piperidin-4-yl)-1H-indole;

<65> 5-methyl-3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)sulfonyl)piperidin-4-yl)-1H-indole;

<66> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<67> N-(3-(5-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<68> N-(3-(5-methoxy-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<69> N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-hydroxypiperidin-1-yl)propoxy)benzenesulfonamide;

<70> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<71> 5-fluoro-3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)sulfonyl)piperidin-4-yl)-1H-indole;

<72> 4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl)benzenesulfonamide;

<73> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-isobutyrylpiperazin-1-yl)propoxy)benzenesulfonamide;

<74> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)propoxy)benzenesulfonamide ;

<75> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-hydroxypiperidin-1-yl)propoxy)benzenesulfonamide;

<76> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)propoxy)benzenesulfonamide ;

<77> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-(methylamino)azetidin-1-yl)propoxy)benzenesulfonamide;

<78> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-chloropiperidin-1-yl)propoxy)benzenesulfonamide;

<79> N-(3-(5-chloro-1H-indol-3-yl)propyl)-6-(3-(piperazin-1-yl)propoxy)pyridin-3-sulfonamide;

<80> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-fluoropiperidin-1-yl)propoxy)benzenesulfonamide;

<81> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-(trifluoromethyl)piperidin-1-yl)propoxy)benzenesulfonamide;

<82> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,4-difluoropiperidin-1-yl)propoxy)benzenesulfonamide;

<83> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-1,4-diazepan-1-yl)propoxy)benzenesulfonamide;

<84> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzenesulfonamide;

<85> N-(3-(1H-indol-3-yl)cyclohexyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<86> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)naphthalene-1-sulfonamide;

<87> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzenesulfonamide;

<88> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-4-yl)propyl)amino)benzenesulfonamide;

<89> N-(3-(1H-indol-3-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<90> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-1-yl)butyl)benzenesulfonamide;

<91> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperazin-1-yl)butyl)benzenesulfonamide;

<92> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzenesulfonamide;

<93> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-4-yl)propoxy)benzenesulfonamide;

<94> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperidin-4-yl)propoxy)benzenesulfonamide;

<95> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperidin-1-yl)propoxy)benzenesulfonamide;

<96> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<97> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperidin-4-yl)propoxy)benzenesulfonamide;

<98> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methylpiperazin-1-yl)propyl)amino)benzenesulfonamide;

<99> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-4-yl)butyl)benzenesulfonamide;

<100> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyrrolidin-1-yl)propoxy)benzenesulfonamide;

<101> 4-(3-(azepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<102> 4-(3-(1,4-diazepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<103> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<104> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<105> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-hydroxypiperidin-1-yl)propoxy)benzenesulfonamide;

<106> 4-(3-(1,4-diazepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluorobenzenesulfonamide;

<107> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<108> (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<109> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<110> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)benzenesulfonamide;

<111> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3,4-dimethylpiperazin-1-yl)propoxy)benzenesulfonamide;

<112> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(4-methylpiperazin-1-yl)butyl)benzenesulfonamide;

<113> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperazin-1-yl)propyl)amino)benzenesulfonamide;

<114> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-1-yl)propyl)amino)benzenesulfonamide;

<115> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(1-methylpiperidin-4-yl)butyl)benzenesulfonamide;

<116> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-((4-methylpiperazin-1-yl)methyl)cyclopropyl)methoxy)benzenesulfonamide;

<117> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-(piperazin-1-ylmethyl)cyclopropyl)methoxy)benzenesulfonamide;

<118> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)phenoxy)benzenesulfonamide;

<119> 4-(3-bromophenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<120> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)phenoxy)benzenesulfonamide;

<121> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)phenoxy)benzenesulfonamide;

<122> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-1,4-diazepan-1-yl)phenoxy)benzenesulfonamide;

<123> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methylpiperazin-1-yl)phenyl)amino)benzenesulfonamide;

<124> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperazin-1-yl)phenyl)amino)benzenesulfonamide;

<125> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)pyrimidin-2-yl)amino)benzenesulfonamide;

<126> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-morpholinophenyl)amino)benzenesulfonamide;

<127> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(piperazin-1-yl)pyrimidin-2-yl)amino)benzenesulfonamide;

<128> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-morpholinophenoxy)benzenesulfonamide;

<129> 4-(3-(1,4-diazepan-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<130> 4-(3,5-bis(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<131> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide;

<132> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-(piperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide;

<133> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide;

<134> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(piperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide;

<135> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyrrolidin-1-yl)phenoxy)benzenesulfonamide;

<136> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-hydroxypiperidin-1-yl)phenoxy)benzenesulfonamide;

<137> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-fluoro-5-(4-methylpiperazin-1-yl)phenoxy)benzenesulfonamide;

<138> 4-(3-bromo-5-(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<139> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-hydroxypiperidin-1-yl)phenyl)amino)benzenesulfonamide;

<140> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-chloro-4-(4-methylpiperazin-1-yl)pyridin-2-yl)amino )benzenesulfonamide;

<141> 4-((4,6-bis(4-methylpiperazin-1-yl)pyridin-2-yl)amino)-N-(3-(5-chloro-1H-indol-3-yl)propyl) benzenesulfonamide;

<142> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)phenyl)amino)benzenesulfonamide;

<143> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzamide;

<144> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzamide;

<145> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(methylsulfonyl)propoxy)benzenesulfonamide;

<146> N-(3-(5-chloro-1H-indol-3-yl)propyl)-2-((3-(piperazin-1-yl)propyl)amino)triazole-5-sulfonamide;

<147> N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<148> 4-(4-(1H-imidazol-1-yl)butyl)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<149> N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<150> N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<151> N-(4-(5-chloro-1H-indol-3-yl)butan-2-yl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<152> N-(4-(5-chloro-1H-indol-3-yl)butan-2-yl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<153> N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<154> N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<155> N-(3-(5-phenyl-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<156> 4-(3-(4-methylpiperazin-1-yl)propoxy)-N-(3-(5-phenyl-1H-indol-3-yl)propyl)benzenesulfonamide;

<157> N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<158> N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<159> N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<160> 4-(3-(1H-1,2,4-triazol-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide;

<161> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(2-methyl-1H-imidazol-1-yl)propoxy)benzenesulfonamide;

<162> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-3-oxopiperazin-1-yl)propoxy)benzenesulfonamide;

<163> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-oxopiperazin-1-yl)propoxy)benzenesulfonamide;

<164> N-(3-(5,7-dichloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<165> N-(3-(5,7-dichloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<166> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,5-dichloro-1H-imidazol-1-yl)propoxy)benzenesulfonamide;

<167> N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<168> N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<169> N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<170> N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<171> (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<172> (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<173> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<174> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<175> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,5-dimethyl-1H-imidazol-1-yl)propoxy)benzenesulfonamide;

<176> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(2,4,5-trimethyl-1H-imidazol-1-yl)propoxy)benzenesulfonamide;

<177> N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<178> N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<179> N-(3-(5-chloro-1H-indol-3-yl)cyclohexyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<180> N-(3-(5-chloro-1H-indol-3-yl)cyclohexyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<181> N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide ;

<182> N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<183> N-(3-(5,6-dichloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<184> N-(3-(5,6-dichloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<185> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyridin-4-yloxy)propyl)benzenesulfonamide;

<186> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propyl)benzenesulfonamide;

<187> N-((6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide;

<188> N-((6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide;

<189> 4-(3-(4-methylpiperazin-1-yl)propoxy)-N-((2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)benzenesulfonamide;

<190> 4-(3-(piperazin-1-yl)propoxy)-N-((2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)benzenesulfonamide.

The compound represented by Formula 1 of the present invention can be used as a pharmaceutically acceptable salt, wherein the salt is preferably an acid addition salt formed by pharmaceutically acceptable free acids. The acid addition salt of the present invention can be obtained from inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, nitrous acid and phosphorous acid; non-toxic organic acids such as aliphatic mono/dicarboxylates, phenyl-substituted alkanoates, hydroxyalkanoates, alkanedioates, aromatic acids and aliphatic/aromatic sulfonic acids; or organic acids such as acetic acid, benzoic acid, citric acid, lactic acid, maleic acid, gluconic acid, methanesulfonic acid, 4-toluenesulfonic acid, tartaric acid and fumaric acid. Examples of pharmaceutically non-toxic salts are sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogen phosphate, dihydrogen phosphate, metaphosphate, pyrophosphate, chloride, bromide, iodide, fluoride, acetate, propionate, decanoate, caprylate, acrylate, formate, isobutylate, caprate , heptanoate, propiolate, oxalate, malonate, succinate, suberate, kabacat, fumarate, maliat, butine-1,4-dioate, hexane-1,6-dioate, benzoate, chlorobenzoate, methyl benzoate, dinitrobenzoate, hydroxybenzoate, methoxybenzoate, phthalate, terephthalate , benzenesulfonate, toluenesulfonate, chlorobenzenesulfonate, xylenesulfonate, phenylacetate, phenylpropionate, phenylbutylate, citrate, lactate, hydroxybutylate, glycolate, malate, tartrate, methanesulfonate, propanesulfonate, naphthalene-1-sulfonate, naphthalene-2-sulfonate and mandelate.

The acid addition salt of the present invention can be prepared by a conventional method known to those skilled in the art. For example, the derivative represented by Formula 1 is dissolved in an organic solvent such as methanol, ethanol, acetone, dichloromethane and acetonitrile, to which an organic acid or an inorganic acid is added to cause precipitation. The precipitate is then filtered and dried to obtain salt. Or the solvent and excess acid are distilled under reduced pressure and dried to obtain a salt. Or the precipitate is crystallized in an organic solvent to obtain the same.

A pharmaceutically acceptable metal salt can be prepared using a base. An alkali metal or alkaline earth metal salt is prepared by the following methods: by dissolving the compound in an excess solution of alkali metal hydroxide or alkaline earth metal hydroxide; filtering the insoluble salt compound; by evaporating the remaining solution and drying it. At this time, the metal salt is preferably obtained in a pharmaceutically suitable form as a sodium, potassium or calcium salt. And the corresponding silver salt is obtained by reacting an alkali metal or alkaline earth metal salt with a corresponding silver salt (for example, silver nitrate).

Moreover, the present invention includes not only the compound represented by Formula 1 and its pharmaceutically acceptable salt, but also the solvates, isomers, hydrates, etc. that can be prepared therefrom.

The term "isomer" refers to a compound of the present invention or a salt thereof having the same chemical formula or molecular formula but differing structurally or sterically. Such isomer includes structural isomers such as tautomers, R- or S-isomers having an asymmetric carbon center, stereoisomers such as geometric isomers (trans-, cis-) and optical isomers. All of these isomers and mixtures thereof are also included within the scope of the present invention.

The compound represented by Formula 1 of the present invention can be produced in accordance with the production method shown in the following example, but this is only an example and is not limited to it, and each production step can be carried out using a method well known to those skilled in the art.

In another aspect of the present invention, the present invention relates to a method for producing a compound represented by Formula 1, comprising the step of producing a compound represented by Formula 1 by reacting a compound represented by Formula 2 with a compound represented by Formula 3, as shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

In the reaction scheme 1, Ar, R ¹ , R ² , R ³ , L ¹ , L ² and Z have the meanings defined in formula 1 above,

J ¹ represents chlorosulfone or carboxy; And

J ² represents an amine or piperidine.

The preparation method shown in Reaction Scheme 1 is described in detail below.

In the method for producing the compound represented by Formula 1 of the present invention, reaction scheme step 1 is a step of producing the compound represented by Formula 1 by reacting the compound represented by Formula 2 with the compound represented by Formula 3. Specifically, it is a step in which the compound , represented by Formula 1, is formed by reacting the chlorosulfone or carboxy group of the compound represented by Formula 2 with the amine of the compound represented by Formula 3.

However, this step is not particularly limited as long as it is a method for producing the compound represented by Formula 1 and falls within the scope of the present invention. The compound represented by Formula 2 can be understood as a compound having a group that readily accepts electrons, such as a sulfone, and a leaving group that readily reacts, such as chlorine, or a compound containing a carboxyl group that can react with an amine with amide formation, and the compound represented by Formula 3 can be understood as, but is not always limited to, an amine capable of undergoing nucleophilic substitution or amide formation reactions. A compound having a group that readily accepts electrons and a leaving group and an amine having sufficient nucleophilicity to react with it undergoes nucleophilic substitution, or a carboxy group and an amine undergo an amide formation reaction, resulting in the final compound.

In more detail, this can be understood in relation to the method for preparing an example of the compound of the present invention, but each reaction condition (reaction condition that can be considered by a person skilled in the art of organic synthesis, such as reaction temperature, time, atmospheric conditions, pressure conditions, etc.) can be changed. .d.). It will be understood that the invention is not limited to this, and the compounds and derivatives thereof used in each step include modified derivatives that can be modified by simple modification, alteration or removal of a substituent, in addition to the described compounds which are included in the present invention.

Preferred embodiments of the production method include the production methods described in Examples 1 to 190 below, but the present invention is not limited to them.

In another aspect of the present invention, the present invention relates to a pharmaceutical composition containing, as an active ingredient, a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof, for the prevention or treatment of cancer, an inflammatory disease, or a metabolic disease.

The compound represented by Formula 1 of the present invention, an isomer thereof, or a pharmaceutically acceptable salt thereof can inhibit Pin1 (peptidyl-prolyl cis-trans isomerase interacting with 1).

Pin1, a prolyl isomerase, is an enzyme that catalyzes the cis/trans isomerization of the amide residue of proline by binding to the phosphorylated Ser/Thr-Pro site. Based on research to date, Pin1 is known to be involved in the initiation and progression of inflammatory disease, metabolic disease, and malignancy.

In particular, Pin1 has been reported to activate 56 oncogenes involved in tumorigenesis and inhibit the activity of 26 tumor suppressor genes, thereby inducing cancer metastasis and cancer angiogenesis in the overall mechanism of cancer development.

In addition, it has been reported that when Pin1 is inhibited or Pin1 gene expression is suppressed, the production of prostaglandin E2 and nitric oxide stimulated by lipopolysaccharide (LPS) and nicotine is attenuated, and the expression of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) is also reported. are weakened, which leads to an anti-inflammatory effect.

It is well known that when Pin1 is attached to CRTC2, the production of the CBP-CRTC2-CREB complex, which promotes gluconeogenesis, is inhibited, so that CRTC2 may be regulated according to the expression level of Pin1 and thus may participate in glucose regulation. metabolism.

Thus, drugs that affect the expression or activity of Pin1 can be used as therapeutic agents for a malignancy, an inflammatory disease, or a metabolic disease such as diabetes.

Thus, the compound represented by Formula 1 of the present invention, its isomer or a pharmaceutically acceptable salt thereof can be effectively used as a pharmaceutical composition for the prevention or treatment of malignancy, inflammatory disease or metabolic disease, or a functional health product containing the same in as an active ingredient for the prevention or amelioration of malignancy, inflammatory disease or metabolic disease.

The malignancy may be at least one selected from the group consisting of pseudomyxoma, intrahepatic cholangiocarcinoma, hepatoblastoma, liver cancer, thyroid cancer, colon cancer, testicular cancer, myelodysplastic syndrome, glioblastoma, oral cancer, lip cancer, mycosis fungoides , acute myelogenous leukemia, acute lymphocytic leukemia, basal cell carcinoma, epithelial ovarian carcinoma, ovarian germ cell carcinoma, male breast cancer, brain cancer, pituitary adenoma, multiple myeloma, gallbladder cancer, biliary tract cancer, colorectal cancer, chronic myelogenous leukemia , chronic lymphocytic leukemia, retinoblastoma, choroidal melanoma, Vater ampullary cancer, bladder cancer, peritoneal cancer, parathyroid cancer, adrenal cancer, nasal cavity cancer, non-small cell lung cancer, tongue cancer, astrocytoma, small cell lung cancer, pediatric brain cancer, pediatric lymphoma , childhood leukemia, small bowel cancer, meningioma, esophageal cancer, glioma, kidney cancer, kidney cancer, heart cancer, duodenal cancer, malignant soft tissue cancer, malignant bone cancer, malignant lymphoma, malignant mesothelioma, malignant melanoma, eye cancer, cancer vulva, urethral cancer, cancer of unknown primary site, gastric lymphoma, stomach cancer, gastric cancer, interstitial cancer of the gastrointestinal tract, Wilms cancer, breast cancer, sarcoma, penile cancer, pharyngeal cancer, villous disease of pregnancy, cervical cancer, endometrial cancer, uterine sarcoma, prostate cancer, metastatic bone cancer, metastatic brain cancer, mediastinal cancer, rectal cancer, rectal carcinoid tumor, vaginal cancer, spinal cord cancer, vestibular schwannoma, pancreatic cancer, salivary gland cancer, sarcoma Kaposi's disease, Paget's disease, tonsil cancer, squamous cell carcinoma, lung adenocarcinoma, lung cancer, squamous cell lung cancer, skin cancer, anal cancer, rhabdomyosarcoma, laryngeal cancer, pleural cancer, blood cancer and thymus cancer.

The inflammatory disease may be at least one selected from the group consisting of arthritis, encephalomyelitis, meningitis, peritonitis, osteomyelitis, encephalitis, ankylosing spondylitis, vasculitis, uveitis, ileitis, atherosclerosis, myositis, leukocyte disease, inflammatory bowel disease, ulcerative colitis, retinal detachment, retinitis pigmentosa, macular degeneration, pancreatitis, atopic dermatitis, gout, vasculitis, non-alcoholic steatohepatitis, primary sclerosing cholangitis, nephritis, intraperitoneal disease, sepsis, systemic inflammatory response syndrome, myocardial infarction, allergic diseases, asthma, atopic dermatitis, granulomatosis Wegener's, pulmonary sarcoidosis, Behçet's disease, chronic obstructive pulmonary disease and periodontitis.

The metabolic disease may be at least one selected from the group consisting of obesity, diabetes, hypertension, hyperlipidemia, hypercholesterolemia, atherosclerosis, fatty liver, gout, stroke and heart disease.

In another aspect of the present invention, the present invention relates to a functional health product containing as an active ingredient a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof, for the prevention or amelioration of cancer, an inflammatory disease, or a metabolic disease.

The term "prevention" as used in the present invention refers to any action that suppresses or delays the onset of a neurological disorder by administering to a subject a pharmaceutical composition of the present invention.

The term "treatment" as used in the present invention refers to any action to improve or alleviate the symptoms of a neurological disorder by administering to a subject a pharmaceutical composition of the present invention.

When the composition of the present invention is used as a medicinal product, a pharmaceutical composition containing as an active ingredient the compound represented by Formula 1, an isomer thereof or a pharmaceutically acceptable salt thereof can be formulated and administered in various oral or parenteral forms as appropriate according to clinical administration, but it is not always limited to this.

Examples of oral formulations are tablets, pills, hard/soft capsules, solutions, suspensions, emulsions, syrups, granules, elixirs, lozenges, etc. These formulations may include diluents (e.g., lactose, dextrose, sucrose, mannitol, sorbitol, cellulose and/or glycine) and lubricants (for example, silicon dioxide, talc, stearate and its magnesium or calcium salts and/or polyethylene glycol). Tablets may include binding agents such as magnesium aluminosilicate, starch paste, gelatin, methylcellulose, sodium carboxymethylcellulose and/or polyvinylpyrrolidone, and optionally disintegrating agents such as starch, agarose, alginic acid or its sodium salt or azeotropic mixtures and/or absorbents, additionally, colors, flavors and sweeteners may be included.

When a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof is used as a pharmaceutical composition for the prevention or treatment of a malignancy, an inflammatory disease or a metabolic disease, it can be administered as a single therapeutic agent or it can be used in combination with other therapeutic agents used. .

The pharmaceutical composition containing as an active ingredient the compound represented by Formula 1 or a pharmaceutically acceptable salt thereof can be administered parenterally, and parenteral administration includes subcutaneous injection, intravenous injection, intramuscular injection or intrathoracic injection.

To prepare the compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof in a parenteral dosage form, the compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof is mixed with a stabilizer or buffering agent in water to obtain a solution or suspension that then prepared in the form of ampoules or vials. The composition herein may be sterilized and further contain preservatives, stabilizers, wettable powders or emulsifiers, salts and/or buffers to regulate osmotic pressure and other therapeutically useful materials, and the composition may be formulated according to conventional methods such as dispersion and gelation .

The dosage of a pharmaceutical composition containing the compound represented by Formula 1 as an active ingredient for the human body can be determined according to the method of preparation, age, body weight, gender, route of administration, health status and severity of the disease. The preferred dose of the composition of the present invention is 0.001~1000 μg/ml per day, which can be administered orally or parenterally several times a day or preferably 1~3 times a day as determined by a physician or pharmacist.

The pharmaceutical composition of the present invention can be used as a separate preparation. The pharmaceutical composition of the present invention can also be formulated and used as a combination preparation further comprising one or more other therapeutic agents.

In another aspect of the present invention, the present invention relates to a method of treating a cancer, inflammatory disease or metabolic disease, comprising the step of administering a pharmaceutical composition to a subject in need thereof. Pharmaceutical composition refers to a pharmaceutical composition for the prevention or treatment of malignancy, inflammatory disease or metabolic disease, containing as an active ingredient a compound represented by Formula 1, an isomer thereof or a pharmaceutically acceptable salt thereof.

In another aspect of the present invention, the present invention relates to the use of a pharmaceutical composition or a functional health product composition containing, as an active ingredient, a compound represented by Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof, for the prevention or treatment of a malignancy, an inflammatory disease, or a metabolic disease.

Method for carrying out the invention

Next, the present invention is described in detail using the following examples and experimental examples.

However, the following examples and experimental examples are intended only to illustrate the present invention, and the content of the present invention is not limited to them.

<Example 1> Preparation of N-(3-([1,1' -biphenyl]-4-yl)propyl)-4-butoxybenzenesulfonamide

Step 1: Preparation of (E)-4-(2-isocyanovinyl)-1,1' - biphenyl

Sodium hydride (60% wt, 0.263 g, 6.59 mmol) was dissolved in anhydrous tetrahydrofuran (13 ml), diethyl (cyanomethyl)phosphonate (0.977 ml, 6.04 mmol) was added dropwise at 0°C. [1,1'-Biphenyl]-4-carbaldehyde (1 g, 5.49 mmol) was added dropwise to the reaction mixture, then stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The result was (E)-4-(2-isocyanovinyl)-1,1'-biphenyl as a white solid without further purification.

Step 2: Preparation of 3-([1,1' -biphenyl]-4-yl)propanenitrile

The compound (1.126 g, 5.49 mmol) obtained in step 1 above was dissolved in ethyl acetate:methanol (1:1) (24 ml), Pd/C (10% wt) was added dropwise at 0°C, then stirred at room temperature for 12 hours under a hydrogen atmosphere. After completion of the reaction, the reaction mixture was filtered through celite and the solvent was removed under reduced pressure. As a result, 3-([1,1'-biphenyl]-4-yl)propanenitrile was obtained in the form of a white solid without further purification.

Step 3: Preparation of 3-([1,1' -biphenyl]-4-yl)propan-1-amine

The compound 3-([1,1'-biphenyl]-4-yl)propanenitrile (1.137 g, 5.49 mmol) synthesized in step 2 above was dissolved in anhydrous tetrahydrofuran (10 ml), at a temperature of 0°C added drops of 1 M lithium aluminum hydride (10.97 mL, 10.97 mmol), then stirred at room temperature for 2 hours. The reaction was completed by adding water dropwise and the reaction mixture was filtered through a filter and the solvent was removed under reduced pressure. As a result, 3-([1,1'-biphenyl]-4-yl)propan-1-amine was obtained in the form of a yellow sticky compound without further purification.

Step 4: Preparation of N-(3-([1,1' -biphenyl]-4-yl)propyl)-4-butoxybenzenesulfonamide

4-Butoxy benzenesulfonyl chloride (40 μl, 0.200 mmol) was dissolved in dichloromethane (1 ml), 3-([1,1'-biphenyl]-4-yl)propan-1-amine (127 mg, 0.601 mmol), synthesized, was added in step 3 above, then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (14.4 mg, 16%, white solid).

The compounds of examples 2-7 were prepared similarly to the method described in step 4 of example 1.

<Example 8> Preparation of 4-(2-(4-butoxyphenylsulfonamido)ethyl)benzoic acid

Step 1: Preparation of methyl 4-(2-((4-butoxyphenyl)sulfonamido)ethyl)benzoate

The target compound (6.7 mg, 28%, white solid) was prepared analogously to the method described in step 4 of example 1.

Step 2: Preparation of 4-(2-(4-butoxyphenylsulfonamido)ethyl)-benzoic acid

The compound methyl 4-(2-((4-butoxyphenyl)sulfonamido)ethyl)benzoate (23 mg, 0.059 mmol) obtained in step 1 above was dissolved in methanol (0.5 ml), 4 M aqueous hydroxide solution was added dropwise potassium (0.147 ml, 0.588 mmol), then stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was neutralized using 1 M aqueous HCl solution. The reaction mixture was extracted with dichloromethane, and the organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (3.4 g, 15%, white solid).

The compound of Example 9 was prepared in the same manner as described in Step 1 of Example 8.

<Example 10> Preparation of N-(2-(4-benzylpiperidin-1-yl)ethyl)-4-butoxybenzenesulfonamide

Step 1: Preparation of tert-butyl (2-(4-benzylpiperidin-1-yl)ethyl)carbamate

4-Benzylpiperidine (8 g, 45.6 mmol) and potassium carbonate (K ₂ CO ₃ ) (9.46 g, 68.5 mmol) were dissolved in DMF (228 ml), then stirred at room temperature for 5 minutes. Tert-butyl(2-bromoethyl)carbamate (12.27 g, 54.8 mmol) was added dropwise to the reaction mixture, then stirred at 60°C for 12 hours. Tert-butyl(2-bromoethyl)carbamate (12.27 g, 54.8 mmol) was again added dropwise to the reaction product, then stirred at 60°C for 12 hours. After completion of the reaction, 1 M aqueous HCl solution was added dropwise, then extracted with dichloromethane. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give tert-butyl (2-(4-benzylpiperidin-1-yl)ethyl)carbamate (12.9 g, 89%, white solid).

Step 2: Preparation of 2⋅HCl salt of 2-(4-benzylpiperidin-1-yl)ethanamine

Tert-butyl (2-(4-benzylpiperidin-1-yl)ethyl)carbamate (12.9 g, 40.5 mmol) obtained in step 1 above was directly treated with 4 M HCl in dioxane (10.13 mL, 40.5 mmol), then stirred at room temperature for 2 hours. After completion of the reaction, excess HCl was removed under reduced pressure. The result was 2.times.HCl 2-(4-benzylpiperidin-1-yl)ethanamine salt (8.9 g, 75%, white solid).

Step 3: Preparation of N-(2-(4-benzylpiperidin-1-yl)ethyl)-4-butoxybenzenesulfonamide

The target compound (7.6 mg, 14%, clear oil) was prepared similarly to the method described in step 4 of example 1, using the compound obtained in step 2 above.

The compound of Example 11 was prepared analogously to the method described in step 4 of Example 1.

<Example 12> Preparation of 4-butoxy-N-(3-oxo-3-phenylpropyl)benzenesulfonamide

Step 1: Preparation of (4-butoxy-N-(3-hydroxy-3-phenylpropyl)benzenesulfonamide

The target compound was prepared analogously to the method described in step 4 of example 1.

Step 2: Preparation of 4-butoxy-N-(3-oxo-3-phenylpropyl)benzenesulfonamide

The compound (30 mg, 0.121 mmol) obtained in step 1 above was dissolved in dichloromethane (0.5 ml), manganese (IV) oxide (31.1 mg, 0.358 mmol) was added dropwise, then stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was filtered through celite and the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (9.2 mg, 71%, white solid).

The compound of Example 13 was prepared analogously to the method described in step 4 of Example 1.

<Example 14> Preparation of 4-(3-(dimethylamino)propoxy)-N-phenethylbenzenesulfonamide

Step 1: Preparation of N,N-dimethyl-3-phenoxypropan-1-amine

Phenol (600 mg, 6.38 mmol), 3-(dimethylamino)propan-1-ol (0.88 ml, 7.44 mmol) and triphenylphosphine (2.508 g, 9.56 mmol) were dissolved in tetrahydrofuran (12 ml) at 0°C, a solution of diethyl azodicarboxylate (DEAD) (4.34 mL, 9.56 mmol) was added dropwise, then stirred at room temperature for 12 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was removed under reduced pressure. The reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give N,N-dimethyl-3-phenoxypropan-1-amine (922 mg, 81%, yellow oil).

Step 2: Preparation of 4-(3-(dimethylamino)propoxy)benzene-1-sulfonyl chloride

N,N-dimethyl-3-phenoxypropan-1-amine (922 mg, 5.14 mmol) obtained in step 1 above was dissolved in dichloromethane (6 ml), chlorosulfonic acid (1.37 ml, 20. 57 mmol), then stirred at room temperature for 3 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with dichloromethane, and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. This gave 4-(3-(dimethylamino)propoxy)benzene-1-sulfonyl chloride (451 mg, 32%, yellow solid) without further purification.

Step 3: Preparation of 4-(3-(dimethylamino)propoxy)-N-phenethylbenzenesulfonamide

4-(3-(Dimethylamino)propoxy)benzene-1-sulfonyl chloride (100 mg, 0.318 mmol) obtained in step 2 above was dissolved in dichloromethane (2 ml), 2-phenylethanamine (116 mg, 0.955 mmol) was added dropwise. and potassium carbonate (K ₂ CO ₃ ) (48.4 mg, 0.35 mmol), then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (88 mg, 75%, clear oil).

The compounds of Examples 15 and 16 were prepared similarly to the method described in step 3 of Example 14.

<Example 17> Preparation of 4-(2-(4-(3-(dimethylamino)propoxy)phenylsulfonamido)ethyl)benzoic acid

Step 1: Preparation of methyl 4-(2-(4-(3-(dimethylamino)propoxy)phenylsulfonamido)ethyl)benzoate

The target compound was prepared analogously to the method described in step 3 of example 14.

Step 2: Preparation of 4-(2-(4-(3-(dimethylamino)propoxyphenylsulfonamido)ethyl)benzoic acid

The compound (58 mg, 0.138 mmol) obtained in step 1 above was dissolved in methanol (1 ml), 4 M aqueous potassium hydroxide solution (0.69 ml, 2.76 mmol) was added dropwise, then stirred at room temperature in within 1 hour. After completion of the reaction, the reaction mixture was neutralized with 1 M aqueous HCl, extracted with dichloromethane, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by TLC to give the title compound (1.7 mg, 3%, white solid).

The compound of Example 18 was prepared analogously to the method described in step 3 of Example 14.

<Example 19> Preparation of 4-butoxy-N-(3-(naphthalene-1-yl)propyl)benzenesulfonamide

Step 1: Preparation of tert-butyl(3-(naphthalene-1-yl)propyl)carbamate

Tert-butylallylcarbamate (1 g, 6.36 mmol) was dissolved in tetrahydrofuran (6 ml), 9-BBN (10 mmol) dissolved in 0.5 M tetrahydrofuran was added dropwise, then stirred at room temperature for 2.5 hours . 1-Iodonaphthalene (0.925 ml, 6.36 mmol), PdCl ₂ (dppf)-CH ₂ Cl ₂ (308 mg, 0.377 mmol) and 1 M aqueous sodium hydroxide solution (10 ml) were added dropwise to the reaction mixture, then stirred at room temperature for 3 hours. PdCl ₂ (dppf)-CH ₂ Cl ₂ (55 mg, 0.07 mmol) was added dropwise, then stirred at room temperature for 14 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added dropwise, and the reaction mixture was extracted with ethyl acetate, dried over magnesium sulfate, and the solvent was removed under reduced pressure. Then, to a mixture of tetrahydrofuran (20 ml), 15% aqueous sodium hydroxide (5 ml) and 30% hydrogen peroxide (10 ml) at a temperature of 0°C, the compound (1.6 g) obtained by isolating and purifying the reaction mixture was added dropwise using HPLC, then stirred at the same temperature for 2 hours. After completion of the reaction, ethyl acetate was added dropwise, and the reaction mixture was washed with a supersaturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give tert-butyl (3-(naphthalene-1-yl)propyl)carbamate (1.4 g, 77%).

Step 2: Preparation of 3-(naphthalene-1-yl)propan-1-amine

Tert-butyl(3-(naphthalene-1-yl)propyl)carbamate (1.4 g, 4.9 mmol) obtained in step 1 above was dissolved in dichloromethane (20 ml), trifluoroacetic acid (10 ml) was added dropwise , 130 mmol), then stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was neutralized by adding dropwise 10% aqueous sodium hydroxide solution. The reaction mixture was extracted with dichloromethane, and the organic layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 3-(naphthalene-1-yl)propan-1-amine (925 mg, 100% ).

Step 3: Preparation of 4-butoxy-N-(3-(naphthalene-1-yl)propyl)benzenesulfonamide

The target compound (66 mg, 82%, clear solid) was prepared similarly to the method described in step 4 of example 1 using the compound obtained in step 2 above.

The compound of Example 20 was prepared analogously to the method described in step 4 of Example 1.

<Example 21> Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(2-(dimethylamino)ethoxy)benzenesulfonamide

Step 1: Preparation of N,N-dimethyl-2-phenoxyethane-1-amine

Phenol (500 mg, 5.31 mmol), 2-(dimethylamino)ethan-1-ol (521 mg, 5.84 mmol) and triphenylphosphine (2.089 g, 797 mmol) were dissolved in tetrahydrofuran (20 ml) at 0°C ), a solution of diethyl azodicarboxylate (DEAD) (3.61 mL, 7.97 mmol) was added dropwise, then stirred at room temperature for 12 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was removed under reduced pressure. The reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give N,N-dimethyl-2-phenoxyethane-1-amine (870 mg, 99%, yellow solid).

Step 2: Preparation of 4-(2-(dimethylamino)ethoxy)benzenesulfonyl chloride

N,N-dimethyl-3-phenoxyethane-1-amine (533 mg, 3.23 mmol) obtained in step 1 above was dissolved in dichloromethane (3 ml), chlorosulfonic acid (0.858 ml) was added dropwise at 0°C , 12.90 mmol), then stirred at room temperature for 3 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with dichloromethane and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The resulting 4-(2-(dimethylamino)ethoxy)benzenesulfonyl chloride (622 mg, 73%, yellow oil) was obtained without further purification.

Step 3: Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(2-(dimethylamino)ethoxy)benzenesulfonamide

4-(2-(Dimethylamino)ethoxy)benzenesulfonyl chloride (45 mg, 0.171 mmol) obtained in step 2 above was dissolved in dichloromethane, 3-(1H-indol-3-yl)propan-1-amine ( 131 mg, 0.751 mmol), then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (11 mg, 17%, yellow solid).

The compound of example 22 was prepared similarly to the method described in example 14.

The compounds of examples 23-25 were prepared similarly to the method described in step 4 of example 1.

<Example 26> Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(isopentyloxy)benzenesulfonamide

4-(Isopentyloxy)benzenesulfonyl chloride (20 mg, 0.076 mmol) was dissolved in dichloromethane (1.5 ml), 3-(1H-indol-3-yl)propan-1-amine (30 mg, 0.172 mmol) was added dropwise. then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (26 mg, 85%, yellow solid).

<Example 27> Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(pentyloxy)benzenesulfonamide

4-(Pentyloxy)benzenesulfonyl chloride (20 mg, 0.076 mmol) was dissolved in dichloromethane, 3-(1H-indol-3-yl)propan-1-amine (30 mg, 0.172 mmol) was added dropwise, then stirred at room temperature within 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (25 mg, 81%, white solid).

The compound of Example 28 was prepared analogously to the method described in step 4 of Example 1.

<Example 29> Preparation of 4-butoxy-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzenesulfonamide

4-Butoxy benzenesulfonyl chloride (50 mg, 0.201 mmol) was dissolved in dichloromethane (1 ml), 3-(2-aminoethyl)-1H-indol-5-ol hydrochloride (128 mg, 0.603 mmol) and triethylamine (0.084 ml, 0.603 mmol), then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (10.2 mg, 13%, white solid).

<Example 30> Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(3-morpholinopropoxy)benzenesulfonamide

Step 1: Preparation of 4-(3-phenoxypropyl)morpholine

Phenol (600 mg, 6.38 mmol), 4-(3-hydroxypropyl)morpholine (1.11 g, 7.65 mmol) and triphenylphosphine (2.5 g, 9.56 mmol) were dissolved in tetrahydrofuran (16 ml), a solution of diethyl azodicarboxylate (DEAD) (4.34 ml, 9.56 mmol) was added dropwise, then stirred at room temperature for 12 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was removed under reduced pressure. The reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give 4-(3-phenoxypropyl)morpholine (1.41 g, 100%, clear oil).

Step 2: Preparation of 4-(3-morpholinopropoxy)benzene-1-sulfonyl chloride

4-(3-Phenoxypropyl)morpholine (1.41 g, 6.38 mmol) obtained in step 1 above was dissolved in dichloromethane (12 ml), chlorosulfonic acid (1.69 ml, 25, 5 mmol), then stirred at room temperature for 3 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with dichloromethane and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. This gave 4-(3-morpholinopropoxy)benzene-1-sulfonyl chloride (2.22 g, 67%, yellow solid) without further purification.

Step 3: Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(3-morpholinopropoxy)benzenesulfonamide

4-(3-Morpholinopropoxy)benzene-1-sulfonyl chloride (150 mg, 0.469 mmol) obtained in step 2 above was dissolved in dichloromethane (1.5 ml), 3-(1H-indol-3-yl) was added dropwise propan-1-amine (245 mg, 1.407 mmol) and potassium carbonate (194 mg, 1.407 mmol) were then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (10.6 mg, 5%, yellow solid).

<Example 31> Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 4-(3-bromopropoxy)benzene-1-sulfonyl chloride

(3-Bromopropoxy)benzene (1 g, 4.65 mmol) was dissolved in dichloromethane (15 ml), chlorosulfonic acid (1.236 ml, 18.60 mmol) was added dropwise at 0°C, then stirred at room temperature for 1 hour. After completion of the reaction, ice was added. The reaction mixture was extracted with dichloromethane and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The resulting 4-(3-bromopropoxy)benzene-1-sulfonyl chloride (1.1 g, 38%, yellow solid) was obtained without further purification.

Step 2: Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(3-bromopropoxy)benzenesulfonamide

4-(3-Bromopropoxy)benzene-1-sulfonyl chloride (538 mg, 1.716 mmol) obtained in step 1 above was dissolved in dichloromethane (5 ml), 3-(1H-indol-3-yl)propane was added dropwise -1-amine (897 mg, 5.15 mmol) and potassium carbonate (K ₂ CO ₃ ) (711 mg, 5.15 mmol) were then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give N-(3-(1H-indol-3-yl)propyl)-4-(3-bromopropoxy)benzenesulfonamide (230 mg, 29%, white solid).

Step 3: Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

N-(3-(1H-indol-3-yl)propyl)-4-(3-bromopropoxy)benzenesulfonamide (175 mg, 0.388 mmol) obtained in step 2 above was dissolved in ethanol (1.5 ml), added dropwise 1-methylpiperazine (0.172 ml, 1.551 mmol) and potassium carbonate (K ₂ CO ₃ ) (80 mg, 0.582 mmol), then stirred at 70°C for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (66 mg, 36%, white solid).

The compounds of examples 23-25 were prepared similarly to the method described in step 4 of example 1.

The compounds of examples 34 and 35 were prepared similarly to the method described in example 30.

The compound of example 36 was prepared similarly to the method described in example 31.

The compounds of examples 37-40 were prepared similarly to the method described in example 14.

The compounds of examples 41 and 42 were prepared similarly to the method described in example 30.

The compounds of examples 43-45 were prepared similarly to the method described in example 31.

<Example 46> Preparation of 4-(3-(dimethylamino)propoxy)-N-(3-(1-methyl-1H-indol-3-yl)propyl)benzenesulfonamide

Step 1: Preparation of N-(3-(1H-indol-3-yl)propyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide

N-(3-(1H-indol-3-yl)propyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide was prepared similarly to the method described in example 14.

Step 2: Preparation of 4-(3-(dimethylamino)propoxy)-N-(3-(1-methyl-1H-indol-3-yl)propyl)benzenesulfonamide

N-(3-(1H-indol-3-yl)propyl)-4-(3-(dimethylamino)propoxy)benzenesulfonamide (150 mg, 0.981 mmol) obtained in step 1 above was dissolved in DMF (1 ml), add sodium hydride (60%) (51.5 mg, 1.287 mmol) dropwise at -20°C, then stir for 30 minutes. At the same temperature, iodomethane (23 μL, 0.368 mmol) dissolved in DMF (0.1 mL) was slowly added dropwise, then stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and neutralized using a supersaturated aqueous ammonium chloride solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (13.7 mg, 8%, clear oil).

<Example 47> Preparation of N-(3-(1H-indol-3-yl)propyl)-4-bromobenzenesulfonamide

Step 1: Preparation of 4-bromobenzene-1-sulfonyl chloride

Bromobenzene (0.067 ml, 0.637 mmol) was dissolved in dichloromethane (2 ml), chlorosulfonic acid (0.169 ml, 2.55 mmol) was added dropwise at 0°C, then stirred at room temperature for 3 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with dichloromethane and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The resulting 4-bromobenzene-1-sulfonyl chloride (74 mg, 45%, white solid) was obtained without further purification.

Step 2: Preparation of N-(3-(1H-indol-3-yl)propyl)-4-bromobenzenesulfonamide

4-Bromobenzene-1-sulfonyl chloride (74 mg, 0.29 mmol) obtained in step 1 above in dichloromethane (1 ml) was added dropwise with 3-(1H-indol-3-yl)propan-1-amine (151 mg, 0.869 mmol) and potassium carbonate (K ₂ CO ₃ ) (120 mg, 0.869 mmol), then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (71 mg, 62%, white solid).

The compounds of examples 48-54 were prepared similarly to the method described in example 31.

The compound of Example 55 was prepared similarly to the method described in Example 30.

The compounds of examples 56-58 were prepared similarly to the method described in example 31.

The compounds of examples 59 and 60 were prepared similarly to the method described in example 30.

The compound of Example 61 was prepared similarly to the method described in Example 31.

The compound of Example 62 was prepared similarly to the method described in Example 30.

The compounds of examples 63-71 were prepared similarly to the method described in example 31.

<Example 72> Preparation of 4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl) benzenesulfonamide

Step 1: Preparation of (2S,6R)-tert-butyl 4-(3-(4-(N-(3-(5-fluoro-1H-indol-3-yl)propyl)sulfamoyl)phenoxy)propyl)-2 ,6-dimethylpiperazine-1-carboxylate

(2S,6R)-tert-butyl 4-(3-(4-(N-(3-(5-fluoro-1H-indol-3-yl)propyl)sulfamoyl)phenoxy)propyl)-2,6-dimethylpiperazine -1-carboxylate was prepared similarly to the method described in example 31.

Step 2: Preparation of 4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl)benzenesulfonamide

(2S,6R)-tert-butyl 4-(3-(4-(N-(3-(5-fluoro-1H-indol-3-yl)propyl)sulfamoyl)phenoxy)propyl)-2,6-dimethylpiperazine -1-carboxylate (80 mg, 0.133 mmol) obtained in step 1 above was dissolved in dichloromethane (1 ml), trifluoroacetic acid (0.2 ml, 2.65 mmol) was added at room temperature, then stirred at room temperature in within 3 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with ethyl acetate and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (5.2 mg, 7%, white solid).

The compounds of examples 73-76 were prepared similarly to the method described in example 31.

<Example 77> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-(methylamino)azetidin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of tert-butyl(1-(3-(4-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)phenoxy)propyl)azetidin-3-yl)( methyl)carbamate

Tert-butyl(1-(3-(4-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)phenoxy)propyl)azetidin-3-yl(methyl)carbamate was prepared similarly the method described in example 31.

Step 2: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-(methylamino)azetidin-1-yl)propoxy)benzenesulfonamide

Tert-butyl(1-(3-(4-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)phenoxy)propyl)azetidin-3-yl)(methyl)carbamate ( 38 mg, 0.064 mmol) was dissolved in dichloromethane (0.5 ml), using tert-butyl azetidin-3-yl(methyl)carbamate obtained in step 1 above, trifluoroacetic acid (0.2 ml, 2 .61 mmol), then stirred at room temperature for 2 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with ethyl acetate and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by HPLC to give the title compound (7 mg, 22%, yellow solid).

The compound of Example 78 was prepared similarly to the method described in Example 31.

<Example 79> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-6-(3-(piperazin-1-yl)propoxy)pyridin-3-sulfonamide

Step 1: Preparation of tert-butyl 4-(3-((5-bromopyridin-2-yl)oxy)propylpiperazine-1-carboxylate

5-Bromo-2-fluoropyridine (0.326 ml, 2.84 mmol) was dissolved in DMF (12 ml), sodium hydride 60% wt (0.159 g, 3.98 mmol) was added dropwise at 0°C, then stirred in within 5 minutes. Tert-butyl 4-(3-hydroxypropyl)piperazine-1-carboxylate was added dropwise, then stirred at 70°C for 6 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with dichloromethane and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The result was tert-butyl 4-(3-((5-bromopyridin-2-yl)oxy)propylpiperazine-1-carboxylate (1.35 g, 110%) without further purification.

Step 2: Preparation of tert-butyl 4-(3-((5-((4-methoxybenzyl)thio)pyridin-2-yl)oxy)propyl)piperazine-1-carboxylate

Tert-butyl 4-(3-((5-bromopyridin-2-yl)oxy)propyl piperazine-1-carboxylate (0.52 g, 1.3 mmol) obtained in step 1 above was dissolved in 1.4 -dioxane (12 ml), (4-methoxyphenyl)methanethiol (0.199 ml, 1.23 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.681 ml, 3.90 mmol) were added dropwise, then allowed to react for 5 minutes under nitrogen.Pd ₂ (dba) ₃ (9.91 mg, 0.032 mmol), Xantphos (0.038 g, 0.065 mmol) and tert-butyl-4-(3-hydroxypropyl)piperazine-1 were added dropwise -carboxylate, then allowed to react at 150 °C for 30 minutes in a Biotage microwave. After completion of the reaction, the reaction mixture was extracted with dichloromethane and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sulfate sodium and the solvent was removed under reduced pressure to obtain tert-butyl 4-(3-((5-((4-methoxybenzyl)thio)pyridin-2-yl)oxy)propyl)piperazine-1-carboxylate (0.51 g, 51.8%) without additional purification.

Step 3: Preparation of tert-butyl 4-(3-((5-(chlorosulfonyl)pyridin-2-yl)oxy)propyl)piperazine-1-carboxylate

Tert-butyl 4-(3-((5-((4-methoxybenzyl)thio)pyridin-2-yl)oxy)propyl)piperazine-1-carboxylate (0.469 g, 0.99 mmol) prepared in step 2 above , dissolved in acetic acid (8 ml) and water (2 ml), N-chlorosuccinimide (0.529 g, 3.96 mmol) was added dropwise, then allowed to react at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane and neutralized using a supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The result was tert-butyl 4-(3-((5-(chlorosulfonyl)pyridin-2-yl)oxy)propyl)piperazine-1-carboxylate (0.25 g, 60%) without further purification.

Step 4: Preparation of tert-butyl 4-(3-((5-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)pyridin-2-yl)oxy)propyl)piperazine -1-carboxylate

Tert-butyl 4-(3-((5-(chlorosulfonyl)pyridin-2-yl)oxy)propyl)piperazine-1-carboxylate (0.1 g, 0.238 mmol) obtained in step 3 above was dissolved in DMF ( 2 ml), 3-(5-chloro-1H-indol-3-yl)propan-1-amine (0.055 g, 0.262 mmol) and potassium carbonate (0.066 g, 0.476 mmol) were added dropwise, then stirred at room temperature within 2 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and neutralized using a supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by TLC to give tert-butyl 4-(3-((5-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)pyridin-2- yl)oxy)propyl)piperazine-1-carboxylate (18 mg, 12.8%).

Step 5: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-6-(3-(piperazin-1-yl)propoxy)pyridin-3-sulfonamide

4-(3-((5-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)pyridin-2-yl)oxy)propyl)piperazine-1-carboxylate (18 mg , 0.034 mmol) obtained in step 4 above was dissolved in tetrahydrofuran (1 ml), trifluoroacetic acid (0.5 ml, 6.49 mmol) was added dropwise at room temperature, then stirred at room temperature for 2 hours. After completion of the reaction, ice was added. The reaction mixture was extracted with ethyl acetate and neutralized using supersaturated sodium carbonate solution. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The reaction mixture was then separated and purified by TLC to give the title compound (4.5 mg, 30%).

The compounds of examples 80-84 were prepared similarly to the method described in example 31.

<Example 85> Preparation of N-(3-(1H-indol-3-yl)cyclohexyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 3-(1H-indol-3-yl)cyclohexan-1-one

1H-indole (1 g, 8.54 mmol) and cyclohex-2-enone (1.64 g, 17.1 mmol) were dissolved in CH ₃ CN (30 ml), Sc(OTf) ₃ (0.42 g) was added , 0.854 mmol), then stirred at 30°C for 3 hours under N ₂ atmosphere. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified using rep. HPLC to obtain the target compound (805 mg, 44%).

Step 2: Preparation of 3-(1H-indol-3-yl)cyclohexane-1-amine

3-(1H-indol-3-yl)cyclohexan-1-one (800 mg, 3.75 mmol) obtained in step 1 above was dissolved in dichloroethane (10 ml) and acetic acid (0.5 ml), at Ammonium acetate (8.67 g, 113 mmol) was added at room temperature, then stirred for 2 hours. Sodium triacetoxyborohydride (3.18 g, 15.0 mmol) was then added at room temperature, followed by stirring for 5 hours. After completion of the reaction, the reaction mixture obtained by concentrating the mixture under reduced pressure was separated and purified by HPLC to obtain the target compound (250 mg, 31%, yellow solid).

Step 3: Preparation of N-(3-(1H-indol-3-yl)cyclohexyl)-4-(3-bromopropoxy)benzenesulfonamide

The title compound (100 mg, 46%, white solid) was prepared analogously to the method described in step 2 of Example 31 using 3-(1H-indol-3-yl)cyclohexan-1-amine (105 mg, 0.491 mmol), obtained in step 2 above, and 4-(3-bromopropoxy)benzenesulfonyl chloride (140 mg, 0.446 mmol) prepared in a similar manner to the method described in step 2 of Example 31.

Step 4: Preparation of N-(3-(1H-indol-3-yl)cyclohexyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The title compound (21.6 mg, 69% yield) as a white solid is similar to the method described in step 3 of Example 31 using N-(3-(1H-indol-3-yl)cyclohexyl)-4-(3 -bromopropoxy)benzenesulfonamide (30 mg, 0.061 mmol) obtained in step 3 above, and 1-methylpiperazine (24.5 mg, 0.244 mmol).

<Example 86> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)naphthalene-1-sulfonamide

Step 1: Preparation of sodium (I) salt of 4-(3-bromopropoxy)naphthalene-1-sulfonate

4-Hydroxynaphthalene-1-sulfonate, sodium (I) salt (0.3 g, 1.218 mmol) was dissolved in ethanol (2.5 ml), 1,3-dibromopropane (0.211 ml, 2.071 mmol), tetrabutylammonium sulfate (0.033) was added g, 0.097 mmol) and aqueous potassium hydroxide (1.56 ml, 1.218 mmol), then refluxed for 3 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, redissolved in ethanol, and concentrated again. After hot methanol was added to the reaction solution, the insoluble matter was filtered and the filtrate was concentrated. The resulting solid was washed with dichloromethane and filtered to give the title compound (0.4 g, 99%, white solid).

Step 2: Preparation of 4-(3-bromopropoxy)naphthalene-1-sulfonyl chloride

To the compound (0.2 g, 0.545 mmol) obtained in step 1 above, thionyl chloride (0.286 ml, 3.92 mmol) and dimethylformamide (1.91 μl) were added, then refluxed for 4 hours. After completion of the reaction, the temperature was lowered to room temperature, and the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and used in the next step without further purification.

Step 3: Preparation of 4-(3-bromopropoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)naphthalene-1-sulfonamide

The target compound was prepared analogously to the method described in step 2 of example 31.

Step 4: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)naphthalene-1-sulfonamide

The target compound was prepared analogously to the method described in step 3 of example 31.

The compound of Example 87 was prepared similarly to the method described in Example 31.

<Example 88> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-4-yl)propyl)amino)benzenesulfonamide

Step 1: Preparation of tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate

Tert-butyl-4-(3-hydroxypropyl)piperidine-1-carboxylate (0.3 g, 1.233 mmol) was dissolved in dichloromethane (6 ml), Dess-Martin periodinane (0.680 g, 1.603 mmol) was added at 0°C. , then stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was filtered, and the filtrate was washed with an aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by HPLC to give the title compound (0.24 g, 79%, clear oil).

Step 2: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-nitrobenzenesulfonamide

The target compound was prepared analogously to the method described in step 2 of example 31.

Step 3: Preparation of 4-amino-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide

The compound (0.72 g, 1.840 mmol) obtained in step 2 above was dissolved in ethyl acetate (12 ml), tin(II) chloride dihydrate (4.15 g, 18.40 mmol) was added, then heated at 60° C for 5 hours. After completion of the reaction, ammonia water was added to the reaction solution to adjust the pH to 5, and sodium carbonate was added to adjust the pH to 7. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure, which was used in the next step without further purification.

Step 4: Preparation of tert-butyl 4-(3-((4-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)phenyl)amino)propyl)piperidine-1-carboxylate

The compound (0.05 g, 0.137 mmol) obtained in step 3 above was dissolved in dichloroethane (1 ml), the compound (0.046 g, 0.192 mmol) obtained in step 1 above was added and acetic acid (0.024 ml, 0.412 mmol ), then stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.087 g, 0.412 mmol) was added, then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine. The remainder of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, purified using rep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.017 g, 5%, yellow solid).

Step 5: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-4-yl)propyl)amino)benzenesulfonamide

The target compound was prepared analogously to the method described in step 5 of example 79.

<Example 89> Preparation of N-(3-(1H-indol-3-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 3-(3-nitrophenyl)-1H-indole

N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide and 1-iodo-3-nitrobenzene were dissolved in DMSO, treated with an excess amount of K ₂ CO ₃ in the presence of a catalytic amount of Pd ₂ (dba) ₃ to obtain the target compound 3- (3-nitrophenyl-1H-indole).

Step 2: Preparation of 3-(1H-indol-3-yl)aniline

The compound (0.047 g, 0.197 mmol) obtained in step 1 above was dissolved in methanol (2 ml), Pd/C (0.004 g, 3.76 μmol) was added, then stirred at room temperature for 3 hours under a hydrogen atmosphere. After completion of the reaction, the reaction solution was filtered through celite and washed with methanol. The filtrate was concentrated under reduced pressure and used in the next step without further purification.

Step 3: Preparation of N-(3-(1H-indol-3-yl)phenyl)-4-(3-bromopropoxy)benzenesulfonamide

The compound (0.041 g, 0.197 mmol) obtained in step 2 above was dissolved in pyridine (1 ml), the compound (0.068 g, 0.217 mmol) obtained in step 1 of Example 31 was added at 0°C, then stirred at room temperature within 3 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated and purified by HPLC to give the title compound (0.047 g, 49%, yellow solid).

Step 4: Preparation of N-(3-(1H-indol-3-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The target compound was prepared analogously to the method described in step 3 of example 31.

<Example 90> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-1-yl)butyl)benzenesulfonamide

Step 1: Preparation of 4-(4-bromobutyl)benzene-1-sulfonyl chloride

The title compound (1.4 g, 96%, white solid) was prepared analogously to the method described in step 1 of Example 31 using (4-bromobutyl)benzene (1.0 g, 4.69 mmol) and chlorosulfonic acid (0.936 ml, 14.1 mmol).

Step 2: Preparation of 4-(4-bromobutyl)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonylamide

4-(4-Bromobutyl)benzene-1-sulfonyl chloride (300 mg, 0.963 mmol) obtained in step 1 above was dissolved in dichloromethane (5 ml), 3-(5-chloro-1H-indole-3) was added at room temperature -yl)propan-1-amine (211 mg, 1.01 mmol) and triethylamine (0.268 ml, 1.93 mmol) were then stirred for 3 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and purified by HPLC to give the title compound (330 mg, 71%, white solid).

Step 3: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-1-yl)butyl)benzenesulfonamide

The title compound (16 mg, 53%, white solid) was prepared analogously to the method described in step 3 of Example 31 using 4-(4-bromobutyl)-N-(3-(5-chloro-1H-indole-3 -yl)propyl)benzenesulfonylamide (30 mg, 0.062 mmol) obtained in step 2 above, piperidine (15.9 mg, 0.186 mmol) and potassium carbonate (12.9 mg, 0.093 mmol).

The compound of Example 91 was prepared similarly to the method described in Example 90.

<Example 92> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzenesulfonamide

Step 1: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-hydroxybenzenesulfonamide

4-Hydroxybenzene-1-sulfonyl chloride (0.5 g, 2.60 mmol) was dissolved in dichloromethane (8.7 ml), 3-(5-chloro-1H-indol-3-yl)propan-1-amine was added ( 0.596 g, 2.86 mmol) and triethylamine (0.724 ml, 5.19 mmol), then stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and then purified by HPLC to give the title compound (0.19 g, 21%, white solid).

Step 2: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzenesulfonamide

The compound (0.05 g, 0.137 mmol) obtained in step 1 above was dissolved in tetrahydrofuran (1.5 ml) under nitrogen atmosphere at 0°C, 3-(1-methylpiperidin-4-yl)propan-1 was added -ol (0.026 g, 0.164 mmol), PPh ₃ (0.054 g, 0.206 mmol) and DEAD (0.093 ml, 0.206 mmol), then stirred for 1 hour. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine. The remainder of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, purified using rep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.004 g, 7%, white solid).

<Example 93> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-4-yl)propoxy)benzenesulfonamide

The compound (0.035 g, 0.061 mmol) obtained in the same manner as described in Example 92 was dissolved in dichloromethane (2 ml), trifluoroacetic acid (1 ml, 12.98 mmol) was added, then stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified using rep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.01 g, 37%, white solid).

The compound of Example 94 was prepared similarly to the method described in Example 93.

The compounds of Examples 95 and 96 were prepared similarly to the method described in Example 94.

The compound of Example 97 was prepared similarly to the method described in Example 31.

<Example 98> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methylpiperazin-1-yl)propyl)amino)benzenesulfonamide

The compound (0.05 g, 0.136 mmol), obtained analogously to the method described in step 2 of example 47, was dissolved in dimethylformamide (1 ml), 3-(4-methylpiperazin-1-yl)propan-1-amine (0.043 g) was added , 0.273 mmol) and potassium carbonate (0.021 g, 0.150 mmol), then stirred at 100°C for 3 days. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified using rep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.01 g, 16%, white solid).

<Example 99> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-4-yl)butyl)benzenesulfonamide

Step 1: Preparation of tert-butyl 4-(but-3-en-1-yl)piperidin-1-carboxylate

Methyltriphenylphosphonium bromide (1.184 g, 3.32 mmol) was dissolved in anhydrous tetrahydrofuran (2 ml), lithium bistrimethylsilylamide (3.32 ml, 3.32 mmol) was slowly added at 0°C. After dissolution at 0°C, tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate (0.4 g, 1.66 mmol) obtained in step 1 of Example 88 in anhydrous tetrahydrofuran (2 ml). The mixture was stirred at 0°C for 30 minutes and then stirred at room temperature for 20 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, washed with brine, and extracted with ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure and purified by HPLC to give the title compound (0.2 g, 50%, clear oil).

Step 2: Preparation of tert-butyl 4-(4-(4-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)phenyl)butyl)piperidine-1-carboxylate

Tert-butyl 4-(but-3-en-1-yl)piperidin-1-carboxylate (50 mg, 0.209 mmol) obtained in step 2 above was dissolved in anhydrous tetrahydrofuran (1.5 ml), added at room temperature 9-borabicyclo[3,3,1]nonane (0.796 ml, 0.398 mmol). The reaction mixture was gradually heated and stirred at reflux for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was dissolved in 1,4-dioxane (1.5 ml), 4-bromo-N-(3-(5-chloro-1H-indol-3)-yl)propyl)benzenesulfonamide (85 mg, 0.199 mmol) was added. , prepared similarly to the method described in step 2 of Example 90, and 1 M aqueous sodium carbonate solution (0.597 ml, 0.597 mmol). Pd(PPh ₃ ) ₄ (23 mg, 0.02 mmol) was added to the reaction mixture and the mixture was gradually heated and stirred at 90 °C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered through celite, concentrated under reduced pressure and purified using Rev. HPLC to obtain the title compound (15 mg, 13%, yellow solid).

Step 3: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-4-yl)butyl)benzenesulfonamide

Tert-butyl 4-(4-(4-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)phenyl)butyl)piperidine-1-carboxylate (15 mg, 0.013 mmol) , obtained in step 2 above, was dissolved in dichloromethane (2 ml), trifluoroacetic acid (1 ml, 13.1 mmol) was added at room temperature, then stirred for 1 hour. After completion of the reaction, the residue obtained by concentrating the mixture was neutralized with a supersaturated aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate. The extracted organic layer was washed with distilled water, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to obtain the target compound (5 mg, 56%, white solid).

The compounds of examples 100-102 were prepared similarly to the method described in example 31.

<Example 103> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 1-(3-bromopropoxy)-2-fluorobenzene

2-Fluorophenol (5 g, 44.6 mmol) was dissolved in acetonitrile (74 ml), 1,3-dibromopropane (90 g, 446 mmol) and potassium carbonate (6.16 g, 44.6 mmol) were added, then stirred at 80°C for 16 hours. After completion of the reaction, the reaction solution was filtered, concentrated under reduced pressure and used in the next step without further purification.

Step 2: Preparation of 4-(3-bromopropoxy)-3-fluorobenzenesulfonyl chloride

The compound (5 g, 19.31 mmol) obtained in step 1 above was dissolved in dichloromethane (38 ml), chlorosulfonic acid (5.13 ml, 77 mmol) was added, then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was diluted with dichloromethane and neutralized with aqueous sodium carbonate at 0°C. The remainder of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and used in the next step without further purification.

Step 3: Preparation of 4-(3-bromopropoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluorobenzenesulfonamide

The compound (1 g, 3.02 mmol) obtained in step 2 above was dissolved in dichloromethane (6 ml), 3-(5-chloro-1H-indol-3-yl)propan-1-amine (0.818 g, 3.92 mmol) and potassium carbonate (0.542 g, 3.92 mmol), then stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane, and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated and then purified by HPLC to give the title compound (1.1 g, 77%, white solid).

Step 4: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The compound (0.05 g, 0.099 mmol) obtained in step 3 above was dissolved in ethanol (1 ml), potassium carbonate (0.021 g, 0.149 mmol) and 1-methylpiperazine (0.020 g, 0.198 mmol) were added, then stirred at temperature 70°C for 16 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine. The remainder of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, purified using rep. HPLC and then neutralized by adding aqueous sodium hydrogen carbonate to obtain the title compound (0.011 g, 22%, white solid).

The compounds of examples 104-106 were prepared similarly to the method described in example 103.

<Example 107> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The title compound (15 mg, 72%) was obtained as a pale yellow solid similar to the method described in step 4 of Example 99 using tert-butyl 4-(3-(4-(N-(3-(5- chloro-1H-indol-3-yl)propyl)sulfamoyl)phenoxy)propyl)-2-methylpiperazine-1-carboxylate (25 mg, 0.041 mmol), prepared analogously to the method described in example 31, and trifluoroacetic acid (1 ml, 13.1 mmol).

The compounds of examples 108-111 were prepared similarly to the method described in example 107.

Example 112 was prepared similarly to the method described in Example 90.

<Example 113> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperazin-1-yl)propyl)amino)benzenesulfonamide

The compound (0.0142 g, 0.024 mmol) obtained in the same manner as described in Example 98 was dissolved in dichloromethane (2 ml), trifluoroacetic acid (1 ml, 12.98 mmol) was added, then stirred at room temperature for 1 hour . After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified using rep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.005 g, 50%, white solid).

The compound of Example 114 was prepared similarly to the method described in Example 98.

The compound of Example 115 was prepared analogously to the method described in steps 1-3 of Example 99.

<Example 116> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-((4-methylpiperazin-1-yl)methyl)cyclopropyl)methoxy)-benzenesulfonamide

Step 1: Preparation of (1-(((tert-butyldimethylsilyl)oxy)-methyl)cyclopropyl)methanol

Cyclopropane-1,1-diyldimethanol (5 g, 49.0 mmol) was dissolved in dichloromethane (130 mL), imidazole (5 g, 73.4 mmol) and tert-butyldimethylsilyl chloride (7.75 g, 51.4 mmol) were added. . The reaction mixture was stirred at 0°C for 30 minutes and then stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was neutralized with a supersaturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extracted organic layer was washed with distilled water, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure. The reaction mixture was purified by HPLC to give the title compound (4.7 g, 44%, clear oil).

Step 2: Preparation of ((1-(bromomethyl)cyclopropyl)methoxy)-(tert-butyl)dimethylsilane

(1-(((T-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol (1.1 g, 5.08 mmol) obtained in step 1 above was dissolved in dichloromethane (10 ml), carbon tetrabromide (1.85) was added g, 5.59 mmol) and triphenylphosphine (1.47 g, 5.59 mmol). The reaction mixture was stirred at 0°C for 30 minutes and then stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and purified by HPLC to give the title compound (1 g, 70%, clear oil).

Step 3: Preparation of (1-(bromomethyl)cyclopropyl)methanol

((1-(Bromomethyl)cyclopropyl)methoxy)(tert-butyl)dimethylsilane (1 g, 3.58 mmol) obtained in step 2 above was dissolved in acetic acid/tetrahydrofuran/distilled water (12 ml/4 ml/4 ml), then stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was neutralized with a supersaturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extracted organic layer was washed with distilled water, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure. The resulting reaction mixture was purified by HPLC to give the title compound (0.3 g, 51%, yellow oil).

Step 4: Preparation of 4-((1-(bromomethyl)cyclopropyl)methoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide

The title compound (45 mg, 48%, yellow solid) was prepared analogously to the method described in step 2 of Example 92 using (1-(bromomethyl)cyclopropyl)methanol (30 mg, 0.182 mmol) obtained in step 3 above, N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-hydroxybenzenesulfonamide (66 mg, 0.182 mmol), triphenylphosphine (72 mg, 0.273 mmol) and diethyl azodicarboxylate (0.124 ml, 0.273 mmol) .

Step 5: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-((4-methylpiperazin-1-yl)methyl)cyclopropyl)methoxy)-benzenesulfonamide

The title compound (12.3 mg, 59%, yellow solid) was prepared analogously to the method described in step 3 of Example 31 using 4-((1-(bromomethyl)cyclopropyl)methoxy)-N-(3-(5 -chloro-1H-indol-3-yl)propyl)benzenesulfonamide (20 mg, 0.039 mmol) obtained in step 4 above, 1-methylpiperazine (0.013 ml, 0.117 mmol) and potassium carbonate (8.1 mg, 0.059 mmol) .

The compound of Example 117 was prepared similarly to the method described in Example 116.

<Example 118> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)phenoxy)benzenesulfonamide

Step 1: Preparation of 4-(3-bromophenoxy)benzenesulfonic acid

1-Bromo-3-phenoxybenzene (300 mg, 1.20 mmol) was dissolved in dichloromethane, and chlorosulfonic acid (0.088 ml, 1.33 mmol) was added slowly at 0°C. The reaction mixture was stirred at 0°C for 30 minutes and then stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain the target compound (395 mg, 100%, yellow oil).

Step 2: Preparation of 4-(3-bromophenoxy)benzenesulfonyl chloride

4-(3-Bromophenoxy)benzenesulfonic acid (395 mg, 1.20 mmol) obtained in step 1 above was dissolved in SnCl ₂ ⋅H ₂ O (3 ml, 41.4 mmol) at 0°C, then stirred . Two drops of diformamide were then added at 0°C and the reaction mixture was gradually heated and stirred at reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, concentrated under reduced pressure and purified by HPLC to give the title compound (380 mg, 91%, yellow oil).

Step 3: Preparation of 4-(3-bromophenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide

The title compound (170 mg, 76%, yellow solid) was prepared analogously to the method described in step 2 of Example 90 using 4-(3-bromophenoxy)benzenesulfonyl chloride (150 mg, 0.432 mmol) obtained in step 2 above , 3-(5-chloro-1H-indol-3-yl)propan-1-amine (90 mg, 0.432 mmol) and triethylamine (0.090 ml, 0.647 mmol).

Step 4: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)phenoxy)benzenesulfonamide

4-(3-Bromophenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide (90 mg, 0.173 mmol) obtained in step 3 above was dissolved in 1,4-dioxane (1.5 ml), tert-BuOK (29.1 mg, 0.260 mmol) and 1-methylpiperazine (0.03 ml, 0.260 mmol) were added at room temperature. The reaction mixture was heated at 70°C with stirring and degassed for 5 minutes using nitrogen from a cylinder, Pd(t-Bu ₃ P) ₂ (8 mg, 0.016 mmol) was added, then stirred at reflux for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered and concentrated through celite and purified using Rev. HPLC. The resulting trifluoroacetate compound was neutralized by adding a supersaturated aqueous sodium hydrogen carbonate solution and extracted with a 10% methanol/dichloromethane solution. The organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to obtain the title compound (6.5 mg, 53%, white solid).

The compound of Example 119 was prepared similarly to the method described in steps 1-3 of Example 118.

The compounds of examples 120-122 were prepared similarly to the method described in example 118.

<Example 123> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methylpiperazin-1-yl)phenyl)amino)benzenesulfonamide

The compound (0.05 g, 0.117 mmol), obtained analogously to the method described in step 2 of example 47, was dissolved in 2-butanol (1.5 ml), 3-(4-methylpiperazin-1-yl)aniline (0. 02 g, 0.117 mmol) and potassium carbonate (0.08 g, 0.584 mmol), then degassed for 1 minute. Pd ₂ (dba) ₃ (0.01 g, 0.012 mmol) and Xphos (0.005 g, 0.012 mmol) were then added at 80°C and stirred at 100°C for 1 hour. After completion of the reaction, the reaction solution was filtered through celite and washed with ethyl acetate and dichloromethane. The filtrate was concentrated under reduced pressure and purified using prep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.023 g, 37%, yellow solid).

The compounds of examples 124-127 were prepared similarly to the method described in example 123.

The compounds of Examples 128 and 129 were prepared similarly to the method described in Example 119.

<Example 130> Preparation of 4-(3,5-bis(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide

Step 1: Preparation of 1,3-dibromo-5-phenoxybenzene

Phenol (100 mg, 1.06 mmol) was dissolved in N-methyl-2-pyrrolidinone (2 ml), cesium carbonate (173 mg, 0.531 mmol), 1,3-dibromo-5-fluorobenzene (0.201 ml) was added at room temperature , 1.59 mmol), TMHDA (0.057 ml, 0.266 mmol) and CuCl (52.6 mg, 0.531 mmol). The reaction mixture was degassed at room temperature using nitrogen from a cylinder, then stirred for 20 minutes. The reaction mixture was gradually heated and stirred at 120°C for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered through celite, extracted with ethyl acetate and concentrated under reduced pressure. The resulting reaction mixture was purified by HPLC to give the title compound (220 mg, 63%, yellow solid).

Step 2: Preparation of 4-(3,5-dibromophenoxy)benzenesulfonic acid

The title compound (274 mg, 100%, yellow solid) was prepared analogously to the method described in step 1 of Example 118, using 1,3-dibromo-5-phenoxybenzene (220 mg, 0.671 mmol) obtained in step 1 above, and chlorosulfonic acid (0.049 ml, 0.738 mmol).

Step 3: Preparation of 4-(3,5-dibromophenoxy)benzenesulfonyl chloride

The title compound (230 mg, 80%, yellow solid) was prepared analogously to the method described in step 2 of Example 118 using 4-(3,5-dibromophenoxy)benzenesulfonic acid (274 mg, 0.671 mmol) obtained in step 2 above, and thionyl chloride (4 ml, 55.1 mmol).

Step 4: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3,5-dibromophenoxy)benzenesulfonamide

The title compound (300 mg, 93%, white solid) was prepared analogously to the method described in step 2 of Example 90 using 4-(3,5-dibromophenoxy)-benzenesulfonyl chloride (230 mg, 0.539 mmol) obtained in step 3 above, 3-(5-chloro-1H-indol-3-yl)propan-1-amine (118 mg, 0.566 mmol) and triethylamine (0.113 ml, 0.809 mmol).

Step 5: Preparation of 4-(3,5-bis(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide

The title compound (5 mg, 9%, yellow solid) was prepared analogously to the method described in step 4 of Example 118 using N-(3-(5-chloro-1H-indol-3-yl)propyl)-4- (3,5-dibromophenoxy)benzenesulfonamide (50 mg, 0.084 mmol) obtained in step 4 above, 1-methylpiperazine (0.037 ml, 0.334 mmol), potassium tert-butoxide (37.5 mg, 0.334 mmol) and Pd(t -Bu ₃ P) ₂ (8.54 mg, 0.017 mmol).

The compounds of examples 131-134 were prepared similarly to the method described in example 123.

The compounds of Examples 135 and 136 were prepared similarly to the method described in Example 118.

The compound of Example 137 was prepared similarly to the method described in Example 138.

<Example 138> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-bromo-5-(4-methylpiperazin-1-yl)phenoxy)benzenesulfonamide

Step 1: Preparation of 1-bromo-3-fluoro-5-phenoxybenzene

The title compound (0.45 g, 32%, clear oil) was prepared analogously to the method described in step 1 of Example 130 using phenol (0.5 g, 5.31 mmol), cesium carbonate (0.866 g, 2.66 mmol ), 1-bromo-3,5-difluorobenzene (1.54 g, 7.97 mmol), TMHDA (0.284 ml, 1.33 mmol) and CuCl (0.263 mg, 2.66 mmol).

Step 2: Preparation of 4-(3-bromo-5-fluorophenoxy)benzene-1-sulfonyl chloride

The title compound (0.44 g, 71%, yellow oil) was prepared analogously to the method described in step 1 of Example 31 using 1-bromo-3-fluoro-5-phenoxybenzene (0.45 g, 1.685 mmol) obtained in step 1 above, and chlorosulfonic acid (0.123 ml, 1.853 mmol).

Step 3: Preparation of 4-(3-bromo5-fluorophenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide

The title compound (300 mg, 93%, yellow solid) was prepared analogously to the method described in step 2 of Example 90 using 4-(3-bromo-5-fluorophenoxy)benzene-1-sulfonyl chloride (200 mg, 0.547 mmol) from step 2 above, 3-(5-chloro-1H-indol-3-yl))propan-1-amine (115 mg, 0.553 mmol) and triethylamine (0.114 mL, 0.821 mmol).

Step 4: Preparation of 4-(3-bromo-5-(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide

4-(3-Bromo-5-fluorophenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide (30 mg, 0.056 mmol) obtained in step 3 above was dissolved in dimethyl sulfoxide (1 ml), 1-methylpiperazine (0.025 ml, 0.223 mmol) and potassium carbonate (30.8 mg, 0.223 mmol) were added at room temperature. The reaction mixture was then heated at 120°C and stirred for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, washed with distilled water and brine, and extracted with ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure and purified using rep. HPLC. The resulting trifluoroacetate compound was neutralized by adding a supersaturated aqueous sodium hydrogen carbonate solution, then extracted with a 10% methanol/dichloromethane solution. The extracted organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to obtain the title compound (6.2 mg, 22%, ivory solid).

The compounds of examples 139-142 were prepared similarly to the method described in example 123.

<Example 143> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzamide

Step 1: Preparation of methyl 4-(3-bromopropoxy)benzoate

Methyl 4-hydroxybenzoate (0.5 g, 3.29 mmol) was dissolved in acetonitrile (10 ml), 1,3-dibromopropane (0.995 g, 4.93 mmol) and potassium carbonate (0.681 g, 4.93 mmol) were added. . The reaction mixture was heated at 80°C and stirred for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered through celite, and concentrated under reduced pressure. The resulting residue was purified by HPLC to give the title compound (0.7 g, 78%, clear oil).

Step 2: Preparation of 4-(3-bromopropoxy)benzoic acid

Methyl 4-(3-bromopropoxy)benzoate (0.7 g, 2.56 mmol) obtained in step 1 above was dissolved in tetrahydrofuran/methanol/distilled water (6.0 ml/3 ml/3 ml), at LiOH·H ₂ O (0.323 g, 7.69 mmol) was added at room temperature. The reaction mixture was then heated at 50°C and stirred for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and 1N aqueous hydrochloric acid solution was slowly added dropwise until the pH reached 2. The resulting solid was washed with distilled water and then dried in vacuo to give the title compound (0.35 g, 53%, white solid colors).

Step 3: Preparation of 4-(3-bromopropoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzamide

4-(3-Bromopropoxy)benzoic acid (0.1 g, 0.386 mmol) obtained in step 2 above was dissolved in dichloromethane (2 ml), 3-(5-chloro-1H-indole-3- yl)propan-1-amine (0.081 g, 0.390 mmol), HATU (0.294 g, 0.772 mmol) and N,N-diisopropylethylamine (0.15 g, 1.158 mmol) were then stirred at room temperature for 16 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with dichloromethane. The extracted organic layer was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure and purified by HPLC to give the title compound (0.1 g, 58%, ivory solid).

Step 4: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzamide

The title compound (8 mg, 38%, ivory solid) was prepared analogously to the method described in step 3 of Example 31 using 4-(3-bromopropoxy)-N-(3-(5-chloro-1H-indol- 3-yl)propyl)benzamide (20 mg, 0.044 mmol) obtained in step 3 above, 1-methylpiperazine (0.02 ml, 0.178 mmol) and potassium carbonate (12.3 mg, 0.089 mmol).

The compound of Example 144 was prepared similarly to the method described in Example 143.

The compound of Example 145 was prepared similarly to the method described in Example 92.

<Example 146> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-2-((3-(piperazin-1-yl)propyl)amino)triazole-5-sulfonamide

Step 1: Preparation of 2-chloro-N-(3-(5-chloro-1H-indol-3-yl)propyl)triazole-5-sulfonamide

The target compound was prepared analogously to the method described in step 2 of example 31.

Step 2: Preparation of tert-butyl 4-(3-((5-(N-(3-(5-chloro-1H-indol-3-yl)propyl)sulfamoyl)thiazol-2-yl)amino)propyl)piperazine -1-carboxylate

2-Chloro-N-(3-(5-chloro-1H-indol-3-yl)propyl)triazole-5-sulfonamide (30 mg, 0.077 mmol) obtained in step 1 above was dissolved in dimethylformamide, tert- butyl 4-(3-aminopropyl)piperazine-1-carboxylate (28 mg, 0.115 mmol) and DIPEA (0.022 ml, 0.154 mmol). The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed under reduced pressure and then the reaction mixture was separated and purified by HPLC to obtain the target compound (37 mg, 81%, yellow solid).

Step 3: Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-2-((3-(piperazin-1-yl)propyl)amino)triazole-5-sulfonamide

The title compound (30 mg, 97%, pale yellow solid) was prepared analogously to the method described in step 3 of example 99.

<Example 147> Preparation of N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 3-(5-chloro-2-methyl-1H-indol-3-yl)propan-1-amine hydrochloride

Chlorophenyl hydrazine (1.40 g, 9.81 mmol) and 6-chlorohexan-2-one (1.10 g, 8.17 mmol) were dissolved in ethanol (30 ml), then stirred at reflux for 20 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure to obtain 3-(5-chloro-2-methyl-1H-indol-3-yl)propan-1-amine hydrochloride (2.114 g, quantitative, pale solid -yellow color).

Step 2: Preparation of 4-(3-bromopropoxy)-N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)benzenesulfonamide

3-(5-Chloro-2-methyl-1H-indol-3-yl)propan-1-amine hydrochloride (0.413 g, 1.59 mmol) obtained in step 1 above was dissolved in ethylene chloride (6 ml), added triethylamine (0.444 mL, 3.19 mmol) dropwise, then stirred for 5 minutes. 4-(3-bromopropoxy)benzene-1-sulfonyl chloride (0.200 g, 0.638 mmol) was added dropwise, then stirred at room temperature for 1 hour. To complete the reaction, water was added dropwise, then extracted with dichloromethane. The extracted organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was removed under reduced pressure. The mixture was then separated and purified by HPLC to give the title compound (177 mg, 56%, brown solid).

Step 3: Preparation of N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The title compound (19.8 mg, 64%, pale yellow solid) was prepared analogously to the method described in step 3 of example 31.

<Example 148> Preparation of N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

4-(4-Bromobutyl)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide (30 mg, 0.062 mmol) obtained in step 2 of Example 90 was dissolved in acetonitrile, at room potassium carbonate (25.7 mg, 0.186 mmol) and 1H-imidazole (8.44 mg, 0.124 mmol) were added, then stirred at 60°C for 4 hours. After completion of the reaction, the mixture was filtered through celite. The filtrate was concentrated under reduced pressure and then separated and purified by HPLC to give the title compound (13 mg, 45%, white solid).

<Example 149> Preparation of N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 2-((5-chloro-1H-indol-3-yl)methyl)aniline

5-Chloro-1H-indole (1 g, 6.60 mmol) and (2-aminophenyl)methanol (0.812 g, 6.60 mmol) were dissolved in 1,2-dichloroethane (20 ml), trifluoroacetic acid was added at room temperature (0.151 ml, 1.979 mmol), then stirred at 50°C for 16 hours. After cooling the mixture to room temperature, supersaturated aqueous sodium carbonate was added dropwise to complete the reaction, then extracted with ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, filtered and then separated and purified by HPLC to give the title compound (0.55 g, 33%, yellow solid).

Step 2: Preparation of 4-(3-bromopropoxy)-N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)benzenesulfonamide

The target compound was prepared analogously to the method described in step 2 of example 31.

Step 3: Preparation of N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The title compound (13.2 mg, 64%, pale yellow solid) was prepared similarly to the method described in Example 148.

The compound of Example 150 was prepared similarly to the method described in Example 149.

<Example 151> Preparation of N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 4-((5-chloro-1H-indol-3-yl)butan-2-one

5-Chloro-1H-indole (1 g, 6.60 mmol) was dissolved in distilled water (20 ml), 3-buten-2-one (1.387 g, 19.79 mmol) and trifluoromethanesulfonic acid (10) were added at room temperature mg, 0.066 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was washed with a supersaturated aqueous sodium carbonate solution and then extracted with ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, filtered and then separated and purified by HPLC to give the title compound (0.64 g, 44%, pale yellow solid).

Step 2: Preparation of 4-(5-chloro-1H-indol-3-yl)butan-2-amine

4-((5-Chloro-1H-indol-3-yl)butan-2-one (200 mg, 0.902 mmol) obtained in step 1 above was dissolved in methanol (8 ml), ammonium acetate was added at room temperature ( 695 mg, 9.02 mmol) and sodium cyanoborohydride (283 mg, 4.51 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was washed with a supersaturated aqueous solution of sodium carbonate and then extracted with ethyl acetate. Extracted organic layer dried over anhydrous sodium sulfate, filtered and separated and purified by HPLC to give the title compound (0.2 g, 100%, pale yellow oil).

Step 3: Preparation of 4-(3-bromopropoxy)-N-(4-(5-chloro-1H-indol-3-yl)butan-2-yl)benzenesulfonamide

The target compound was prepared analogously to the method described in step 2 of example 31.

Step 4: Preparation of N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The target compound (16 mg, 77%, white solid) was prepared analogously to the method described in Example 149.

The compound of Example 152 was prepared similarly to the method described in Example 151.

<Example 153> Preparation of N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of 3-(5-bromo-1H-indol-3-yl)propan-1-ol

(4-Bromophenyl)hydrazine hydrochloride (1 g, 4.47 mmol) was dissolved in acetonitrile (10 ml), 4% aqueous sulfuric acid (10 ml) was added. 3,4-dihydro-2H-pyran (0.40 mL, 4.47 mmol) was added slowly at 100°C over 2 minutes, then stirred at 100°C for 2 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and then purified by HPLC to give the title compound (0.61 g, 54%).

Step 2: Preparation of 5-bromo-3-(3-bromopropyl)-1H-indole

The compound (0.31 g, 1.231 mmol) obtained in step 1 above was dissolved in dichloromethane (2 ml), carbon tetrabromide (0.49 g, 1.477 mmol) and triphenylphosphine (0.38 g, 1.477 mmol). The reaction mixture was stirred for 30 minutes and then stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and then purified by HPLC to obtain the target compound (0.29 g, 77%).

Step 3: Preparation of 3-(3-azidopropyl)-5-bromo-1H-indole

The compound (0.99 g, 3.25 mmol) obtained in step 2 above was dissolved in dimethylformamide (11 ml), sodium azide (1.05 g, 16.24 mmol) was added, then stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and then purified by HPLC to give the title compound (0.54 g, 62%).

Step 4: Preparation of 3-(5-bromo-1H-indol-3-yl)propan-1-amine

The compound (0.1 g, 0.358 mmol) obtained in step 3 above was dissolved in tetrahydrofuran (3 ml) and water (0.2 ml), triphenylphosphine (0.47 g, 1.791 mmol) was added, then stirred at room temperature within 16 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and then purified by HPLC to give the title compound (0.075 g, 83%).

Step 5: Preparation of N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-bromopropoxy)benzenesulfonamide

The compound (0.094 g, 0.299 mmol) obtained in step 1 of Example 31 was dissolved in dichloromethane (1 ml), the compound (0.075 g, 0.299 mmol) obtained in step 4 above and potassium carbonate (0.124 g, 0.896 mmol) were added. , then stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and then purified by HPLC to give the title compound (0.12 g, 80%).

Step 6: Preparation of N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide

The compound (0.06 g, 0.113 mmol) obtained in step 5 above was dissolved in ethanol (1.5 ml), potassium carbonate (0.031 g, 0.226 mmol) and piperazine (0.02 g, 0.339 mmol) were added, then stirred at 70°C for 16 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, diluted with dichloromethane, and washed with water and brine. The remainder of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, purified using rep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.032 g, 53%, yellow solid).

The compounds of examples 154-156 were prepared similarly to the method described in example 153.

The compound of Example 147 was prepared similarly to the method described in Example 147.

The compounds of examples 158 and 159 were prepared similarly to the method described in example 31.

The compounds of Examples 160 and 161 were prepared similarly to the method described in Example 148.

The compounds of examples 162 and 163 were prepared similarly to the method described in example 31.

The compounds of Examples 164 and 165 were prepared similarly to the method described in Example 153.

The compound of Example 148 was prepared similarly to the method described in Example 148.

<Example 167> Preparation of N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

Step 1: Preparation of (cyanomethyl)triphenylphosphonium

2-Bromoacetonitrile (1.328 ml, 19.06 mmol) was dissolved in dichloromethane (80 ml), triphenylphosphine (5 g, 19.06 mmol) was added at room temperature, then stirred for 6 hours. After completion of the reaction, the mixture was washed with diethyl ether without further purification to give the title compound (7 g, 96%, white solid).

Step 2: Preparation of (E)-3-(5-chloro-1H-indazol-3-yl)acrylonitrile

(Cyanomethyl)triphenylphosphonium (3.17 g, 8.31 mmol) obtained in step 1 above was dissolved in anhydrous tetrahydrofuran (10 ml), sodium tert-butoxide (0.8 g, 8. 31 mmol), then stirred for 30 minutes. At -78°C, 5-chloro-1H-indazole-3-carbaldehyde (1.0 g, 5.44 mmol) dissolved in anhydrous tetrahydrofuran was added. The temperature of the reaction mixture was slowly raised to room temperature, then stirred for 1 hour. After completion of the reaction, the mixture was washed with a supersaturated aqueous ammonium chloride solution and extracted with ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, filtered and then separated and purified by HPLC to give the title compound (0.3 g, 27%, pale yellow solid).

Step 3: Preparation of 3-(5-chloro-1H-indazol-3-yl)propan-1-amine

(E)-3-(5-chloro-1H-indazol-3-yl)acrylonitrile (300 mg, 1.473 mmol) obtained in step 2 above was dissolved in ether (5 ml), LAH was added at -78°C (168 mg, 4.42 mmol). The temperature of the reaction mixture was slowly raised to room temperature, then stirred for 2 hours. The reaction was completed by adding additional LAH (112 mg, 2.95 mmol). After completion of the reaction, the mixture was filtered through celite. The filtrate was concentrated under reduced pressure and then separated and purified by HPLC to give the title compound (200 mg, 65%, yellow oil).

Step 4: Preparation of 4-(-bromopropoxy)-N-(3-(5-chloro-1H-indazol-3-yl)propyl)benzenesulfonamide

The title compound (75 mg, 18%, white solid) was prepared analogously to the method described in step 2 of example 31.

Step 5: Preparation of N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The title compound (13.3 mg, 85%, pale yellow solid) was prepared similarly to the method described in Example 148.

The compounds of examples 168-170 were prepared similarly to the method described in example 167.

<Example 171> Preparation of (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy) benzenesulfonamide

Step 1: Preparation of (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(oxiran-2-ylmethoxy)benzenesulfonamide

The compound (0.41 g, 1.026 mmol) obtained in step 1 of Example 92 was dissolved in dimethylformamide (3.4 ml), (R)-2-(chloromethyl)oxirane (0.095 g, 1.026 mmol) and potassium carbonate ( 0.21 g, 1.539 mmol), then stirred at 60°C for 16 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine. The residue of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and then purified by HPLC to give the title compound (0.16 g, 37%).

Step 2: Preparation of (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The compound (0.083 g, 0.198 mmol) obtained in step 1 above was dissolved in acetone (1 ml), 1-methylpiperazine (0.19 g, 1.981 mmol) and potassium carbonate (0.274 g, 1.981 mmol) were added, then stirred at temperature 80°C for 16 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine. The remainder of the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, purified using rep. HPLC and neutralized by adding aqueous sodium hydrogen carbonate to give the title compound (0.030 g, 30%, yellow solid).

The compounds of examples 172-174 were prepared similarly to the method described in example 171.

The compounds of Examples 175 and 176 were prepared similarly to the method described in Example 148.

<Example 177> Preparation of N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl) 4-(3-(4-methylpiperazin-1-yl)propoxy)- benzenesulfonamide

Step 1: Preparation of 4-(3-bromopropoxy)-N-(3-(5-chloro-1H-indazol-3-yl)propyl)benzenesulfonamide

The target compound was prepared analogously to the method described in step 2 of Example 31 using (6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methanamine prepared analogously to the method described in the reference literature [WO2006/ 89053].

Step 2: Preparation of N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide

The title compound (6.3 mg, 20%, pale yellow solid) was prepared analogously to the method described in Example 148.

The compound of Example 178 was prepared similarly to the method described in Example 177.

The compounds of Examples 179 and 180 were prepared similarly to the method described in Example 85.

<Example 181> Preparation of N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy )benzenesulfonamide

Step 1: Preparation of N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-methylbenzenesulfonamide

5-Chloro-1H-indole (0.400 g, 5.28 mmol) and N-(2-(2-hydroxypropan-2-yl)phenyl)-4-methylbenzenesulfonamide (0.967 g, 3.17 mmol) were dissolved in 1. 2-dichloroethane (40 ml), PdCl ₂ ·(CH ₃ CN) ₂ (0.0340 g, 0.132 mmol) was added, then stirred for 3 hours under nitrogen. After completion of the reaction, the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure and separated and purified by HPLC to give the title compound (1.02 g, 88%, white solid).

Step 2: Preparation of 2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)aniline

N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-methylbenzenesulfonamide (0.540 g, 1.23 mmol) obtained in step 1 above was dissolved in sulfuric acid (6 ml), then stirred at room temperature for 40 minutes. After completion of the reaction by adding ice, 2N aqueous sodium hydroxide solution was added dropwise to the reaction product to neutralize it. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then separated and purified by HPLC to give the title compound (0.175 g, 50%, pale yellow solid).

Step 3: Preparation of 4-(3-bromopropoxy)-N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)benzenesulfonamide

The target compound was prepared analogously to the method described in step 2 of example 31.

Step 4: Preparation of N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy) benzenesulfonamide

The title compound (17.2 mg, 33%, pale yellow solid) was prepared similarly to the method described in Example 148.

Example 182 was prepared similarly to the method described in Example 181.

The compounds of Examples 183 and 184 were prepared similarly to the method described in Example 153.

<Example 185> Preparation of N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyridin-4-yloxy)propyl)benzenesulfonamide

The title compound (18.5 mg, 60%, white solid) was prepared analogously to the method described in Example 148 using 4-(3-bromopropyl)-N-(3-(5-chloro-1H-indole-3 -yl)propyl)benzenesulfonamide prepared analogously to the method described in steps 1 and 2 of Example 90.

Example 186 was prepared similarly to the method described in Example 185.

The compounds of examples 187-190 were prepared similarly to the method described in example 177.

The compound names, structural formulas, and ¹ H NMR and MS analysis results of the compounds for Examples 1-190 are summarized in Table 1 below.

[Table 1] Etc. Structure Name ^1H NMR, MS 1 N-(3-([1,1'-biphenyl]-4-yl)propyl)-4-butoxybenzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.78-7.74 (m, 2H), 7.59-7.54 (m, 2H), 7.50-7.46 (m, 2H), 7.46-7.39 (m, 2H), 7.36-7.30 (m, 1H), 7.16 (d, J=8.2 Hz, 2H), 6.98-6.92 ( m, 2H), 4.24 (t, J=6.3 Hz, 1H), 4.00 (t, J=6.5 Hz, 2H), 2.99 (dd, J=13.4, 6 ,8 Hz, 2H), 2.69-2.62 (m, 2H), 1.80 (ddt, J=14.4, 12.7, 6.8 Hz, 4H), 1.47 (dd, J=14.8, 7.5 Hz, 2H), 0.98 (t, J=7.4 Hz, 3H); 424 [M+H] ⁺ 2 4-butoxy-N-(3-(4-isopropylpiperazin-1-yl)propyl)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.77 (d, J=8.9 Hz, 2H), 6.95 (d, J=8.9 Hz, 2H), 4.02 (t, J =6.5 Hz, 2H), 3.04 (t, J=5.6 Hz, 2H), 2.65-2.40 (m, 9H), 2.39 (t, J=5.8 Hz , 2H), 1.81-1.77 (m, 2H), 1.63-1.61 (m, 2H), 1.51-1.48 (m, 2H), 1.06 (d, J =6.5 Hz, 6H), 0.99 (t, J=7.4 Hz, 3H); 398.3 [M+H] ⁺ 3 4-butoxy-N-(3-(4-chlorophenyl)propyl)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.75 (d, J=8.9 Hz, 2H), 7.21 (d, J=8.4 Hz, 2H), 7.01 (d, J =8.4 Hz, 2H), 6.95 (d, J=8.9 Hz, 2H), 4.02 (t, J=6.5 Hz, 2H), 2.93 (t, J=6 .8 Hz, 2H), 2.58 (t, J=7.4 Hz, 2H), 1.82-1.74 (m, 4H), 1.53-1.48 (m, 2H), 0 .99 (t, J=7.4 Hz, 3H); 382.2 [M+H] ⁺ 4 4-butoxy-N-(3-cyclohexylpropyl)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.77 (d, J=9.0 Hz, 2H), 6.96 (d, J=9.0 Hz, 2H), 4.18 (t, J =6.2 Hz, 1H, NH), 4.02 (t, J=6.5 Hz, 2H), 2.93-2.88 (m, 2H), 1.79-1.77 (m, 2H), 1.64-1.46 (m, 11H), 1.13-1.10 (m, 6H), 0.99 (t, J=7.4 Hz, 3H); 354.3 [M+H] ⁺ 5 4-butoxy-N-(3-(pyridin-3-yl)propyl)benzene-sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.44 (d, J=3.7 Hz, 1H), 8.38 (s, 1H), 7.76 (d, J=8.8 Hz, 2H ), 7.44 (d, J=7.8 Hz, 1H), 7.20 (dd, J=7.6, 4.8 Hz, 1H), 6.96 (d, J=8.8 Hz , 2H), 4.41 (t, J=6.2 Hz, 1H, NH), 4.02 (t, J=6.5 Hz, 2H), 2.96 (dd, J=13.4, 6.8 Hz, 2H), 2.63 (t, J=7.5 Hz, 2H), 1.82-1.77 (m, 4H), 1.53-1.47 (m, 2H), 0.98 (t, J=7.4 Hz, 3H); 349 [M+H] ⁺ 6 4-butoxy-N-(3-morpholinopropyl)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.76 (d, J=8.9 Hz, 2H), 6.95 (d, J=8.9 Hz, 2H), 4.01 (t, J =6.5 Hz, 2H), 3.71 (t, J=4.6 Hz, 4H), 3.06 (t, J=5.8 Hz, 2H), 2.41 (t, J=5 .7 Hz, 4H), 1.81-1.77 (m, 2H), 1.66-1.61 (m, 2H), 1.56-1.47 (m, 4H), 0.99 ( t, J=7.4 Hz, 3H); 357 [M+H] ⁺ 7 4-butoxy-N-(4-morpholinophenethyl)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.74-7.69 (m, 2H), 7.02-6.96 (m, 2H), 6.96-6.91 (m, 2H), 6.84-6.80 (m, 2H), 4.24-4.14 (m, 1H), 4.01 (t, J=6.5 Hz, 2H), 3.92-3.80 ( m, 4H), 3.16 (dd, J=13.4, 6.9 Hz, 2H), 3.14-3.09 (m, 4H), 2.68 (t, J=6.8 Hz , 2H), 1.84-1.74 (m, 2H), 1.48 (dd, J=15.0, 7.5 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); 419.16 [M+H] ⁺ 8 4-(2-(4-butoxyphenylsulfonamido)ethyl)-benzoic acid ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.95 (d, J=7.9 Hz, 2H), 7.73 (d, J=8.6 Hz, 2H), 7.20 (d, J =7.5 Hz, 2H), 6.94 (d, J=8.8 Hz, 2H), 4.61 (s, 1H), 4.01 (t, J=6.5 Hz, 2H), 3.25 (dd, J=12.4, 5.9 Hz, 2H), 2.86 (t, J=6.4 Hz, 2H), 1.78 (dd, J=14.5, 6, 7 Hz, 2H), 1.50 (dt, J=22.4, 7.6 Hz, 2H), 0.98 (t, J=7.3 Hz, 3H); 378 [M+H] ⁺ 9 Methyl 4-(2-(4-butoxyphenylsulfone-amido)ethyl)benzoate ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.94 (d, J=8.2 Hz, 2H), 7.77-7.66 (m, 2H), 7.16 (d, J=8, 2 Hz, 2H), 6.97-6.88 (m, 2H), 4.22 (t, J=6.3 Hz, 1H), 4.01 (t, J=6.5 Hz, 2H) , 3.91 (s, 3H), 3.24 (dd, J=13.4, 6.8 Hz, 2H), 2.83 (t, J=6.9 Hz, 2H), 1.84- 1.75 (m, 2H), 1.48 (dd, J=14.8, 7.4 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); 392 [M+H] ⁺ 10 N-(2-(4-benzylpiperidin-1-yl)ethyl)-4-butoxy-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.77 (d, J=8.9 Hz, 2H), 7.28 (d, J=7.1 Hz, 2H), 7.19 (t, J =7.3 Hz, 1H), 7.12 (d, J=7.0 Hz, 2H), 6.95 (d, J=8.9 Hz, 2H), 5.20 (s, 1H), 4.00 (t, J=6.5 Hz, 2H), 2.94 (d, J=5.6 Hz, 2H), 2.53 (dd, J=16.1, 9.2 Hz, 4H ), 2.33 (t, J=5.7 Hz, 2H), 1.88-1.74 (m, 4H), 1.57-1.44 (m, 5H), 1.21-1, 08 (m, 2H), 0.98 (t, J=7.4 Hz, 3H); 431 [M+H] ⁺ eleven 4-butoxy-N-(3-hydroxy-3-phenylpropyl)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.83-7.75 (m, 2H), 7.32 (dt, J=12.9, 4.4 Hz, 2H), 7.28-7, 23 (m, 3H), 7.00-6.91 (m, 2H), 5.05-4.99 (m, 2H), 4.81 (td, J=6.3, 3.2 Hz, 2H), 4.02 (t, J=6.5 Hz, 2H), 3.27-2.98 (m, 2H), 1.86 (dt, J=9.5, 4.7 Hz, 2H ), 1.83-1.73 (m, 2H), 1.54-1.46 (m, 3H), 0.99 (t, J=7.4 Hz, 3H); 364 [M+H] ⁺ 12 4-butoxy-N-(3-oxo-3-phenylpropyl)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.88 (d, J=7.2 Hz, 2H), 7.80 (d, J=8.9 Hz, 2H), 7.59 (t, J =7.4 Hz, 1H), 7.46 (t, J=7.7 Hz, 2H), 6.95 (d, J=8.9 Hz, 2H), 5.15 (t, J=6 .8 Hz, 1H), 4.00 (t, J=6.5 Hz, 2H), 3.34 (dd, J=11.9, 5.8 Hz, 2H), 3.25-3.16 (m, 2H), 1.85-1.72 (m, 2H), 1.53-1.45 (m, 2H), 0.99 (t, J=7.4 Hz, 3H); 362 [M+H] ⁺ 13 4-butoxy-N-(3-(2-oxopyrrolidin-1-yl)propyl)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.81-7.72 (m, 2H), 6.97-6.89 (m, 2H), 5.75 (t, J=6.8 Hz, 1H), 4.01 (t, J=6.5 Hz, 2H), 3.33 (dd, J=9.1, 5.1 Hz, 4H), 2.86 (dd, J=12.4 , 6.6 Hz, 2H), 2.34 (t, J=8.1 Hz, 2H), 2.05-1.95 (m, 2H), 1.83-1.75 (m, 2H) , 1.69 (dt, J=12.2, 6.2 Hz, 2H), 1.49 (dt, J=14.7, 7.5 Hz, 2H), 0.98 (t, J=7 ,4 Hz, 3H); 355 [M+H] ⁺ 14 4-(3-(dimethylamino)-propoxy)-N-phenethyl-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.76-7.67 (m, 2H), 7.31-7.19 (m, 3H), 7.10-7.01 (m, 2H), 6.99-6.90 (m, 2H), 4.27 (t, J=6.3 Hz, 1H), 4.08 (t, J=6.4 Hz, 2H), 3.21 (kv , J=6.8 Hz, 2H), 2.76 (t, J=6.9 Hz, 2H), 2.48 (t, J=7.1 Hz, 2H), 2.28 (s, 6H ), 2.05-1.92 (m, 2H); 363 [M+H] ⁺ 15 4-(3-(dimethylamino)-propoxy)-N-(3-phenylpropyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.78-7.73 (m, 2H), 7.29-7.21 (m, 2H), 7.21-7.15 (m, 1H), 7.11-7.05 (m, 2H), 6.99-6.93 (m, 2H), 4.31 (t, J=6.2 Hz, 1H), 4.08 (t, J= 6.4 Hz, 2H), 2.96 (dd, J=13.4, 6.8 Hz, 2H), 2.65-2.57 (m, 2H), 2.49 (t, J=7 ,1 Hz, 2H), 2.28 (s, 6H), 2.04-1.95 (m, 2H), 1.79 (dt, J=14.2, 7.0 Hz, 2H); 377 [M+H] ⁺ 16 Methyl 4-(2-(4-(3-(dimethylamino)propoxy)-phenylsulfone-amido)ethyl)benzoate ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.96-7.92 (m, 2H), 7.75-7.67 (m, 2H), 7.16 (d, J=8.3 Hz, 2H), 6.99-6.89 (m, 2H), 4.27 (t, J=6.2 Hz, 1H), 4.08 (t, J=6.4 Hz, 2H), 3, 91 (s, 3H), 3.23 (kv, J=6.8 Hz, 2H), 2.83 (t, J=6.9 Hz, 2H), 2.48 (t, J=7.1 Hz, 2H), 2.28 (s, 6H), 2.03-1.94 (m, 2H); 421 [M+H] ⁺ 17 4-(2-(4-(3-(dimethylamino)propoxy)-phenylsulfone-amido)ethyl)benzoic acid ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.56 (d, J=8.1 Hz, 2H), 7.21 (d, J=8.9 Hz, 2H), 6.87 (d, J =8.1 Hz, 2H), 6.58 (d, J=8.9 Hz, 2H), 4.28 (dd, J=12.3, 4.9 Hz, 1H), 4.11-4 .00 (m, 2H), 3.56-3.49 (m, 2H), 3.06-2.97 (m, 2H), 2.68 (s, 2H), 2.66 (s, 6H ), 2.13-2.07 (m, 2H); 407 [M+H] ⁺ 18 4-(3-(dimethylamino)-propoxy)-N-(3-(2-oxopyrrolidin-1-yl)propyl)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.82-7.73 (m, 2H), 6.98-6.93 (m, 2 H), 5.77 (t, J=6.8 Hz , 1H), 4.07 (t, J=6.4 Hz, 2H), 3.33 (dd, J=9.4, 4.9 Hz, 4H), 2.85 (dd, J=12, 4, 6.6 Hz, 2H), 2.45 (t, J=7.1 Hz, 2H), 2.35 (d, J=7.9 Hz, 2H), 2.25 (s, 6H) , 2.05-1.91 (m, 4H), 1.69 (dt, J=12.3, 6.1 Hz, 2H); 384 [M+H] ⁺ 19 4-butoxy-N-(3-(naphthalene-1-yl)propyl)benzene-sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.92-7.83 (m, 2H), 7.74 (d, J=38.9 Hz, 2H), 7.71 (d, J=8, 5 Hz, 1H), 7.50-7.46 (m, 2H), 7.35 (dd, J=8.1, 7.0 Hz, 1H), 7.22 (d, J=6.8 Hz, 1H), 6.93 (d, J=8.9 Hz, 2H), 4.27 (t, J=6.1 Hz, 1H, NH), 4.01 (t, J=6.5 Hz, 2H), 3.09-3.02 (m, 4H), 1.95-1.88 (m, 2H), 1.83-1.76 (m, 2H), 1.52-1. 48 (m, 2H), 0.99 (t, J=7.4 Hz, 3H); 398 [M+H] ⁺ 20 N-(3-(1H-indol-3-yl)propyl)-4-butoxy-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.92 (s, 1H), 7.75-7.69 (m, 2H), 7.49 (d, J=7.9 Hz, 1H), 7 .35 (d, J=8.1 Hz, 1H), 7.22-7.15 (m, 1H), 7.12-7.05 (m, 1H), 6.95-6.90 (m , 3H), 4.25-4.18 (m, 1H), 4.00 (t, J=6.5 Hz, 2H), 3.01 (dd, J=13.3, 6.8 Hz, 2H), 2.77 (t, J=7.2 Hz, 2H), 1.91-1.83 (m, 2H), 1.83-1.72 (m, 2H), 1.48 (dd , J=14.8, 7.5 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); 387.01 [M+H] ⁺ 21 N-(3-(1H-indol-3-yl)propyl)-4-(2-(dimethylamino)ethoxy)benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.08 (s, 1H), 7.75-7.69 (m, 2H), 7.49 (d, J=7.9 Hz, 1H), 7 .35 (d, J=8.1 Hz, 1H), 7.22-7.15 (m, 1H), 7.12-7.05 (m, 1H), 6.95-6.90 (m , 3H), 4.25-4.18 (m, 1H), 4.00 (t, J=6.5 Hz, 2H), 3.01 (dd, J=13.3, 6.8 Hz, 2H), 2.77 (t, J=7.2 Hz, 2H), 1.91-1.83 (m, 2H), 1.83-1.72 (m, 2H), 1.48 (dd , J=14.8, 7.5 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); 387.01 [M+H] ⁺ 22 N-(3-(1H-indol-3-yl)propyl)-4-(3-(dimethylamino)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.37 (s, 1H), 7.74-7.69 (m, 2H), 7.49 (d, J=7.6 Hz, 1H), 7 .34 (d, J=8.1 Hz, 1H), 7.21-7.16 (m, 1H), 7.11-7.06 (m, 1H), 6.95-6.90 (m , 2H), 6.80 (d, J=2.3 Hz, 1H), 4.25-4.18 (m, 1H), 4.09 (t, J=6.3 Hz, 2H), 2 .99 (dd, J=13.1, 6.7 Hz, 2H), 2.74 (t, J=7.1 Hz, 2H), 2.48 (t, J=7.0 Hz, 2H) , 2.28 (s, 6H), 1.99 (dt, J=13.4, 6.7 Hz, 2H), 1.85 (dt, J=14.1, 7.0 Hz, 2H); 416 [M+H] ⁺ 23 N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)-4-butoxy-benzenesulfonamide ^1H NMR (400 MHz, MeOD) δ 7.74-7.68 (m, 2H), 7.48 (s, 2H), 7.24-7.18 (m, 2H), 6.97-6 .90 (m, 2H), 4.03 (t, J=6.4 Hz, 2H), 3.38-3.34 (m, 2H), 3.05 (d, J=7.1 Hz, 2H), 1.78 (dd, J=14.8, 6.7 Hz, 2H), 1.54 (dkv, J=14.8, 7.4 Hz, 2H), 1.02 (t, J =7.4 Hz, 3H) ; 374 [M+H] ⁺ 24 N-(2-(1H-indol-3-yl)-ethyl)-4-butoxy-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.00 (s, 1H), 7.69-7.64 (m, 2H), 7.42 (d, J=7.9 Hz, 1H), 7 .36 (d, J=8.2 Hz, 1H), 7.19 (t, J=7.2 Hz, 1H), 7.07 (t, J=7.5 Hz, 1H), 6.99 (d, J=2.3 Hz, 1H), 6.90-6.84 (m, 2H), 4.28 (t, J=6.1 Hz, 1H), 3.99 (t, J= 6.5 Hz, 2H), 3.28 (kv, J=6.5 Hz, 2H), 2.94 (t, J=6.6 Hz, 2H), 1.84-1.73 (m, 2H), 1.48 (dd, J=14.8, 7.4 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); 373 [M+H] ⁺ 25 N-(2-(1H-indol-2-yl)-ethyl)-4-butoxy-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.00 (s, 1H), 7.75-7.67 (m, 2H), 7.51 (d, J=7.7 Hz, 1H), 7 .29 (d, J=8.2 Hz, 1H), 7.14 (dd, J=11.0, 4.1 Hz, 1H), 7.09 (dd, J=10.9, 4.0 Hz, 1H), 6.96-6.88 (m, 2H), 6.21 (s, 1H), 4.43 (t, J=6.3 Hz, 1H), 4.01 (t, J =6.5 Hz, 2H), 3.28 (kv, J=6.4 Hz, 2H), 2.96 (t, J=6.4 Hz, 2H), 1.84-1.75 (m , 2H), 1.57-1.44 (m, 2H), 0.99 (t, J=7.4 Hz, 3H); 373 [M+H] ⁺ 26 N-(3-(1H-indol-3-yl)propyl)-4-(isopentyloxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.92 (s, 1H), 7.72 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.6 Hz, 1H ), 7.35 (d, J=8.2 Hz, 1H), 7.19 (t, J=7.1 Hz, 1H), 7.09 (t, J=7.2 Hz, 1H), 6.95 (d, J=2.1 Hz, 1H), 6.92 (d, J=8.9 Hz, 2H), 4.22 (t, J=6.2 Hz, 1H), 4, 03 (t, J=6.6 Hz, 2H), 3.01 (dd, J=13.3, 6.7 Hz, 2H), 2.77 (t, J=7.2 Hz, 2H), 1.91-1.79 (m, 3H), 1.70 (kv, J=6.7 Hz, 2H), 0.98 (s, 3H), 0.97 (s, 3H); 401 [M+H] ⁺ 27 N-(3-(1H-indol-3-yl)propyl)-4-(pentyloxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.92 (s, 1H), 7.72 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.6 Hz, 1H ), 7.35 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.09 (t, J=7.4 Hz, 1H), 6.95 (s, 1H), 6.92 (d, J=8.9 Hz, 2H), 4.21 (t, J=6.2 Hz, 1H), 3.99 (t, J=6 .5 Hz, 2H), 3.01 (dd, J=13.3, 6.8 Hz, 2H), 2.77 (t, J=7.1 Hz, 2H), 1.88 (dd, J =14.2, 7.1 Hz, 2H), 1.80 (dd, J=14.6, 6.7 Hz, 2H), 1.49-1.34 (m, 4H), 0.94 ( t, J=7.1 Hz, 3H) ; 401 [M+H] ⁺ 28 N-(3-(1H-benzo[d]-imidazol-2-yl)propyl)-4-butoxy-benzenesulfonamide ^1H NMR (400 MHz, MeOD) δ 7.75-7.66 (m, 2H), 7.50 (s, 2H), 7.27-7.17 (m, 2H), 7.00 (d , J=8.9 Hz, 2H), 4.03 (t, J=6.4 Hz, 2H), 2.92 (t, J=7.0 Hz, 4H), 2.06-1.96 (m, 2H), 1.83-1.69 (m, 2H), 1.52 (dt, J=14.7, 7.5 Hz, 2H), 1.01 (t, J=7.4 Hz, 3H); 388 [M+H] ⁺ 29 4-butoxy-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.88 (s, 1H), 7.70-7.63 (m, 2H), 7.23-7.18 (m, 1H), 6.97 ( d, J=2.4 Hz, 1H), 6.91-6.86 (m, 1H), 6.80-6.71 (m, 2H), 4.45 (s, 1H), 4.27 (t, J=6.3 Hz, 1H), 4.00 (t, J=6.5 Hz, 2H), 3.24 (dd, J=12.9, 6.5 Hz, 2H), 2 .87 (t, J=6.6 Hz, 2H), 1.80 (dd, J=14.4, 7.2 Hz, 2H), 1.48 (dd, J=14.8, 7.5 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); 389 [M+H] ⁺ thirty N-(3-(1H-indol-3-yl)propyl)-4-(3-morpholinopropoxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.02 (s, 1H), 7.75-7.69 (m, 2H), 7.49 (d, J=7.1 Hz, 1H), 7 .35 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.0 Hz, 1H), 7.12-7.06 (m, 1H), 6.96-6, 88 (m, 3H), 4.23 (t, J=6.3 Hz, 1H), 4.08 (t, J=6.3 Hz, 2H), 3.79-3.66 (m, 4H ), 3.01 (dd, J=13.3, 6.8 Hz, 2H), 2.77 (t, J=7.1 Hz, 2H), 2.58-2.50 (m, 2H) , 2.48-2.46 (m, 4H), 2.00 (dd, J=13.6, 6.6 Hz, 2H), 1.87 (dt, J=14.2, 7.0 Hz , 2H); 458 [M+H] ⁺ 31 N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.10 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.9 Hz, 1H ), 7.35 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.2 Hz, 1H), 7.09 (t, J=7.4 Hz, 1H), 6.92 (d, J=8.8 Hz, 3H), 4.24 (t, J=6.3 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3, 01 (dd, J=13.3, 6.7 Hz, 2H), 2.76 (t, J=7.3 Hz, 2H), 2.69-2.36 (m, 10H), 2.31 (s, 3H), 2.05-1.93 (m, 2H), 1.90-1.80 (m, 2H); 471 [M+H] ⁺ 32 N-(3-(1H-indol-1-yl)propyl)-4-butoxybenzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.72-7.64 (m, 2H), 7.62 (d, J=7.9 Hz, 1H), 7.28-7.26 (m, 1H), 7.23-7.15 (m, 1H), 7.13-7.07 (m, 1H), 7.05 (d, J=3.1 Hz, 1H), 6.95-6 .86 (m, 2H), 6.53-6.47 (m, 1H), 4.24-4.13 (m, 3H), 4.00 (t, J=6.5 Hz, 2H), 2.88 (dd, J=12.9, 6.4 Hz, 2H), 2.10-1.95 (m, 2H), 1.84-1.74 (m, 2H), 1.54- 1.40 (m, 2H), 0.99 (t, J=7.4 Hz, 3H); 387 [M+H] ⁺ 33 N-(3-(1H-benzo[d]-imidazol-1-yl)propyl)-4-butoxy-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.92 (s, 1H), 7.83-7.78 (m, 1H), 7.75-7.71 (m, 2H), 7.39- 7.34 (m, 1H), 7.29 (dt, J=5.3, 3.5 Hz, 2H), 6.96-6.90 (m, 2H), 4.44 (dd, J= 8.1, 7.2 Hz, 1H), 4.31 (t, J=6.7 Hz, 2H), 4.00 (t, J=6.5 Hz, 2H), 2.91 (dd, J=12.8, 6.4 Hz, 2H), 2.13-2.04 (m, 2H), 1.79 (dt, J=14.3, 6.4 Hz, 2H), 1.49 (dt, J=14.7, 7.5 Hz, 2H), 0.98 (t, J=7.4 Hz, 3H); 388 [M+H] ⁺ 34 N-(3-(1H-benzo[d]imidazol-1-yl)propyl)-4-butoxy-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.05 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.49 (d, J=8.5 Hz, 1H ), 7.35 (d, J=8.2 Hz, 1H), 7.21-7.15 (m, 1H), 7.12-7.07 (m, 1H), 6.92 (d, J=8.9 Hz, 3H), 4.22 (d, J=6.4 Hz, 1H), 4.17-4.08 (m, 2H), 3.00 (dd, J=13.3 , 6.8 Hz, 2H), 2.83-2.72 (m, 4H), 2.53-2.50 (m, 4H), 1.86 (dt, J=14.4, 7.1 Hz, 2H), 1.61 (d, J=5.4 Hz, 4H), 1.45 (s, 2H);442 [M+H] ⁺ 35 N-(3-(1H-indol-3-yl)propyl)-4-(3-(diethylamino)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.22 (s, 1H), 7.76-7.68 (m, 2H), 7.49 (d, J=7.7 Hz, 1H), 7 .35 (d, J=8.1 Hz, 1H), 7.21-7.15 (m, 1H), 7.11-7.06 (m, 1H), 6.96-6.89 (m , 2H), 6.87 (d, J=2.2 Hz, 1H), 4.28 (t, J=6.2 Hz, 1H), 4.08 (t, J=6.2 Hz, 2H ), 3.00 (kv, J=6.7 Hz, 2H), 2.75 (t, J=7.2 Hz, 2H), 2.71-2.46 (m, 6H), 2.05 -1.94 (m, 2H), 1.89-1.80 (m, 2H), 1.08 (t, J=7.1 Hz, 6H); 444 [M+H] ⁺ 36 N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-ethylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.12 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.7 Hz, 1H ), 7.35 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.1 Hz, 1H), 7.09 (t, J=7.0 Hz, 1H), 6.92 (d, J=8.8 Hz, 3H), 4.24 (t, J=6.4 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3, 00 (dd, J=13.3, 6.7 Hz, 2H), 2.76 (t, J=7.2 Hz, 2H), 2.53-2.44 (m, 12H), 2.00 (dt, J=13.3, 6.5 Hz, 2H), 1.90-1.78 (m, 2H), 1.11 (t, J=7.0 Hz, 3H); 485 [M+H] ⁺ 37 N-(2-(1H-benzo[d]-imidazol-2-yl)-ethyl)-4-(3-(dimethylamino)-propoxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.77 (d, J=8.9 Hz, 2H), 7.26-7.22 (m, 4H), 6.93 (d, J=8, 9 Hz, 2H), 5.73-5.67 (m, 1H), 4.08 (t, J=6.4 Hz, 2H), 3.47 (dd, J=11.9, 6.0 Hz, 2H), 3.07-3.01 (m, 2H), 2.50-2.44 (m, 2H), 2.27 (s, 6H), 1.99 (dd, J=13, 7, 6.7 Hz, 2H);403 [M+H] ⁺ 38 N-(2-(1H-indol-2-yl)ethyl)-4-(3-(dimethylamino)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.06 (s, 1H), 7.75-7.68 (m, 2H), 7.51 (d, J=7.7 Hz, 1H), 7 .29 (d, J=8.1 Hz, 1H), 7.17-7.11 (m, 1H), 7.11-7.05 (m, 1H), 6.97-6.90 (m , 2H), 6.20 (d, J=1.2 Hz, 1H), 4.48 (s, 1H), 4.07 (t, J=6.4 Hz, 2H), 3.27 (dd , J=12.6, 6.3 Hz, 2H), 2.95 (t, J=6.4 Hz, 2H), 2.47 (t, J=7.1 Hz, 2H), 2.27 (s, 6H), 2.05-1.94 (m, 2H); 402 [M+H] ⁺ 39 N-(3-(1H-indol-1-yl)propyl)-4-(3-(dimethylamino)propoxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.70-7.64 (m, 2H), 7.62 (d, J=7.9 Hz, 1H), 7.28-7.26 (m, 1H), 7.21-7.15 (m, 1H), 7.13-7.06 (m, 1H), 7.05 (d, J=3.2 Hz, 1H), 6.96-6 .88 (m, 2H), 6.50-6.45 (m, 1H), 4.27-4.15 (m, 3H), 4.06 (t, J=6.4 Hz, 2H), 2.88 (dd, J=13.0, 6.5 Hz, 2H), 2.46 (t, J=6.9 Hz, 2H), 2.26 (s, 6H), 2.00 (td , J=13.4, 6.8 Hz, 4H); 416 [M+H] ⁺ 40 N-(3-(1H-benzo[d]-imidazol-1-yl)propyl)-4-(3-(dimethylamino)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.92 (s, 1H), 7.84-7.79 (m, 1H), 7.76-7.71 (m, 2H), 7.39- 7.34 (m, 1H), 7.30 (dt, J=5.4, 3.5 Hz, 2H), 6.97-6.92 (m, 2H), 4.55 (d, J= 6.1 Hz, 1H), 4.31 (t, J=6.7 Hz, 2H), 4.07 (t, J=6.4 Hz, 2H), 2.90 (dd, J=12, 7, 6.4 Hz, 2H), 2.46 (t, J=7.0 Hz, 2H), 2.27 (s, 6H), 2.13-2.03 (m, 2H), 1, 98 (dt, J=13.5, 6.7 Hz, 2H); 417 [M+H] ⁺ 41 N-(3-(1H-indol-1-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.71-7.65 (m, 2H), 7.62 (d, J=7.9 Hz, 1H), 7.30-7.27 (m, 1H), 7.19 (dd, J=8.1, 7.1 Hz, 1H), 7.11 (dd, J=10.9, 4.0 Hz, 1H), 7.05 (d, J =3.1 Hz, 1H), 6.94-6.89 (m, 2H), 6.48 (d, J=3.1 Hz, 1H), 4.20 (t, J=6.6 Hz , 2H), 4.16 (t, J=6.5 Hz, 1H), 4.06 (t, J=6.3 Hz, 2H), 2.88 (dd, J=12.9, 6, 5 Hz, 2H), 2.69-2.35 (m, 10H), 2.29 (s, 3H), 2.00 (tt, J=9.9, 6.5 Hz, 4H); 471 [M+H] ⁺ 42 N-(3-(1H-benzo[d]imidazol-1-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.92 (s, 1H), 7.83-7.78 (m, 1H), 7.73 (d, J=8.9 Hz, 2H), 7 .38-7.34 (m, 1H), 7.32-7.28 (m, 2H), 6.95 (d, J=8.9 Hz, 2H), 4.36-4.28 (m , 3H), 4.06 (t, J=6.3 Hz, 2H), 2.91 (dd, J=12.8, 6.4 Hz, 2H), 2.59-2.35 (m, 10H), 2.29 (s, 3H), 2.07 (dd, J=13.1, 6.6 Hz, 2H), 2.02-1.94 (m, 2H); 472 [M+H] ⁺ 43 N-(3-(1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.73-7.66 (m, 2H), 7.49 (d, J=7.7 Hz, 1H), 7, 35 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.0 Hz, 1H), 7.09 (t, J=7.0 Hz, 1H), 6.94- 6.89 (m, 2H), 6.88 (t, J=2.6 Hz, 1H), 4.23 (t, J=6.1 Hz, 1H), 4.08 (t, J=6 .3 Hz, 2H), 3.00 (dd, J=13.3, 6.7 Hz, 2H), 2.75 (t, J=7.1 Hz, 2H), 2.62-2.32 (m, 6H), 2.07-1.94 (m, 2H), 1.90-1.79 (m, 2H), 1.69-1.60 (m, 4H), 1.47 (dd , J=16.1, 10.0 Hz, 2H); 456 [M+H] ⁺ 44 N-(3-(1H-indol-3-yl)propyl)-4-(3-(2-oxopyrrolidin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.70 (s, 1H), 7.74-7.67 (m, 2H), 7.49 (d, J=7.5 Hz, 1H), 7 .35 (d, J=8.2 Hz, 1H), 7.19-7.13 (m, 1H), 7.11-7.05 (m, 1H), 6.91 (d, J=7 ,1 Hz, 2H), 6.64 (s, 1H), 4.25-4.18 (m, 1H), 4.04 (t, J=5.1 Hz, 2H), 3.54 (t , J=6.4 Hz, 2H), 3.46 (t, J=6.9 Hz, 2H), 2.98 (dd, J=12.2, 5.8 Hz, 2H), 2.74 (t, J=6.9 Hz, 2H), 2.40 (t, J=8.0 Hz, 2H), 2.12-1.98 (m, 4H), 1.91-1.82 ( m, 2H); 456 [M+H] ⁺ 45 N-(3-(1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.13 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.7 Hz, 1H ), 7.35 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.1 Hz, 1H), 7.09 (t, J=7.1 Hz, 1H), 6.92 (d, J=8.9 Hz, 2H), 4.26 (t, J=6.4 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3, 00 (dd, J=13.2, 6.7 Hz, 2H), 2.90 (t, J=4.9 Hz, 4H), 2.76 (t, J=7.2 Hz, 2H), 2.55-2.48 (m, 2H), 2.45 (br, 4H), 2.07-1.93 (m, 2H), 1.91-1.79 (m, 2H); 457 [M+H] ⁺ 46 4-(3-(dimethylamino)-propoxy)-N-(3-(1-methyl-1H-indol-3-yl)propyl)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.75-7.69 (m, 2H), 7.47 (d, J=7.9 Hz, 1H), 7.28-7.26 (m, 1H), 7.21 (t, J=7.6 Hz, 1H), 7.08 (dd, J=10.9, 4.0 Hz, 1H), 6.97-6.90 (m, 2H ), 6.77 (s, 1H), 4.22 (t, J=6.2 Hz, 1H), 4.07 (t, J=6.4 Hz, 2H), 3.72 (s, 3H ), 3.00 (dd, J=13.3, 6.7 Hz, 2H), 2.75 (t, J=7.3 Hz, 2H), 2.46 (t, J=7.2 Hz , 2H), 2.26 (s, 6H), 1.98 (dt, J=13.4, 6.7 Hz, 2H), 1.89-1.81 (m, 2H); 430 [M+H] ⁺ 47 N-(3-(1H-indol-3-yl)propyl)-4-bromobenzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.95 (s, 1H), 7.66-7.56 (m, 4H), 7.48 (d, J=7.8 Hz, 1H), 7 .37 (d, J=8.1 Hz, 1H), 7.21 (t, J=7.6 Hz, 1H), 7.11 (t, J=7.1 Hz, 1H), 6.95 (d, J=2.2 Hz, 1H), 4.32 (t, J=5.9 Hz, 1H), 3.04 (dd, J=13.3, 6.7 Hz, 2H), 2 .78 (t, J=7.1 Hz, 2H), 1.88 (p, J=7.1 Hz, 2H); 394 [M+H] ⁺ 48 N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-isopropylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.10 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.8 Hz, 1H ), 7.35 (d, J=8.2 Hz, 1H), 7.20-7.16 (m, 1H), 7.11-7.06 (m, 1H), 6.94-6, 88 (m, 3H), 4.26-4.21 (m, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.01 (dd, J=13.4, 6, 8 Hz, 2H), 2.76 (t, J=7.4 Hz, 2H), 2.71-2.46 (m, 10H), 2.26-2.17 (m, 1H), 1, 99 (dd, J=12.5, 5.8 Hz, 2H), 1.87 (dd, J=14.2, 7.2 Hz, 2H), 1.06 (d, J=5.5 Hz , 6H); 499 [M+H] ⁺ 49 N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.96 (s, 1H), 7.64 (d, J=8.9 Hz, 2H), 7.29-7.21 (m, 1H), 6 .94 (d, J=2.1 Hz, 1H), 6.86 (dd, J=7.6, 5.4 Hz, 3H), 4.32-4.24 (m, 1H), 4, 05 (t, J=6.2 Hz, 2H), 3.80 (s, 3H), 3.26 (dd, J=12.8, 6.5 Hz, 2H), 2.91 (t, J =6.5 Hz, 2H), 2.73-2.34 (m, 10H), 2.29 (s, 3H), 2.04-1.93 (m, 2H); 487 [M+H] ⁺ 50 N-(2-(1H-indol-3-yl)-ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.10 (s, 1H), 7.65 (d, J=8.9 Hz, 2H), 7.43 (d, J=8.1 Hz, 1H ), 7.36 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.2 Hz, 1H), 7.07 (t, J=7.5 Hz, 1H), 6.97 (d, J=2.2 Hz, 1H), 6.88 (d, J=8.9 Hz, 2H), 4.29 (t, J=6.1 Hz, 1H), 4, 06 (t, J=6.3 Hz, 2H), 3.28 (dd, J=12.8, 6.4 Hz, 2H), 2.94 (t, J=6.6 Hz, 2H), 2.67-2.33 (m, 10H), 2.30 (s, 3H), 2.04-1.95 (m, 2H); 457 [M+H] ⁺ 51 N-(2-(1H-indol-3-yl)-ethyl)-4-(3-(4-isopropylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.10 (s, 1H), 7.65 (d, J=8.9 Hz, 2H), 7.43 (d, J=7.9 Hz, 1H ), 7.36 (d, J=8.2 Hz, 1H), 7.23-7.16 (m, 1H), 7.07 (t, J=7.6 Hz, 1H), 6.97 (s, 1H), 6.88 (d, J=8.9 Hz, 2H), 4.29 (t, J=6.2 Hz, 1H), 4.06 (t, J=6.3 Hz , 2H), 3.28 (dd, J=12.9, 6.5 Hz, 2H), 2.94 (t, J=6.5 Hz, 2H), 2.78-2.37 (m, 10H), 2.07-1.95 (m, 2H), 1.16-0.97 (m, 6H); 485 [M+H] ⁺ 52 N-(3-(1H-indol-3-yl)propyl)-4-(2-(4-methylpiperazin-1-yl)ethoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.31 (s, 1H), 7.73 (d, J=8.9 Hz, 2H), 7.49 (d, J=8.1 Hz, 1H ), 7.34 (d, J=8.1 Hz, 1H), 7.18 (t, J=7.1 Hz, 1H), 7.09 (t, J=7.0 Hz, 1H), 6.93 (d, J=8.9 Hz, 2H), 6.87 (d, J=2.3 Hz, 1H), 4.26 (t, J=6.2 Hz, 1H), 4, 15 (t, J=5.6 Hz, 2H), 3.02 (dd, J=13.3, 6.8 Hz, 2H), 2.88 (t, J=5.6 Hz, 2H), 2.74 (t, J=7.2 Hz, 2H), 2.69-2.39 (m, 8H), 2.32 (s, 2H), 1.83 (dd, J=14.2, 7.1 Hz, 2H); 457 [M+H] ⁺ 53 N-(3-(1H-indol-3-yl)propyl)-4-(2-(4-isopropylpiperazin-1-yl)ethoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.20 (s, 1H), 7.72 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.9 Hz, 1H ), 7.35 (d, J=8.0 Hz, 1H), 7.22-7.15 (m, 1H), 7.12-7.06 (m, 1H), 6.92 (d, J=8.9 Hz, 2H), 6.89 (d, J=2.2 Hz, 1H), 4.27-4.20 (m, 1H), 4.15 (t, J=5.7 Hz, 2H), 3.01 (dd, J=13.2, 6.6 Hz, 2H), 2.86 (t, J=5.7 Hz, 2H), 2.75 (t, J=7 ,3 Hz, 2H), 2.72-2.39 (m, 8H), 2.25-2.19 (m, 1H), 1.84 (dt, J=14.3, 7.2 Hz, 2H), 1.06 (d, J=5.9 Hz, 6H); 485 [M+H] ⁺ 54 N-(2-(2-methyl-1H-indol-3-yl)-ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.96 (s, 1H), 7.61 (d, J=8.9 Hz, 2H), 7.31 (d, J=7.9 Hz, 1H ), 7.25 (d, J=7.5 Hz, 1H), 7.11 (t, J=7.0 Hz, 1H), 7.02 (t, J=7.9 Hz, 1H), 6.85 (d, J=8.9 Hz, 2H), 4.24 (t, J=6.2 Hz, 1H), 4.06 (t, J=6.3 Hz, 2H), 3, 21 (kv, J=6.5 Hz, 2H), 2.89 (t, J=6.6 Hz, 2H), 2.73-2.37 (m, 10H), 2.34 (s, 3H ), 2.29 (s, 3H), 1.99 (dt, J=13.4, 6.5 Hz, 2H); 471 [M+H] ⁺ 55 N-(3-(1H-indol-3-yl)propyl)-4-(2-(1-methylpiperidin-4-yl)ethoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.22 (s, 1H), 7.72 (d, J=8.9 Hz, 2H), 7.49 (d, J=8.0 Hz, 1H ), 7.34 (d, J=8.1 Hz, 1H), 7.18 (t, J=7.2 Hz, 1H), 7.09 (t, J=7.5 Hz, 1H), 6.91 (d, J=8.8 Hz, 2H), 4.27 (t, J=6.2 Hz, 1H), 4.05 (t, J=6.4 Hz, 2H), 3, 02 (kv, J=6.7 Hz, 2H), 2.89 (d, J=11.7 Hz, 2H), 2.75 (t, J=7.3 Hz, 2H), 2.30 ( s, 3H), 1.97 (t, J=11.6 Hz, 2H), 1.85 (dd, J=14.3, 7.1 Hz, 2H), 1.76 (dt, J=13 ,4, 6.7 Hz, 4H), 1.45-1.34 (m, 2H); 456 [M+H] ⁺ 56 N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.10 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.28-7.23 (m, 2H), 7 ,10 (dd, J=9.6, 2.4 Hz, 1H), 6.99-6.88 (m, 4H), 4.25 (t, J=6.2 Hz, 1H), 4, 07 (t, J=6.3 Hz, 2H), 3.00 (dd, J=13.3, 6.8 Hz, 2H), 2.70 (t, J=7.3 Hz, 2H), 2.65-2.35 (m, 10H), 2.30 (s, 3H), 2.04-1.95 (m, 2H), 1.90-1.77 (m, 2H); 489 [M+H] ⁺ 57 3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)-sulfonyl)piperidin-4-yl)-1H-indole ^1H NMR (400 MHz, CDCl ₃ ) δ 8.03 (s, 1H), 7.74 (d, J=8.9 Hz, 2H), 7.51 (d, J=8.0 Hz, 1H ), 7.36 (d, J=8.1 Hz, 1H), 7.18 (t, J=7.2 Hz, 1H), 7.08 (t, J=7.1 Hz, 1H), 7.01 (t, J=7.1 Hz, 2H), 6.94 (d, J=2.2 Hz, 1H), 4.11 (t, J=6.3 Hz, 2H), 3, 91 (d, J=11.3 Hz, 2H), 2.82-2.72 (m, 1H), 2.68-2.32 (m, 12H), 2.31 (s, 3H), 2 .09 (dd, J=18.5, 7.0 Hz, 2H), 2.01 (dd, J=13.8, 6.9 Hz, 2H), 1.88 (dd, J=25.3 , 12.5, 3.8 Hz, 2H); 497 [M+H] ⁺ 58 N-(3-(2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.87 (s, 1H), 7.66 (d, J=8.9 Hz, 2H), 7.36 (d, J=7.8 Hz, 1H ), 7.24 (d, J=1.1 Hz, 1H), 7.10 (t, J=6.9 Hz, 1H), 7.04 (dd, J=10.8, 4.0 Hz , 1H), 6.90 (d, J=8.9 Hz, 2H), 4.17 (t, J=6.1 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H ), 2.95 (dd, J=13.3, 6.8 Hz, 2H), 2.69 (t, J=7.2 Hz, 2H), 2.55-2.37 (m, 10H) , 2.32 (s, 3H), 2.29 (s, 3H), 1.99 (dt, J=13.4, 6.6 Hz, 2H), 1.78 (p, J=7.0 Hz, 2H); 485 [M+H] ⁺ 59 N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.06 (s, 1H), 7.72 (d, J=8.9 Hz, 2H), 7.28-7.23 (m, 1H), 7 .10 (dd, J=9.6, 2.4 Hz, 1H), 7.00 (s, 1H), 6.92 (d, J=8.9 Hz, 2H), 4.25 (t, J=6.1 Hz, 1H), 3.99 (t, J=6.5 Hz, 2H), 3.01 (dd, J=13.3, 6.7 Hz, 2H), 2.88 ( d, J=11.0 Hz, 2H), 2.71 (t, J=7.2 Hz, 2H), 2.28 (s, 3H), 1.93 (t, J=10.4 Hz, 2H), 1.88-1.78 (m, 4H), 1.72 (d, J=9.8 Hz, 2H), 1.44-1.36 (m, 2H), 1.36-1 .24 (m, 3H); 488 [M+H] ⁺ 60 N-(3-(1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.04 (s, 1H), 7.72 (d, J=8.9 Hz, 2H), 7.49 (d, J=7.8 Hz, 1H ), 7.35 (d, J=8.1 Hz, 1H), 7.18 (t, J=7.2 Hz, 1H), 7.09 (t, J=7.1 Hz, 1H), 6.94 (d, J=2.1 Hz, 1H), 6.91 (d, J=8.9 Hz, 2H), 4.27 (t, J=6.1 Hz, 1H), 3, 99 (t, J=6.5 Hz, 2H), 3.01 (dd, J=13.3, 6.7 Hz, 2H), 2.87 (d, J=11.3 Hz, 2H), 2.77 (t, J=7.3 Hz, 2H), 2.27 (s, 3H), 1.98-1.88 (m, 2H), 1.88-1.84 (m, 2H) , 1.84-1.77 (m, 2H), 1.71 (d, J=9.3 Hz, 2H), 1.45-1.35 (m, 2H), 1.31-1.20 (m, 2H); 470 [M+H] ⁺ 61 N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.13 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.24 (s, 1H), 7.10 (dd , J=9.6, 2.4 Hz, 1H), 6.97 (s, 1H), 6.96-6.89 (m, 3H), 4.26 (s, 1H), 4.08 ( t, J=6.3 Hz, 2H), 3.00 (dd, J=12.7, 6.5 Hz, 2H), 2.91 (t, J=4.9 Hz, 4H), 2, 70 (t, J=7.3 Hz, 2H), 2.56-2.49 (m, 2H), 2.46 (s, 4H), 2.05-1.92 (m, 2H), 1 .87-1.76 (m, 2H); 475 [M+H] ⁺ 62 N-(3-(1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.11 (s, 1H), 7.53-7.47 (m, 2H), 7.36 (d, J=8.1 Hz, 1H), 7 .28 (s, 1H), 7.22-7.15 (m, 1H), 7.12-7.05 (m, 1H), 7.00-6.91 (m, 2H), 4.29 -4.21 (m, 1H), 4.15 (t, J=6.3 Hz, 2H), 3.02 (dd, J=13.3, 6.8 Hz, 2H), 2.77 ( t, J=7.1 Hz, 2H), 2.69-2.39 (m, 8H), 2.31 (s, 3H), 2.25-2.17 (m, 2H), 2.06 -1.95 (m, 2H), 1.88 (dt, J=14.1, 6.9 Hz, 2H); 489 [M+H] ⁺ 63 4-(3-(4-ethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.11 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.24 (s, 1H), 7.10 (dd , J=9.6, 2.3 Hz, 1H), 6.98-6.88 (m, 4H), 4.22 (t, J=6.2 Hz, 1H), 4.08 (t, J=6.3 Hz, 2H), 3.00 (dd, J=13.3, 6.8 Hz, 2H), 2.70 (t, J=7.2 Hz, 2H), 2.56- 2.39 (m, 10H), 2.03-1.96 (m, 2H), 1.86-1.77 (m, 2H), 1.10 (t, J=6.9 Hz, 3H) ; 503 [M+H] ⁺ 64 5-methoxy-3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)-sulfonyl)piperidin-4-yl)-1H-indole ^1H NMR (400 MHz, CDCl ₃ ) δ 7.91 (s, 1H), 7.74 (d, J=8.9 Hz, 2H), 7.24 (s, 1H), 7.01 (t , J=6.8 Hz, 2H), 6.93 (dd, J=7.2, 2.3 Hz, 2H), 6.85 (dd, J=8.8, 2.3 Hz, 1H) , 4.10 (t, J=6.3 Hz, 2H), 3.91 (d, J=11.8 Hz, 2H), 3.83 (s, 3H), 2.71 (t, J= 11.7 Hz, 1H), 2.66-2.37 (m, 12H), 2.31 (s, 3H), 2.07 (t, J=11.1 Hz, 2H), 2.04- 1.95 (m, 2H), 1.86 (ddd, J=25.6, 12.6, 3.8 Hz, 2H); 527 [M+H] ⁺ 65 5-methyl-3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)-sulfonyl)piperidin-4-yl)-1H-indole ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.91 (s, 1H), 7.74 (d, J=8.9 Hz, 2H), 7.32-7.21 (m, 3H), 7 .01 (dd, J=7.6, 5.5 Hz, 2H), 6.90 (d, J=2.2 Hz, 1H), 4.10 (t, J=6.3 Hz, 2H) , 3.91 (d, J=11.9 Hz, 2H), 2.78-2.67 (m, 1H), 2.65-2.44 (m, 10H), 2.47-2.39 (m, 5H), 2.32 (s, 3H), 2.08 (dd, J=15.6, 4.1 Hz, 2H), 2.01 (dd, J=13.8, 6.9 Hz, 2H), 1.88 (ddd, J=25.2, 12.5, 3.7 Hz, 2H); 511 [M+H] ⁺ 66 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.16 (s, 1H), 7.71 (d, J=8.8 Hz, 2H), 7.44 (d, J=1.6 Hz, 1H ), 7.28 (s, 1H), 7.13 (dd, J=8.7, 1.7 Hz, 1H), 6.97-6.89 (m, 3H), 4.22 (t, J=6.1 Hz, 1H), 4.08 (t, J=6.3 Hz, 2H), 3.00 (dd, J=13.4, 6.8 Hz, 2H), 2.71 ( t, J=7.2 Hz, 2H), 2.63-2.40 (m, 10H), 2.30 (s, 3H), 1.99 (dt, J=13.3, 6.5 Hz , 2H), 1.83 (dt, J=14.0, 7.0 Hz, 2H); 505 [M+H] ⁺ 67 N-(3-(5-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.99 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.32-7.22 (m, 2H), 7 .01 (d, J=8.1 Hz, 1H), 6.92 (d, J=8.8 Hz, 2H), 6.87 (d, J=1.8 Hz, 1H), 4.23 (t, J=6.1 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.00 (dd, J=13.1, 6.6 Hz, 2H), 2 .73 (t, J=7.2 Hz, 2H), 2.50 (ddd, J=14.0, 10.9, 5.9 Hz, 10H), 2.45 (s, 3H), 2, 30 (s, 3H), 2.00 (dd, J=13.8, 6.8 Hz, 2H), 1.84 (dd, J=14.2, 7.0 Hz, 2H); 485 [M+H] ⁺ 68 N-(3-(5-methoxy-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.99 (s, 1H), 7.70 (d, J=8.8 Hz, 2H), 7.23 (s, 1H), 6.97-6 .88 (m, 4H), 6.85 (dd, J=8.8, 2.3 Hz, 1H), 4.23 (t, J=6.2 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.85 (s, 3H), 3.01 (dd, J=13.2, 6.8 Hz, 2H), 2.73 (t, J=7.2 Hz, 2H), 2.68-2.36 (m, 10H), 2.30 (s, 3H), 1.99 (dt, J=13.4, 6.7 Hz, 2H), 1.86 (dt, J=14.0, 7.1 Hz, 2H); 501 [M+H] ⁺ 69 N-(3-(1H-indol-3-yl)propyl)-4-(3-(4-hydroxypiperidin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.12 (s, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.49 (d, J=8.0 Hz, 1H ), 7.35 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.2 Hz, 1H), 7.09 (t, J=7.1 Hz, 1H), 6.92 (d, J=8.8 Hz, 3H), 4.25 (t, J=6.2 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3, 73 (s, 1H), 3.00 (dd, J=13.3, 6.8 Hz, 2H), 2.80 (dd, J=23.9, 12.3, 5.4 Hz, 4H) , 2.52 (t, J=7.1 Hz, 2H), 2.24-2.11 (m, 2H), 2.04-1.96 (m, 2H), 1.95-1.80 (m, 4H), 1.66-1.59 (m, 2H); 472 [M+H] ⁺ 70 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.21 (s, 1H), 7.71 (d, J=8.7 Hz, 2H), 7.44 (d, J=1.3 Hz, 1H ), 7.28 (s, 1H), 7.13 (dd, J=8.5, 1.7 Hz, 1H), 6.94 (d, J=8.9 Hz, 3H), 4.24 (t, J=6.0 Hz, 1H), 4.08 (t, J=6.3 Hz, 2H), 2.99 (dd, J=13.4, 6.8 Hz, 2H), 2 .91 (t, J=4.8 Hz, 4H), 2.71 (t, J=7.2 Hz, 2H), 2.56-2.49 (m, 2H), 2.49-2, 36 (m, 4H), 2.04-1.94 (m, 2H), 1.83 (dt, J=13.9, 7.0 Hz, 2H); 491[M] 71 5-fluoro-3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)-sulfonyl)piperidin-4-yl)-1H-indole ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.03 (s, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.27 (d, J=8.7 Hz, 1H ), 7.13 (dd, J=9.7, 2.0 Hz, 1H), 7.02 (t, J=7.4 Hz, 2H), 6.99 (t, J=3.1 Hz , 1H), 6.93 (td, J=9.1, 2.2 Hz, 1H), 4.11 (t, J=6.3 Hz, 2H), 3.91 (d, J=11, 3 Hz, 2H), 2.73-2.65 (m, 1H), 2.63-2.34 (m, 12H), 2.31 (s, 3H), 2.03 (dt, J=14 ,1, 9.8 Hz, 4H), 1.84 (ddd, J=25.4, 12.5, 3.9 Hz, 2H); 502 [M+H] ⁺ 72 4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.15 (s, 1H), 7.71 (d, J=8.7 Hz, 2H), 7.30-7.22 (m, 1H), 7 .10 (dd, J=9.6, 2.1 Hz, 1H), 6.94 (dt, J=12.5, 3.0 Hz, 4H), 4.24 (t, J=6.2 Hz, 1H), 4.07 (t, J=6.2 Hz, 2H), 3.00 (dd, J=13.2, 6.6 Hz, 2H), 2.98-2.88 (m , 2H), 2.83 (d, J=10.7 Hz, 2H), 2.70 (t, J=7.2 Hz, 2H), 2.52 (t, J=7.3 Hz, 2H ), 2.01 (dt, J=12.6, 6.4 Hz, 2H), 1.82 (dt, J=13.8, 7.0 Hz, 2H), 1.07 (s, 3H) , 1.06 (s, 3H); 502[M] 73 N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-isobutyryl-piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.05 (s, 1H), 7.72 (d, J=8.8 Hz, 2H), 7.30-7.24 (m, 1H), 7 .09 (dd, J=9.6, 2.2 Hz, 1H), 7.00 (s, 1H), 6.97-6.89 (m, 3H), 4.25 (t, J=6 .4 Hz, 1H), 4.09 (t, J=6.2 Hz, 2H), 3.71-3.60 (m, 2H), 3.57-3.50 (m, 2H), 3 .01 (dd, J=13.4, 6.7 Hz, 2H), 2.79 (dt, J=13.6, 6.9 Hz, 1H), 2.70 (d, J=7.2 Hz, 2H), 2.55 (t, J=7.1 Hz, 2H), 2.51-2.38 (m, 4H), 2.05-1.93 (m, 2H), 1.87 -1.77 (m, 2H), 1.14 (s, 3H), 1.12 (s, 3H); 545 [M+H] ⁺ 74 N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.04 (s, 1H), 7.71 (d, J=8.7 Hz, 2H), 7.30-7.22 (m, 1H), 7 .10 (dd, J=9.6, 2.2 Hz, 1H), 6.99 (t, J=2.8 Hz, 1H), 6.94 (dd, J=11.7, 5.5 Hz, 3H), 4.24 (t, J=6.2 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.06-2.92 (m, 4H), 2.71 (t, J=7.1 Hz, 6H), 2.53 (t, J=7.1 Hz, 6H), 2.04-1.95 (m, 2H), 1.88-1 .76 (m, 2H); 557 [M+H] ⁺ 75 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-hydroxy-piperidin-1-yl)propoxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.19 (s, 1H), 7.71 (d, J=8.8 Hz, 2H), 7.44 (d, J=1.5 Hz, 1H ), 7.28 (s, 1H), 7.13 (dd, J=8.6, 1.8 Hz, 1H), 6.97-6.90 (m, 3H), 4.28-4, 19 (m, 1H), 4.08 (t, J=6.3 Hz, 2H), 3.78-3.67 (m, 1H), 3.49 (s, 1H), 2.99 (dd , J=13.3, 6.7 Hz, 2H), 2.85-2.76 (m, 2H), 2.71 (t, J=7.3 Hz, 2H), 2.57-2, 47 (m, 2H), 2.21-2.10 (m, 2H), 1.99 (dt, J=13.1, 6.5 Hz, 2H), 1.95-1.87 (m, 2H), 1.87-1.76 (m, 2H), 1.65-1.59 (m, 2H); 506[M] 76 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.10 (s, 1H), 7.71 (d, J=8.8 Hz, 2H), 7.44 (s, 1H), 7.28 (s , 1H), 7.14 (d, J=8.6 Hz, 1H), 6.97 (s, 1H), 6.93 (d, J=8.7 Hz, 2H), 4.25-4 .21 (m, 1H), 4.07 (t, J=6.2 Hz, 2H), 3.06-2.91 (m, 4H), 2.71 (t, J=7.1 Hz, 6H), 2.53 (s, 6H), 2.06-1.93 (m, 4H), 1.83 (dt, J=14.1, 7.1 Hz, 2H); 573[M] 77 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-(methylamino)-azetidin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.67 (s, 1H), 7.71 (d, J=8.8 Hz, 2H), 7.44 (s, 1H), 7.25 (s , 1H), 7.13 (d, J=7.3 Hz, 1H), 6.92 (d, J=8.7 Hz, 2H), 6.82 (s, 1H), 4.23 (t , J=6.4 Hz, 1H), 4.07 (t, J=6.2 Hz, 2H), 3.61 (t, J=6.8 Hz, 2H), 3.42-3.33 (m, 1H), 2.98 (dd, J=13.2, 6.6 Hz, 2H), 2.78 (t, J=6.5 Hz, 2H), 2.68 (t, J= 7.0 Hz, 2H), 2.64 (t, J=7.0 Hz, 2H), 2.37 (s, 3H), 1.90-1.83 (m, 2H), 1.79 ( dd, J=14.1, 7.0 Hz, 2H); 491[M] 78 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-chloropiperidin-1-yl)propoxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.11 (s, 1H), 7.71 (d, J=8.7 Hz, 2H), 7.44 (s, 1H), 7.28 (s , 1H), 7.14 (d, J=8.8 Hz, 1H), 6.97 (s, 1H), 6.93 (d, J=8.7 Hz, 2H), 4.24 (t , J=6.5 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.00 (dd, J=13.2, 6.6 Hz, 2H), 2.78 (s, 2H), 2.72 (t, J=7.2 Hz, 2H), 2.53 (t, J=7.2 Hz, 2H), 2.36-2.16 (m, 3H) , 2.14 -2.09 (s,2H), 2.03-1.94 (m, 2H), 1.94-1.87 (m, 2H), 1.87-1.78 (m, 2H); 524[M] 79 N-(3-(5-chloro-1H-indol-3-yl)propyl)-6-(3-(piperazin-1-yl)propoxy)pyridin-3-sulfonamide ¹ H NMR (400 MHz, MeOD) δ 8.56 (d, J=1.9 Hz, 1H), 8.01 (dd, J=8.7, 2.3 Hz, 1H), 7.42 ( s, 1H), 7.29 (d, J=8.6 Hz, 1H), 7.05 (d, J=8.3 Hz, 2H), 6.90 (d, J=8.8 Hz, 1H), 4.48 (t, J=5.9 Hz, 2H), 3.50 (d, J=4.4 Hz, 4H), 3.38 (s, 4H), 3.25-3, 14 (m, 2H), 2.95 (t, J=6.9 Hz, 2H), 2.71 (t, J=7.4 Hz, 2H), 2.22 (dd, J=12.8 , 6.7 Hz, 2H), 2.05 (d, J=5.5 Hz, 1H), 1.87-1.74 (m, 2H), 0.92 (t, J=6.6 Hz , 1H); 492.06[M] 80 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-fluoropiperidin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, MeOD) δ 7.72 (d, J=8.7 Hz, 2H), 7.42 (s, 1H), 7.29 (d, J=8.6 Hz, 1H) , 7.03 (dd, J=10.2, 8.0 Hz, 4H), 4.75 (s, 1H), 4.62 (s, 1H), 4.11 (t, J=6.1 Hz, 2H), 2.90 (t, J=7.0 Hz, 2H), 2.69 (t, J=7.3 Hz, 4H), 2.62-2.56 (m, 2H), 2.50 (s, 2H), 2.07-1.94 (m, 4H), 1.92-1.83 (m, 2H), 1.78 (dt, J=14.3, 7.2 Hz, 2H); 508[M] 81 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-(trifluoromethyl)-piperidin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.04 (s, 1H), 7.72 (d, J=8.7 Hz, 2H), 7.44 (s, 1H), 7.27 (d , J=7.9 Hz, 2H), 7.14 (d, J=8.7 Hz, 1H), 6.99 (s, 1H), 6.94 (d, J=8.8 Hz, 2H ), 4.24 (t, J=6.3 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.00 (dd, J=13.4, 6.6 Hz , 2H), 2.72 (t, J=7.2 Hz, 2H), 2.58 (t, J=6.9 Hz, 6H), 2.07-1.94 (m, 6H), 1 .85-1.78 (m, 2H); 558[M] 82 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,4-difluoro-piperidin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, MeOD) δ 7.73 (d, J=8.8 Hz, 2H), 7.42 (s, 1H), 7.29 (d, J=8.6 Hz, 1H) , 7.04 (dd, J=10.0, 7.3 Hz, 4H), 4.12 (t, J=6.2 Hz, 2H), 2.91 (t, J=6.9 Hz, 2H), 2.73-2.66 (m, 2H), 2.63 (t, J=7.3 Hz, 6H), 2.20 (dd, J=15.5, 7.0 Hz, 1H ), 2.10-1.94 (m, 6H), 1.84-1.73 (m, 2H); 526[M] 83 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-1,4-diazepan-1-yl)propoxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.37 (s, 1H), 7.71 (d, J=8.8 Hz, 2H), 7.44 (d, J=1.6 Hz, 1H ), 7.29-7.22 (m, 1H), 7.13 (dd, J=8.6, 1.8 Hz, 1H), 6.96-6.88 (m, 2H), 4, 33 (t, J=5.9 Hz, 1H), 4.08 (t, J=6.3 Hz, 2H), 3.00 (kv, J=6.5 Hz, 2H), 2.80- 2.73 (m, 4H), 2.69 (dd, J=14.4, 7.3 Hz, 4H), 2.66-2.59 (m, 4H), 2.37 (s, 3H) , 1.95 (dt, J=13.3, 6.5 Hz, 2H), 1.87-1.78 (m, 4H); 519[M] 84 N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.27 (br s, 1H), 7.70 (d, J =8.7 Hz, 2H), 7.29-7.21 (m, 1H) , 7.10 (dd, J =9.6, 2.0 Hz, 1H), 6.97-6.88 (m, 4H), 4.29 (t, J =6.2 Hz, 1H), 4.08 (t, J =6.3 Hz, 2H), 2.99 (kv, J =6.6 Hz, 2H), 2.69 (t, J =7.2 Hz, 2H), 2, 56-2.49 (m, 2H), 2.49-2.35 (m, 4H), 2.02 (p, J =13.3, 7.0 Hz, 2H), 1.82 (p, J =13.3, 7.0 Hz, 2H), 1.64-1.60 (m, 4H), 1.46 (s, 2H); 474 [M+H] ⁺ 85 N-(3-(1H-indol-3-yl)cyclohexyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.14 (br s, 1H), 7.80 (d, J =8.8 Hz, 2H), 7.47 (d, J =8.0 Hz , 1H), 7.34 (d, J =8.1 Hz, 1H), 7.17 (t, J =7.6 Hz, 1H), 7.06 (t, J =7.5 Hz, 1H ), 6.91 (d, J =8.8 Hz, 2H), 6.86-6.82 (m, 1H), 4.68 (d, J =6.9 Hz, 1H), 4.03 (t, J =6.3 Hz, 2H), 3.73-3.65 (m, 1H), 3.08-2.98 (m, 1H), 2.58-2.49 (m, 5H ), 2.31 (s, 3H), 2.06-1.92 (m, 4H), 1.74-1.63 (m, 4H), 1.62-1.51 (m, 2H); 511 [M+H] ⁺ 86 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)-naphthalene-1-sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.55 (d, J= 8.5 Hz, 1H), 8.37 (d, J= 8.3 Hz, 1H), 8.14 (d, J= 8 ,2 Hz, 2H), 7.66 (t, J= 7.7 Hz, 1H), 7.57 (t, J= 7.8 Hz, 1H), 7.31 (s, 1H), 7, 21 (d, J= 8.5 Hz, 1H), 7.10-7.08 (m, 1H), 6.76 (d, J= 8.4 Hz, 1H), 6.70 (s, 1H ), 4.52 (t, J= 6.2 Hz, 1H), 4.27 (t, J= 6.2 Hz, 2H), 2.91 (kv, J= 6.5 Hz, 2H), 2.64 (t, J= 7.2 Hz, 2H), 2.56-2.48 (m, 10H), 2.30 (s, 3H), 2.15 (p, J= 6.4 Hz , 2H), 1.72 (p, J= 7.0 Hz, 2H); 556 [M+H] ⁺ 87 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.33 (br s, 1H), 7.70 (d, J= 8.7 Hz, 2H), 7.44 (s, 1H), 7.26-7 .24 (m, 1H), 7.13-7.11 (m, 1H), 6.9 (d, J= 8.8 Hz, 3H), 4.28 (t, J= 6.2 Hz, 1H), 4.07 (t, J= 6.3 Hz, 2H), 2.98 (kv, J= 6.6 Hz, 2H), 2.69 (t, J= 7.2 Hz, 2H) , 2.49 (t, J= 7.2 Hz, 2H), 2.42 (br. s, 4H), 1.99 (p, J= 6.5 Hz, 2H), 1.83 (p, J= 7.0 Hz, 2H), 1.62-1.57 (m, 4H), 1.46-1.45 (m, 2H); 491 [M+H] ⁺ 88 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-4-yl)propyl)amino)-benzenesulfonamide ¹ H NMR 400 MHz, DMSO δ 10.97 (s, 1H), 7.50 (s, 1H), 7.43 (d, J= 8.6 Hz, 2H), 7.32 (d, J= 8.6 Hz, 1H), 7.15-7.13 (m, 2H), 7.05-7.03 (m, 1H), 6.59 (d, J= 8.7 Hz, 2H), 6.44 (t, J= 5.0 Hz, 1H), 3.02 (kv, J= 5.9 Hz, 2H), 2.92 (d, J= 11.7 Hz, 2H), 2, 71-2.68 (m, 2H), 2.60 (t, J= 7.4 Hz, 2H), 2.45-2.42 (m, 1H), 1.67 (p, J= 7, 1 Hz, 2H), 1.60-1.50 (m, 4H), 1.28-1.23 (m, 4H), 1.03-0.95 (m, 2H); 490 [M+H] ⁺ 89 N-(3-(1H-indol-3-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.57 (br. s, 1H), 7.73-7.71 (m, 3H), 7.42-7.40 (m, 2H), 7.33- 7.28 (m, 4H), 7.26-7.21 (m, 1H), 7.15 (t, J= 7.8 Hz, 1H), 7.00 (d, J= 8.1 Hz , 1H), 6.88 (d, J= 8.8 Hz, 2H), 4.01 (t, J= 6.3 Hz, 2H), 2.51-2.47 (m, 10H), 2 .29 (s, 3H), 1.94 (p, J= 6.9 Hz, 2H); 505 [M+H] ⁺ 90 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-1-yl)butyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 9.44 (br s, 1H), 7.66 (d, J =8.1 Hz, 2H), 7.48-7.43 (m, 1H) , 7.23 (d, J =8.4 Hz, 3H), 7.26-7.20 (m, 1H), 6.79-6.72 (m, 1H), 4.29 (t, J =6.1 Hz, 1H), 2.95 (kv, J =6.6 Hz, 2H), 2.69 (t, J =7.0 Hz, 4H), 2.58-2.39 (m , 4H), 2.39-2.31 (m, 2H), 1.85-1.76 (m, 2H), 1.68-1.58 (m, 6H), 1.54-1.40 (m, 4H); 488 [M+H] ⁺ 91 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperazin-1-yl)butyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.83 (br s, 1H), 7.69 (d, J =8.1 Hz, 2H), 7.47-7.42 (m, 1H) , 7.25-7.20 (m, 2H), 7.12 (dd, J =8.7, 1.6 Hz, 1H), 6.89-6.83 (m, 1H), 4.39 (broad s, 1H), 2.98 (t, J =6.7 Hz, 2H), 2.92 (t, J =4.8 Hz, 4H), 2.70 (t, J =6, 7 Hz, 4H), 2.57-2.40 (m, 4H), 2.40-2.32 (m, 2H), 1.99-1.84 (m, 4H), 1.84-1 .76 (m, 2H), 1.70-1.58 (m, 2H), 1.55-1.42 (m, 2H); 489 [M+H] ⁺ 92 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)-benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.16 (br s, 1H), 7.71 (d, J= 8.7 Hz, 2H), 7.44 (s, 1H), 7.28-7 .26 (m, 1H), 7.13 (d, J= 8.6 Hz, 1H), 6.99 (s, 1H), 6.92 (d, J= 8.7 Hz, 2H), 4 .29 (t, J= 5.8 Hz, 1H), 3.99 (t, J= 6.4 Hz, 2H), 2.99 (kv, J= 6.6 Hz, 2H), 2.91 (t, J= 10.8 Hz, 2H), 2.30 (s, 3H), 2.05-1.93 (m, 4H), 1.86-1.78 (m, 4H), 1, 72 (d, J= 9.4 Hz, 2H), 1.42-1.40 (m, 1H); 505 [M+H] ⁺ 93 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-4-yl)propoxy)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.13 (br s, 1H), 7.72 (d, J= 8.7 Hz, 2H), 7.45 (s, 1H), 7.28-7 .26 (m, 1H), 7.14 (d, J= 8.6 Hz, 1H), 6.99 (s, 1H), 6.93 (d, J= 8.7 Hz, 2H), 4 .31 (lat s, 1H), 3.99 (t, J= 6.4 Hz, 2H), 3.09 (d, J= 12.1 Hz, 2H), 3.00 (t, J= 6.6 Hz, 2H), 2.72 (t, J= 7.2 Hz, 2H), 2.60 (t, J= 11.8 Hz, 2H), 1.85-1.81 (m, 4H), 1.71 (d, J= 12.5 Hz, 4H), 1.41-1.38 (m, 3H), 1.19-1.10 (m, 1H); 491 [M+H] ⁺ 94 N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperidin-4-yl)propoxy)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.21 (br s, 1H), 7.44 (s, 1H), 7.39-7.37 (m, 2H), 7.32 (s, 1H) , 7.28-7.26 (m, 1H), 7.13 (d, J= 8.4 Hz, 1H), 7.08-7.07 (m, 1H), 6.99 (s, 1H ), 4.40 (lat s, 1H), 3.96 (t, J= 6.4 Hz, 2H), 3.09 (d, J= 12.1 Hz, 2H), 3.03 (t , J= 6.8 Hz, 2H), 2.73 (t, J= 7.2 Hz, 2H), 2.60 (t, J= 11.4 Hz, 2H), 1.88-1.77 (m, 4H), 1.72-1.69 (m, 4H), 1.40-1.37 (m, 3H), 1.19-1.10 (m, 1H); 491 [M+H] ⁺ 95 N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperidin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.97 (br s, 1H), 7.42-7.39 (m, 1H), 7.36-7.28 (m, 2H), 7. 25-7.22 (m, 2H), 7.14-7.09 (m, 1H), 7.01-6.96 (m, 1H), 6.94-6.91 (m, 1H), 4.36 (t, J =6.0 Hz, 1H), 4.01 (t, J =6.2 Hz, 2H), 2.98 (dd, J =13.2, 6.7 Hz, 2H ), 2.71 (t, J =7.0 Hz, 2H), 2.66-2.59 (m, 2H), 2.59-2.44 (m, 4H), 2.10-2, 00 (m, 2H), 1.87-1.80 (m, 2H), 1.71-1.56 (m, 4H), 1.54-1.42 (m, 2H).; 490 [M+H] ⁺ 96 N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.53 (br s, 1H), 7.44-7.40 (m, 1H), 7.38-7.31 (m, 2H), 7. 28 (s, 1H), 7.26-7.22 (m, 1H), 7.15-7.10 (m, 1H), 7.07-7.00 (m, 1H), 6.98- 6.94 (m, 1H), 4.40-4.28 (m, 1H), 4.03 (t, J =6.2 Hz, 2H), 3.06-2.95 (m, 2H) , 2.92 (t, J =4.8 Hz, 4H), 2.72 (t, J =7.1 Hz, 2H), 2.53 (t, J =7.2 Hz, 2H), 2 .51-2.40 (m, 4H), 1.99 (p, J =13.4, 6.7 Hz, 2H), 1.84 (p, J =13.7, 6.8 Hz, 2H ); 491 [M+H] ⁺ 97 N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperidin-4-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.19 (br s, 1H), 7.72 (d, J =8.7 Hz, 2H), 7.26-7.22 (m, 1H) , 7.09 (dd, J =9.6, 2.2 Hz, 1H), 6.99 (s, 1H), 6.95-6.88 (m, 3H), 3.98 (t, J =6.4 Hz, 2H), 3.09 (d, J =12.1 Hz, 2H), 2.99 (t, J =6.9 Hz, 2H), 2.70 (t, J =7 .2 Hz, 2H), 2.60 (t, J =11.5 Hz, 2H), 1.86-1.75 (m, 4H), 1.75-1.63 (m, 3H), 1 .45-1.30 (m, 2H), 1.30-1.20 (m, 1H), 1.19-1.05 (m, 2H); 474 [M+H] ⁺ 98 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methyl-piperazin-1-yl)propyl)amino)-benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.31 (br s, 1H), 7.57 (d, J= 8.7 Hz, 2H), 7.44 (d, J= 1.7 Hz, 1H ), 7.26-7.24 (m, 1H), 7.11 (dd, J= 8.6, 1.9 Hz, 1H), 6.95 (d, J= 1.9 Hz, 1H) , 6.52 (d, J= 8.8 Hz, 2H), 5.74 (lat s, 1H), 4.39 (t, J= 6.2 Hz, 1H), 3.23 (t, J= 6.2 Hz, 2H), 2.96 (kv, J= 6.5 Hz, 2H), 2.69 (t, J= 7.2 Hz, 2H), 2.53-2.50 ( m, 10H), 2.32 (s, 3H), 1.83-1.76 (m, 4H); 505 [M+H] ⁺ 99 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-4-yl)butyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.25 (br s, 1H), 7.70 (d, J =8.3 Hz, 2H), 7.43 (d, J =1.9 Hz , 1H), 7.28 (d, J =4.5 Hz, 2H), 7.26-7.24 (m, 1H), 7.13 (dd, J =8.6, 1.9 Hz, 1H), 6.98 (s, 1H), 3.10-3.03 (m, 2H), 3.01 (t, J =6.9 Hz, 2H), 2.71 (t, J =7 .2 Hz, 2H), 2.69-2.62 (m, 2H), 2.61-2.52 (m, 2H), 2.06-2.00 (m, 1H), 1.87- 1.78 (m, 4H), 1.66-1.56 (m, 2H), 1.36-1.18 (m, 4H), 1.14-1.02 (m, 2H); 488 [M+H] ⁺ 100 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyrrolidin-1-yl)propoxy)benzene sulfonamide ¹ H NMR 400 MHz, DMSO δ 10.94 (br s, 1H), 7.67 (d, J= 8.8 Hz, 2H), 7.48-7.44 (m, 2H), 7, 32 (d, J= 8.6 Hz, 1H), 7.12 (d, J= 1.5 Hz, 1H), 7.07-7.02 (m, 3H), 4.07 (t, J = 6.4 Hz, 2H), 2.75 (lat s, 2H), 2.60 (t, J= 7.4 Hz, 2H), 2.40 (lat s, 4H), 1.89 (p, J= 6.7 Hz, 2H), 1.71-1.63 (m, 6H); 477 [M+H] ⁺ 101 4-(3-(azepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.53 (br s, 1H), 7.70 (d, J =8.9 Hz, 2H), 7.42 (d, J =1.8 Hz , 1H), 7.26 (d, J =2.1 Hz, 1H), 7.10 (dd, J =8.6, 1.9 Hz, 1H), 6.89 (d, J =8, 8 Hz, 3H), 4.72-4.58 (m, 1H), 4.05 (t, J =6.2 Hz, 2H), 3.00-2.91 (m, 2H), 2, 80-2.71 (m, 6H), 2.67 (t, J =7.2 Hz, 2H), 2.06-1.97 (m, 2H), 1.79 (p, J =7, 0 Hz, 2H), 1.74-1.65 (m, 4H), 1.65-1.56 (m, 4H); 504 [M+H] ⁺ 102 4-(3-(1,4-diazepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, MeOD) δ 7.72 (d, J =8.9 Hz, 2H), 7.41-7.38 (m, 1H), 7.28 (d, J =8.6 Hz, 1H), 7.07-6.98 (m, 4H), 4.12 (t, J =6.1 Hz, 2H), 3.30-3.20 (m, 4H), 2.96 -2.86 (m, 4H), 2.84-2.73 (m, 4H), 2.67 (t, J =7.4 Hz, 2H), 2.02-1.93 (m, 4H ), 1.77 (n, J =14.4, 7.2 Hz, 2H); 505 [M+H] ⁺ 103 N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.20 (br s, 1H), 7.51-7.47 (m, 2H), 7.43 (d, J= 1.6 Hz, 1H), 7 ,26-7.25 (m, 1H), 7.12 (dd, J= 8.6, 1.9 Hz, 1H), 7.00 (d, J= 8.2 Hz, 1H), 6, 96-6.95 (m, 1H), 4.34 (t, J= 6.2 Hz, 1H), 4.14 (t, J= 6.3 Hz, 2H), 2.99 (kv, J = 6.5 Hz, 2H), 2.71 (t, J = 7.2 Hz, 2H), 2.56-2.47 (m, 10H), 2.28 (s, 3H), 2.02 (p, J= 6.6 Hz, 2H), 1.84 (p, J= 7.0 Hz, 2H); 524 [M+H] ⁺ 104 N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(piperazin-1-yl)propoxy)-benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.23 (br s, 1H), 7.52-7.48 (m, 2H), 7.44 (d, J= 1.7 Hz, 1H), 7 .27-7.24 (m, 1H), 7.12 (dd, J= 8.6, 1.8 Hz, 1H), 7.01-6.95 (m, 2H), 4.33 (lat .s, 1H), 4.15 (t, J= 6.3 Hz, 2H), 3.00 (lat s, 1H), 2.89 (t, J= 4.8 Hz, 4H), 2 .72 (t, J= 7.2 Hz, 2H), 2.52 (t, J= 7.1 Hz, 2H), 2.44 (lat s, 4H), 2.02 (p, J= 6.6 Hz, 2H), 1.84 (p, J= 7.0 Hz, 2H); 510 [M+H] ⁺ 105 N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-hydroxypiperidin-1-yl)propoxy)benzene sulfonamide ¹ H NMR 400 MHz, DMSO δ 10.95 (br s, 1H), 7.59-7.53 (m, 3H), 7.47 (d, J= 1.9 Hz, 1H), 7, 34-7.29 (m, 2H), 7.12 (d, J= 2.1 Hz, 1H), 7.03 (dd, J= 8.6, 2.0 Hz, 1H), 4.52 (d, J= 6.9 Hz, 1H), 4.14 (t, J= 6.4 Hz, 2H), 3.45-3.38 (m, 1H), 2.77 (sq, J= 6.3 Hz, 2H), 2.70-2.67 (m, 2H), 2.60 (t, J= 7.4 Hz, 2H), 2.37 (t, J= 7.0 Hz, 2H), 1.98 (t, J= 10.1 Hz, 2H), 1.88 (p, J= 6.5 Hz, 2H), 1.71-7.64 (m, 4H), 1, 40-1.31 (m, 2H); 525 [M+H] ⁺ 106 4-(3-(1,4-diazepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluorobenzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 10.95 (br s, 1H), 7.56-7.53 (m, 2H), 7.47 (d, J= 1.7 Hz, 1H), 7 ,34-7.30 (m, 2H), 7.12 (d, J= 1.7 Hz, 1H), 7.03 (dd, J= 8.6, 1.9 Hz, 1H), 4, 16 (t, J= 6.3 Hz, 2H), 2.79-2.70 (m, 6H), 2.63-2.54 (m, 9H), 1.86 (p, J= 6, 4 Hz, 2H), 1.71-1.59 (m, 4H); 524 [M+H] ⁺ 107 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.23 (br. s, 1H), 7.75-7.66 (m, 2H), 7.44 (d, J = 1.9 Hz, 1H) , 7.30-7.23 (m, 1H), 7.13 (dd, J = 8.6, 2.0 Hz, 1H), 6.96-6.87 (m, 3H), 4.35 -4.27 (m, 1H), 4.07 (t, J =6.3 Hz, 2H), 3.04-2.79 (m, 7H), 2.71 (t, J =7.2 Hz, 2H), 2.52 (t, J =7.3 Hz, 2H), 2.10-1.93 (m, 4H), 1.82 (p, J =14.1, 7.1 Hz , 2H), 1.06 (d, J =6.3 Hz, 3H); 505 [M+H] ⁺ 108 (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.23 (br s, 1H), 7.75-7.68 (m, 2H), 7.44 (d, J = 1.9 Hz, 1H) , 7.31-7.23 (m, 1H), 7.13 (dd, J =8.6, 1.9 Hz, 1H), 6.97-6.90 (m, 3H), 4.35 -4.26 (m, 1H), 4.07 (t, J =6.3 Hz, 2H), 3.05-2.78 (m, 7H), 2.71 (t, J =7.2 Hz, 2H), 2.52 (t, J =7.3 Hz, 2H), 2.08-1.95 (m, 3H), 1.82 (p, J =14.1, 7.1 Hz , 2H), 1.75-1.70 (m, 2H), 1.06 (d, J =6.3 Hz, 3H); 505 [M+H] ⁺ 109 (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.23 (br s, 1H), 7.74-7.67 (m, 2H), 7.44 (d, J = 1.9 Hz, 1H) , 7.28-7.23 (m, 1H), 7.13 (dd, J =8.6, 2.0 Hz, 1H), 6.97-6.90 (m, 3H), 4.37 -4.26 (m, 1H), 4.07 (t, J =6.3 Hz, 2H), 3.03-2.79 (m, 7H), 2.71 (t, J =7.2 Hz, 2H), 2.52 (t, J =7.3 Hz, 2H), 2.09-1.94 (m, 3H), 1.82 (p, J =7.0 Hz, 2H), 1.06 (d, J =6.3 Hz, 3H); 505 [M+H] ⁺ 110 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.26 (br. s, 1H), 7.75-7.68 (m, 2H), 7.44 (d, J = 1.9 Hz, 1H) , 7.27-7.24 (m, 1H), 7.13 (dd, J =8.6, 2.0 Hz, 1H), 6.98-6.89 (m, 3H), 4.35 (t, J =6.2 Hz, 1H), 4.07 (t, J =6.3 Hz, 2H), 3.03-2.89 (m, 4H), 2.85-2.78 ( m, 2H), 2.70 (t, J =7.2 Hz, 2H), 2.56-2.46 (m, 2H), 2.07-1.95 (m, 2H), 1.82 (n, J =7.1 Hz, 2H), 1.66-1.59 (m, 2H), 1.06 (d, J =6.4 Hz, 6H); 520 [M+H] ⁺ 111 (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3,4-dimethylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.53-8.32 (m, 1H), 7.71 (d, J =8.8 Hz, 2H), 7.42 (d, J =1, 3 Hz, 1H), 7.25 (d, J = 8.4 Hz, 1H), 7.10 (dd, J = 8.6, 1.8 Hz, 1H), 6.96-6.86 ( m, 3H), 4.76-4.54 (m, 1H), 4.04 (t, J =6.1 Hz, 2H), 3.03-2.92 (m, 3H), 2.92 -2.78 (m, 2H), 2.68 (t, J =7.2 Hz, 2H), 2.61-2.34 (m, 8H), 2.10 (t, J =10.7 Hz, 1H), 1.98 (p, J =13.3, 7.0 Hz, 2H), 1.81 (p, J =14.7, 7.0 Hz, 2H), 1.15 (d , J =6.3 Hz, 3H); 520 [M+H] ⁺ 112 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(4-methylpiperazin-1-yl)butyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.73 (br s, 1H), 7.68 (d, J =8.3 Hz, 2H), 7.45 (d, J =1.9 Hz , 1H), 7.26-7.23 (m, 2H), 7.13 (dd, J =8.6, 1.9 Hz, 1H), 6.86 (d, J =2.2 Hz, 1H), 4.34-4.24 (m, 1H), 2.99 (kv, J =6.7 Hz, 2H), 2.74-2.66 (m, 4H), 2.66-2 .40 (m, 8H), 2.41-2.35 (m, 2H), 2.29 (s, 3H), 1.83 (kV, J = 14.7, 7.0 Hz, 2H), 1.69-1.60 (m, 2H), 1.54-1.45 (m, 2H); 505 [M+H] ⁺ 113 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperazin-1-yl)propyl)amino)-benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.24 (br s, 1H), 7.57-7.55 (m, 2H), 7.44 (d, J= 1.9 Hz, 1H), 7 .25-7.23 (m, 2H), 7.11 (dd, J= 8.6, 2.0 Hz, 1H), 6.95 (s, 1H), 6.54-6.50 (m , 2H), 5.76 (br.s, 1H), 4.33 (br.s, 1H), 3.22 (t, J= 6.2 Hz, 2H), 2.98-2.91( m, 6H), 2.69 (t, J= 7.3 Hz, 2H), 2.50-2.45 (m, 6H), 1.84-1.71 (m, 4H); 491 [M+H] ⁺ 114 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-1-yl)propyl)amino)-benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.22 (br s, 1H), 7.57-7.55 (m, 2H), 7.45 (dd, J= 1.9 Hz, 1H), 7 ,25-7.23 (m, 2H), 7.11 (dd, J= 8.6, 2.0 Hz, 1H), 6.93 (d, J= 2.1 Hz, 1H), 6, 51 (d, J= 8.8 Hz, 2H), 4.24 (t, J= 6.3 Hz, 1H), 3.21 (t, J= 6.2 Hz, 2H), 2.96 ( d, J= 6.6 Hz, 2H), 2.69 (t, J= 7.3 Hz, 2H), 2.49-2.44 (m, 6H), 1.83-1.75 (m , 4H), 1.62 (p, J= 5.6 Hz, 4H), 1.49-1.48 (m, 2H); 490 [M+H] ⁺ 115 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(1-methylpiperidin-4-yl)butyl)-benzenesulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.70 (d, J = 8.3 Hz, 2H), 7.39 (d, J = 1.8 Hz, 1H), 7.33 (d, J = 8.2 Hz, 2H), 7.27 (d, J =8.6 Hz, 1H), 7.02 (dd, J =8.6, 2.0 Hz, 1H), 6.99 (s, 1H), 2.92 (t, J =7.0 Hz, 2H), 2.87-2.77 (m, 2H), 2.72-2.59 (m, 4H), 2.23 (s , 3H), 2.00-1.90 (m, 2H), 1.78-1.70 (m, 2H), 1.68-1.58 (m, 4H), 1.37-1.14 (m, 7H); 502 [M+H] ⁺ 116 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-((4-methyl-piperazin-1-yl)-methyl)cyclopropyl)methoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.25 (br s, 1H), 7.69 (d, J =8.8 Hz, 2H), 7.47-7.41 (m, 1H) , 7.26-7.22 (m, 1H), 7.16-7.10 (m, 1H), 7.00-6.88 (m, 3H), 4.30-4.21 (m, 1H), 3.94 (s, 2H), 2.99 (kv, J =6.7 Hz, 2H), 2.71 (t, J =7.2 Hz, 2H), 2.63-2, 38 (m, 8H), 2.38 (s, 2H), 2.27 (s, 3H), 1.88-1.78 (m, 2H), 0.65 (t, J =5.1 Hz , 2H), 0.48 (t, J =5.2 Hz, 2H); 531 [M+H] ⁺ 117 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-(piperazin-1-ylmethyl)cyclopropyl)-methoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.45 (br s, 1H), 7.72-7.65 (m, 2H), 7.44 (d, J = 1.8 Hz, 1H) , 7.26-7.22 (m, 1H), 7.13 (dd, J =8.6, 1.9 Hz, 1H), 6.97-6.93 (m, 2H), 6.91 (s, 1H), 4.45-4.21 (m, 1H), 3.94 (s, 2H), 2.98 (t, J =6.9 Hz, 2H), 2.85 (t, J =4.8 Hz, 4H), 2.70 (t, J =7.1 Hz, 2H), 2.52-2.39 (m, 4H), 2.36 (s, 2H), 1, 89-1.78 (m, 3H), 0.65 (t, J =5.3 Hz, 2H), 0.47 (t, J =5.4 Hz, 2H); 517 [M+H] ⁺ 118 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)phenoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.15 (br s, 1H), 7.73 (d, J =8.8 Hz, 2H), 7.46 (d, J =1.7 Hz , 1H), 7.29-7.22 (m, 4H), 7.13 (dd, J =8.6, 1.9 Hz, 1H), 7.04-6.97 (m, 3H), 6.77 (dd, J =8.3, 2.1 Hz, 1H), 6.60 (t, J =2.2 Hz, 1H), 6.51 (dd, J =7.9, 1, 8 Hz, 1H), 4.36 (t, J =6.2 Hz, 1H), 3.27-3.14 (m, 4H), 3.01 (kv, J =6.7 Hz, 2H) , 2.73 (t, J =7.2 Hz, 2H), 2.60-2.51 (m, 2H), 2.35 (s, 3H), 1.91-1.80 (m, 2H ),; 540 [M+H] ⁺ 119 4-(3-bromophenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.01 (br s, 1H), 7.81-7.74 (m, 2H), 7.46 (d, J = 1.8 Hz, 1H) , 7.37-7.32 (m, 1H), 7.30-7.23 (m, 3H), 7.21 (t, J =2.0 Hz, 1H), 7.13 (dd, J =8.6, 1.9 Hz, 1H), 7.06-6.96 (m, 4H), 4.40 (t, J =6.0 Hz, 1H), 3.03 (kv, J = 6.7 Hz, 2H), 2.74 (t, J =7.2 Hz, 2H), 1.87 (p, J =7.1 Hz, 2H); 521 [M+H] ⁺ 120 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)phenoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.06 (br. s, 1H), 7.77-7.69 (m, 2H), 7.46 (d, J = 1.8 Hz, 1H) , 7.26-7.21 (m, 2H), 7.13 (dd, J = 8.6, 1.9 Hz, 1H), 7.05-6.96 (m, 3H), 6.78 (dd, J =8.3, 2.1 Hz, 1H), 6.61 (t, J =2.2 Hz, 1H), 6.46 (dd, J =7.9, 1.8 Hz, 1H), 4.36 (t, J =6.3 Hz, 1H), 3.21-3.11 (m, 4H), 3.01 (kv, J =6.7 Hz, 2H), 2, 74 (t, J =7.2 Hz, 2H), 1.86 (p, J =14.1, 7.1 Hz, 2H), 1.72-1.64 (m, 4H), 1.64 -1.52 (m, 4H); 524 [M+H] ⁺ 121 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)phenoxy)benzene sulfonamide ^1H NMR (400 MHz, MeOD) δ 7.78-7.70 (m, 2H), 7.42 (d, J =1.8 Hz, 1H), 7.30-7.23 (m, 2H ), 7.02 (d, J =8.7 Hz, 4H), 6.83 (dd, J =8.3, 2.2 Hz, 1H), 6.64 (t, J =2.2 Hz , 1H), 6.49 (dd, J = 7.8, 1.8 Hz, 1H), 3.16-3.09 (m, 4H), 3.00-2.88 (m, 6H), 2.68 (t, J =7.4 Hz, 2H), 1.78 (p, J =14.4, 7.2 Hz, 2H); 525 [M+H] ⁺ 122 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-1,4-diazepan-1-yl)phenoxy)-benzenesulfonamide ^1H NMR (400 MHz, MeOD) δ 7.78-7.70 (m, 2H), 7.42 (d, J =1.8 Hz, 1H), 7.27 (d, J =8.6 Hz, 1H), 7.19 (t, J =8.2 Hz, 1H), 7.05-6.99 (m, 4H), 6.59 (dd, J =8.4, 2.2 Hz , 1H), 6.38 (t, J =2.2 Hz, 1H), 6.29 (dd, J =7.9, 1.7 Hz, 1H), 3.55-3.48 (m, 2H), 3.43 (t, J =6.3 Hz, 2H), 2.92 (t, J =7.0 Hz, 2H), 2.71-2.63 (m, 4H), 2, 60-2.53 (m, 2H), 2.34 (s, 3H), 2.00-1.92 (m, 2H), 1.78 (p, J = 14.5, 7.2 Hz, 2H); 553 [M+H] ⁺ 123 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methylpiperazin-1-yl)phenyl)amino)benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.09 (br s, 1H), 7.61 (d, J= 8.6 Hz, 2H), 7.44 (s, 1H), 7.23-7 .19 (m, 2H), 7.11 (d, J= 8.0 Hz, 1H), 6.97-6.95 (m, 3H), 6.68-6.63 (m, 3H), 6.01 (s, 1H), 4.29 (t, J= 6.2 Hz, 1H), 3.20-3.18 (m, 4H), 3.00 (kv, J= 6.0 Hz , 2H), 2.71 (t, J= 7.3 Hz, 2H), 2.57-2.55 (m, 4H), 2.34 (s, 3H), 1.82 (p, J= 7.1 Hz, 2H); 539 [M+H] ⁺ 124 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperazin-1-yl)phenyl)amino)benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.05 (br s, 1H), 7.61 (d, J= 8.8 Hz, 2H), 7.44 (d, J= 1.7 Hz, 1H ), 7.23-7.20 (m, 3H), 7.11 (dd, J= 8.6, 1.9 Hz, 1H), 6.97-6.95 (m, 3H), 6, 68-6.64 (m, 3H), 6.00 (s, 1H), 4.26 (t, J= 6.0 Hz, 1H), 3.14-3.12 (m, 4H), 3 .03-2.98 (m, 6H), 2.71 (t, J= 7.2 Hz, 2H), 1.82 (p, J= 7.1 Hz, 2H); 525 [M+H] ⁺ 125 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)pyrimidin-2-yl)amino)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.30 (br s, 1H), 8.01 (br s, 1H), 7.71 (d, J= 8.9 Hz, 2H), 7.66 (d, J= 8.9 Hz, 2H), 7.43 (d, J= 1.8 Hz, 1H), 7.37 (lat s, 1H), 7.21 (d, J= 8, 6 Hz, 1H), 7.09 (dd, J= 8.6, 1.9 Hz, 1H), 6.81 (d, J= 1.7 Hz, 1H), 6.11 (d, J= 5.8 Hz, 1H), 4.65 (lat s, 1H), 3.67-3.64 (m, 4H), 2.99-2.94 (m, 2H), 2.69 (t , J= 7.1 Hz, 2H), 2.49-2.47 (m, 4H), 2.34 (s, 3H), 1.82 (p, J= 6.9 Hz, 2H); 541 [M+H] ⁺ 126 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-morpholinophenyl)-amino)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.00 (br s, 1H), 7.63-7.61 (m, 2H), 7.44 (d, J= 2.0 Hz, 1H), 7 .26-7.21 (m, 2H), 7.12 (dd, J= 8.6, 2.0 Hz, 1H), 6.98-6.95 (m, 3H), 6.68-6 .64 (m, 3H), 6.01 (s, 1H), 4.26 (t, J= 6.3 Hz, 1H), 3.85-3.83 (m, 4H), 3.15- 3.13 (m, 4H), 3.01 (kv, J= 5.5 Hz, 2H), 2.71 (t, J= 7.2 Hz, 2H), 1.83 (p, J= 7 ,0 Hz, 2H); 526 [M+H] ⁺ 127 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(piperazin-1-yl)pyrimidin-2-yl)amino)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.26 (br s, 1H), 8.02 (d, J= 6.2 Hz, 1H), 7.72-7.70 (m, 2H), 7 ,67-7.65 (m, 2H), 7.44 (d, J= 1.8 Hz, 1H), 7.22 (d, J= 8.6 Hz, 1H), 7.13-7, 09 (m, 2H), 6.81 (d, J= 2.2 Hz, 1H), 6.11 (d, J= 6.2 Hz, 1H), 4.32 (lat s, 1H), 3.62 (t, J= 4.8 Hz, 4H), 3.00-2.94 (m, 6H), 2.71 (t, J= 7.1 Hz, 2H), 1.83 (p J= 7.0 Hz, 2H); 540 [M+H] ⁺ 128 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-morpholinophenoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.01 (br s, 1H), 7.77-7.71 (m, 2H), 7.46 (d, J = 1.9 Hz, 1H) , 7.30-7.24 (m, 2H), 7.13 (dd, J =8.6, 2.0 Hz, 1H), 7.07-6.97 (m, 3H), 6.75 (dd, J =8.3, 1.9 Hz, 1H), 6.59 (t, J =2.3 Hz, 1H), 6.56-6.50 (m, 1H), 4.38- 4.28 (m, 1H), 3.92-3.80 (m, 4H), 3.19-3.11 (m, 4H), 3.02 (kv, J =6.7 Hz, 2H) , 2.74 (t, J =7.3 Hz, 2H), 1.86 (p, J =7.1 Hz, 2H); 526 [M+H] ⁺ 129 4-(3-(1,4-diazepan-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.11 (br s, 1H), 7.77-7.68 (m, 2H), 7.46 (d, J = 1.9 Hz, 1H) , 7.27-7.24 (m, 2H), 7.20 (t, J =8.2 Hz, 1H), 7.13 (dd, J =8.6, 2.0 Hz, 1H), 7.05-7.00 (m, 2H), 7.00-6.97 (m, 1H), 6.54 (dd, J =8.4, 2.4 Hz, 1H), 6.37 ( t, J =2.3 Hz, 1H), 6.32 (dd, J =7.9, 1.7 Hz, 1H), 4.93-4.81 (m, 1H), 4.38-4 .26 (m, 1H), 3.61-3.46 (m, 4H), 3.06-2.98 (m, 4H), 2.91-2.82 (m, 2H), 2.74 (t, J =7.3 Hz, 2H), 1.94-1.82 (m, 4H); 539 [M+H] ⁺ 130 4-(3,5-bis(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.29 (br s, 1H), 7.72 (d, J =8.8 Hz, 2H), 7.46 (d, J =1.6 Hz , 1H), 7.24 (d, J =8.7 Hz, 1H), 7.12 (dd, J =8.6, 1.9 Hz, 1H), 7.02 (d, J =8, 8 Hz, 2H), 6.96 (s, 1H), 6.30 (s, 1H), 6.13 (d, J =1.9 Hz, 2H), 4.36-4.28 (m, 1H), 3.23-3.14 (m, 8H), 3.06-2.98 (m, 2H), 2.73 (t, J =7.2 Hz, 2H), 2.60-2 .51 (m, 8H), 2.34 (s, 6H), 1.89-1.81 (m, 2H); 637 [M+H] ⁺ 131 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.15 (br s, 1H), 7.70-7.68 (m, 2H), 7.48-7.39 (m, 4H), 7.22 ( d, J= 8.6 Hz, 1H), 7.10 (dd, J= 6.7 Hz, 1H), 6.90 (d, J= 2.1 Hz, 1H), 6.58 (s, 1H), 6.21 (dd, J= 12.1, 8.2 Hz, 2H), 4.41 (t, J= 6.2 Hz, 1H), 3.57-3.54 (m, 4H ), 3.00 (kv, J= 6.5 Hz, 2H), 2.70 (t, J= 7.2 Hz, 2H), 2.54-2.51 (m, 4H), 2.35 (s, 3H), 1.82 (p, J= 7.0 Hz, 2H); 540 [M+H] ⁺ 132 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-(piperazin-1-yl)pyridin-2-yl)amino)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.07 (br s, 1H), 7.71-7.69 (m, 2H), 7.50-7.40 (m, 4H), 7.25- 7.23 (m, 1H), 7.12 (dd, J= 8.6, 2.0 Hz, 1H), 6.92 (d, J= 2.1 Hz, 1H), 6.53 (s , 1H), 6.21 (dd, J= 11.6, 8.2 Hz, 2H), 4.25 (t, J= 6.1 Hz, 1H), 3.52-3.49 (m, 4H), 3.02-2.98 (m, 6H), 2.72 (t, J= 14.3 Hz, 2H), 2.04-2.02 (m, 1H), 1.84 (p , J= 7.0 Hz, 2H); 526 [M+H] ⁺ 133 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.86 (br s, 1H), 8.01 (d, J= 5.9 Hz, 1H), 7.68-7.65 (m, 2H), 7 ,43-7.37 (m, 3H), 7.20 (d, J= 8.6 Hz, 1H), 7.08 (dd, J= 8.6, 2.0 Hz, 1H), 6, 70 (broad s, 1H), 6.61 (d, J= 2.0 Hz, 2H), 6.41 (dd, J= 6.0, 2.0 Hz, 1H), 6.21 (s , 1H), 4.37 (br. s, 1H), 3.35-3.32 (m, 4H), 2.93 (t, J= 6.1 Hz, 2H), 2.68 (t, J= 7.0 Hz, 2H), 2.54-2.51 (m, 4H), 2.35 (s, 3H), 1.83 (p, J= 6.8 Hz, 2H); 540 [M+H] ⁺ 134 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(piperazin-1-yl)pyridin-2-yl)amino)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.86 (br s, 1H), 8.02 (d, J= 5.9 Hz, 1H), 7.68-7.66 (m, 2H), 7 .43-7.37 (m, 3H), 7.20 (d, J= 8.6 Hz, 1H), 7.09 (dd, J= 8.6, 1.9 Hz, 1H), 6, 66 (broad s, 1H), 6.61 (d, J= 1.9 Hz, 1H), 6.41 (dd, J= 6.1, 2.0 Hz, 1H), 6.21 (s , 1H), 4.27 (br. s, 1H), 3.30-3.28 (m, 4H), 3.01-2.99 (m, 4H), 2.94 (br. s, 2H ), 2.69 (t, J= 7.0 Hz, 2H), 1.83 (p, J= 6.8 Hz, 2H); 526 [M+H] ⁺ 135 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyrrolidin-1-yl)phenoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.00 (br s, 1H), 7.77-7.68 (m, 2H), 7.47 (d, J = 1.9 Hz, 1H) , 7.28-7.24 (m, 1H), 7.21 (t, J =8.1 Hz, 1H), 7.13 (dd, J =8.6, 1.9 Hz, 1H), 7.07-7.01 (m, 2H), 6.99 (d, J =2.2 Hz, 1H), 6.41 (dd, J =8.1, 2.0 Hz, 1H), 6 .31 (dd, J =8.0, 1.7 Hz, 1H), 6.24 (t, J =2.3 Hz, 1H), 4.32-4.25 (m, 1H), 3, 26 (t, J =6.6 Hz, 4H), 3.02 (kv, J =6.7 Hz, 2H), 2.74 (t, J =7.2 Hz, 2H), 2.03- 1.96 (m, 4H), 1.87 (p, J = 13.3, 7.0 Hz, 2H); 510 [M+H] ⁺ 136 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-hydroxypiperidin-1-yl)phenoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.04 (br s, 1H), 7.76-7.70 (m, 2H), 7.46 (d, J = 2.0 Hz, 1H) , 7.28-7.21 (m, 1H), 7.13 (dd, J =8.6, 2.0 Hz, 1H), 7.05-6.97 (m, 3H), 6.78 (dd, J =8.2, 2.1 Hz, 1H), 6.61 (t, J =2.3 Hz, 1H), 6.48 (dd, J =8.0, 1.6 Hz, 1H), 4.30 (t, J =6.3 Hz, 1H), 3.91-3.84 (m, 1H), 3.59-3.51 (m, 2H), 3.02 (kv , J =6.7 Hz, 2H), 2.96 (ddd, J =12.8, 9.8, 3.2 Hz, 2H), 2.74 (t, J =7.2 Hz, 2H) , 2.03-1.95 (m, 2H), 1.86 (p, J =7.1 Hz, 2H), 1.72-1.61 (m, 2H); 540 [M+H] ⁺ 137 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-fluoro-5-(4-methylpiperazin-1-yl)phenoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.05 (br. s, 1H), 7.79-7.73 (m, 2H), 7.46 (d, J = 1.8 Hz, 1H) , 7.30-7.23 (m, 1H), 7.13 (dd, J =8.6, 2.0 Hz, 1H), 7.07-7.01 (m, 2H), 6.99 (d, J =2.1 Hz, 1H), 6.43 (td, J =12.0, 2.0 Hz, 1H), 6.37-6.34 (m, 1H), 6.19 ( td, J =10.7, 2.0 Hz, 1H), 4.29 (t, J =6.3 Hz, 2H), 3.24-3.13 (m, 4H), 3.03 (kv , J =8.0 Hz, 2H), 2.74 (t, J =7.2 Hz, 2H), 2.58-2.47 (m, 4H), 2.34 (s, 2H), 1 .87 (n, J =14.7, 7.0 Hz, 2H); 557 [M+H] ⁺ 138 4-(3-bromo-5-(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.09 (br s, 1H), 7.78-7.72 (m, 2H), 7.46 (d, J = 1.9 Hz, 1H) , 7.28-7.23 (m, 1H), 7.15-7.10 (m, 1H), 7.05-7.00 (m, 2H), 6.99 (d, J =2, 1 Hz, 1H), 6.88-6.85 (m, 1H), 6.62 (t, J =1.8 Hz, 1H), 6.50 (t, J =2.1 Hz, 1H) , 4.44-4.33 (m, 1H), 3.24-3.17 (m, 4H), 3.03 (kv, J =6.7 Hz, 2H), 2.74 (t, J =7.2 Hz, 2H), 2.58-2.50 (m, 4H), 2.35 (s, 3H), 1.91-1.82 (m, 2H); 619 [M+H] ⁺ 139 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-hydroxypiperidin-1-yl)phenyl)amino)benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.09 (br s, 1H), 7.61 (d, J= 8.8 Hz, 2H), 7.44 (d, J= 1.4 Hz, 1H ), 7.24-7.18 (m, 2H), 7.10 (dd, J= 8.6, 1.8 Hz, 1H), 6.96-6.94 (m, 3H), 6, 69-6.67 (m, 2H), 6.62 (d, J= 7.3 Hz, 1H), 6.03 (s, 1H), 4.36 (t, J= 6.2 Hz, 1H ), 4.07-3.97 (m, 1H), 3.89-3.83 (m, 1H), 3.56-3.50 (m, 2H), 3.02-2.89 (m , 4H), 2.70 (t, J= 7.2 Hz, 2H), 2.00-1.96 (m, 2H), 1.81 (p, J= 7.0 Hz, 2H), 1 .71-1.54 (m, 2H); 540 [M+H] ⁺ 140 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-chloro-4-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)benzene- sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.31 (br s, 1H), 7.68 (d, J= 8.8 Hz, 2H), 7.43 (d, J= 1.8 Hz, 1H ), 7.37 (d, J= 8.8 Hz, 2H), 7.25-7.23 (m, 1H), 7.09 (dd, J= 6.6 Hz, 1H), 6.74 (d, J= 2.1 Hz, 1H), 6.69 (s, 1H), 6.37 (d, J= 1.8 Hz, 1H), 6.11 (d, J= 1.8 Hz , 1H), 5.29 (s, 1H), 4.40 (t, J= 6.1 Hz, 1H), 3.33-3.31 (m, 4H), 2.97 (p, J= 6.4 Hz, 2H), 2.69 (t, J= 7.0 Hz, 2H), 2.52-2.49 (m, 4H), 2.34 (s, 3H), 1.83 ( p, J= 6.8 Hz, 2H); 574 [M+H] ⁺ 141 4-((4,6-bis(4-methylpiperazin-1-yl)pyridin-2-yl)amino)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 8.24 (br s, 1H), 7.67 (d, J= 8.8 Hz, 2H), 7.43-7.40 (m, 3H), 7 .21 (d, J= 8.6 Hz, 1H), 7.09 (dd, J= 8.6, 2.0 Hz, 1H), 6.81 (d, J= 2.0 Hz, 1H) , 6.47 (lat s, 1H), 5.75-5.67 (m, 2H), 4.34 (t, J= 6.2 Hz, 1H), 3.52-3.49 (m , 4H), 3.30-3.27 (m, 4H), 2.98 (kv, J= 6.4 Hz, 2H), 2.69 (t, J= 7.1 Hz, 2H), 2 .50 (lat s, 8H), 2.33 (s, 6H), 1.81 (p, J= 6.9 Hz, 2H); 638 [M+H] ⁺ 142 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methyl-piperazin-1-yl)phenyl)amino)benzenesulfonamide ¹ H NMR 400 MHz, CDCl ₃ δ 10.93 (br s, 1H), 8.39 (br s, 1H), 7.50-7.48 (m, 3H), 7.31 (d, J= 8.6 Hz, 1H), 7.22 (t, J= 5.8 Hz, 1H), 7.13 (d, J= 1.8 Hz, 1H), 7.04-7.02 ( m, 3H), 6.91-6.87 (m, 4H), 3.09-3.06 (m, 4H), 2.73 (kv, J= 6.4 Hz, 2H), 2.61 (t, J= 7.4 Hz, 2H), 2.45-2.43 (m, 4H), 2.21 (s, 3H), 1.68 (p, J= 7.4 Hz, 2H) ; 539 [M+H] ⁺ 143 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)-benzamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.06 (br s, 1H), 7.60-7.53 (m, 3H), 7.31-7.27 (m, 1H), 7. 17-7.12 (m, 1H), 7.08 (s, 1H), 6.87 (d, J =8.7 Hz, 2H), 6.01-5.93 (m, 1H), 4 .04 (t, J =6.3 Hz, 2H), 3.52 (kv, J =6.6 Hz, 2H), 2.83 (t, J =7.2 Hz, 2H), 2.70 -2.40 (m, 10H), 2.33 (s, 3H), 2.05-1.96 (m, 4H); 469 [M+H] ⁺ 144 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzamide ^1H NMR (400 MHz, MeOD) δ 7.79-7.70 (m, 2H), 7.54-7.46 (m, 1H), 7.28 (d, J =8.6 Hz, 1H ), 7.12 (s, 1H), 7.03 (dd, J =8.6, 1.9 Hz, 1H), 6.99-6.91 (m, 2H), 4.54 (lat. s, 2H), 4.11 (t, J =6.1 Hz, 2H), 3.44 (t, J =7.1 Hz, 2H), 3.19-3.09 (m, 4H), 2.80 (t, J =7.3 Hz, 2H), 2.73-2.66 (m, 4H), 2.64 (t, J =7.2 Hz, 2H), 2.06-1 .94 (m, 4H); 455 [M+H] ⁺ 145 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(methylsulfonyl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.14 (br s, 1H), 7.75-7.68 (m, 2H), 7.42 (d, J=2.0 Hz, 1H) , 7.30-7.26 (m, 1H), 7.12 (dd, J=8.6, 2.1 Hz, 1H), 6.96-6.87 (m, 3H), 4.43 (t, J=6.2 Hz, 1H), 4.17 (t, J=5.8 Hz, 2H), 3.32-3.23 (m, 2H), 3.03-2.95 ( m, 5H), 2.69 (t, J=7.2 Hz, 2H), 2.44-2.34 (m, 2H), 1.81 (p, J=7.1 Hz, 2H); 486 [M+H] ⁺ 146 N-(3-(5-chloro-1H-indol-3-yl)propyl)-2-((3-(piperazin-1-yl)propyl)amino)-triazole-5-sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.17 (br s, 1H), 8.11 (br s, 1H), 7.57 (s, 1H), 7.50 (s, 1H) , 7.13 (d, J=7.7 Hz, 1H), 7.01 (s, 1H), 4.49 (lat s, 1H), 3.45-3.31 (m, 2H), 3.15-3.02 (m, 2H), 2.77 (t, J=7.2 Hz, 2H), 2.67-2.21 (m, 6H), 2.02-1.86 ( m, 2H), 1.86-1.73 (m, 2H), 1.68-1.44 (m, 4H); 497 [M+H] ⁺ 147 N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.93 (s, 1H), 7.66 (d, J=8.8 Hz, 2H), 7.31 (s, 1H), 7.16 (d , J=8.6 Hz, 1H), 7.05 (d, J=8.6 Hz, 1H), 6.92 (d, J=8.8 Hz, 2H), 4.15 (t, J =6.2 Hz, 1H), 4.07 (t, J=6.2 Hz, 2H), 2.93 (dd, J=13.3, 6.6 Hz, 2H), 2.70-2 .36 (m, 8H), 2.32 (s, 3H), 2.30 (s, 3H), 2.05-1.95 (m, 2H), 1.79-1.70 (m, 2H ), 1.70-1.50 (m, 4H); 519 [M+H] ⁺ 148 4-(4-(1H-imidazol-1-yl)butyl)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ¹ H NMR (400 MHz, DMSO) δ 10.95 (s, 1H), 7.67 (d, J=8.3 Hz, 2H), 7.59 (s, 1H), 7.55 (br. s, 1H), 7.47 (d, J=2.0 Hz, 1H), 7.36 (d, J=8.2 Hz, 2H), 7.32 (d, J=8.6 Hz, 1H), 7.12 (s, 1H), 7.11 (d, J=2.1 Hz, 1H), 7.04 (dd, J=8.6, 2.0 Hz, 1H), 6, 86 (s, 1H), 3.96 (t, J=7.0 Hz, 2H), 2.78 (t, J=6.5 Hz, 2H), 2.69-2.62 (m, 2H ), 2.59 (t, J=7.5 Hz, 2H), 1.75-1.60 (m, 4H), 1.56-1.43 (m, 2H); 471 [M+H] ⁺ 149 N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.17 (br s, 1H), 8.11 (br s, 1H), 7.57 (s, 1H), 7.50 (s, 1H) , 7.13 (d, J=7.7 Hz, 1H), 7.01 (s, 1H), 4.49 (lat s, 1H), 3.45-3.31 (m, 2H), 3.15-3.02 (m, 2H), 2.77 (t, J=7.2 Hz, 2H), 2.67-2.21 (m, 6H), 2.02-1.86 ( m, 2H), 1.86-1.73 (m, 2H), 1.68-1.44 (m, 4H); 497 [M+H] ⁺ 150 N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.93 (s, 1H), 7.66 (d, J=8.8 Hz, 2H), 7.31 (s, 1H), 7.16 (d , J=8.6 Hz, 1H), 7.05 (d, J=8.6 Hz, 1H), 6.92 (d, J=8.8 Hz, 2H), 4.15 (t, J =6.2 Hz, 1H), 4.07 (t, J=6.2 Hz, 2H), 2.93 (dd, J=13.3, 6.6 Hz, 2H), 2.70-2 .36 (m, 8H), 2.32 (s, 3H), 2.30 (s, 3H), 2.05-1.95 (m, 2H), 1.79-1.70 (m, 2H ), 1.70-1.50 (m, 4H); 519 [M+H] ⁺ 151 N-(4-(5-chloro-1H-indol-3-yl)butan-2-yl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, DMSO) δ 10.95 (s, 1H), 7.67 (d, J=8.3 Hz, 2H), 7.59 (s, 1H), 7.55 (br. s, 1H), 7.47 (d, J=2.0 Hz, 1H), 7.36 (d, J=8.2 Hz, 2H), 7.32 (d, J=8.6 Hz, 1H), 7.12 (s, 1H), 7.11 (d, J=2.1 Hz, 1H), 7.04 (dd, J=8.6, 2.0 Hz, 1H), 6, 86 (s, 1H), 3.96 (t, J=7.0 Hz, 2H), 2.78 (t, J=6.5 Hz, 2H), 2.69-2.62 (m, 2H ), 2.59 (t, J=7.5 Hz, 2H), 1.75-1.60 (m, 4H), 1.56-1.43 (m, 2H); 471 [M+H] ⁺ 152 N-(4-(5-chloro-1H-indol-3-yl)butan-2-yl)-4-(3-(piperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.28 (br s, 1H), 7.50-7.42 (m, 3H), 7.29 (d, J=8.6 Hz, 1H) , 7.24 (dd, J=7.9, 1.7 Hz, 1H), 7.21-7.11 (m, 4H), 6.83-6.76 (m, 2H), 6.75 (d, J=2.3 Hz, 1H), 6.45 (br s, 1H), 4.05 (t, J=6.3 Hz, 2H), 3.67 (s, 2H), 2 .77-2.33 (m, 10H), 2.30 (s, 3H), 2.03-1.95 (m, 2H); 553 [M+H] ⁺ 153 N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.44 (br s, 1H), 7.80-7.66 (m, 2H), 7.64-7.54 (m, 1H), 7. 26-7.18 (m, 2H), 6.96-6.88 (m, 3H), 4.64 (lat s, 1H), 4.06 (t, J=6.3 Hz, 2H) , 2.97 (t, J=6.9 Hz, 2H), 2.90 (t, J=4.9 Hz, 4H), 2.69 (t, J=7.2 Hz, 2H), 2 .59-2.35 (m, 6H), 2.05-1.93 (m, 2H), 1.90-1.78 (m, 3H); 536 [M+H] ⁺ 154 N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.48 (br s, 1H), 7.75-7.67 (m, 2H), 7.63-7.56 (m, 1H), 7. 25-7.18 (m, 2H), 6.95-6.88 (m, 3H), 4.67 (t, J=6.2 Hz, 1H), 4.05 (t, J=6, 3 Hz, 2H), 2.96 (kv, J=6.5 Hz, 2H), 2.68 (t, J=7.2 Hz, 2H), 2.60-2.41 (m, 8H) , 2.29 (s, 3H), 2.08 (br s, 1H), 2.04-1.91 (m, 3H), 1.80 (p, J=7.1 Hz, 2H); 550 [M+H] ⁺ 155 N-(3-(5-phenyl-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.21 (br s, 1H), 7.71-7.66 (m, 3H), 7.66-7.61 (m, 2H), 7. 47-7.39 (m, 4H), 7.34-7.28 (m, 1H), 6.96 (s, 1H), 6.88-6.83 (m, 2H), 4.36 ( lat.s, 1H), 3.99 (t, J=6.2 Hz, 2H), 3.05-2.99 (m, 2H), 2.96 (t, J=4.9 Hz, 4H ), 2.80 (t, J=7.2 Hz, 2H), 2.57-2.44 (m, 6H), 1.99-1.91 (m, 3H), 1.90-1, 83 (m, 2H); 533 [M+H] ⁺ 156 4-(3-(4-methylpiperazin-1-yl)propoxy)-N-(3-(5-phenyl-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.21 (br s, 1H), 7.72-7.66 (m, 3H), 7.66-7.61 (m, 2H), 7. 48-7.39 (m, 4H), 7.32 (t, J=7.4 Hz, 1H), 6.98-6.94 (m, 1H), 6.90-6.83 (m, 2H), 4.32 (t, J=6.3 Hz, 1H), 4.00 (t, J=6.4 Hz, 2H), 3.02 (kv, J=6.6 Hz, 2H) , 2.80 (t, J=7.2 Hz, 2H), 2.69-2.34 (m, 10H), 2.30 (s, 3H), 1.96 (p, J=6.7 Hz, 2H), 1.88 (p, J=7.0 Hz, 2H); 547 [M+H] ⁺ 157 N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 7.99 (br s, 1H), 7.70-7.62 (m, 2H), 7.30 (d, J=1.9 Hz, 1H) , 7.16 (d, J=8.5 Hz, 1H), 7.04 (dd, J=8.5, 2.0 Hz, 1H), 6.96-6.88 (m, 2H), 4.23 (lat s, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.00-2.79 (m, 6H), 2.64 (t, J=7, 2 Hz, 2H), 2.56-2.37 (m, 6H), 2.32 (s, 3H), 2.06-1.94 (m, 2H), 1.80-1.67 (m , 6H); 505 [M+H] ⁺ 158 N-(2-(5-chloro-1H-indol-3-yl)-ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)-benzenesulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.17 (s, 1H), 7.68-7.60 (m, 2H), 7.32 (d, J=1.9 Hz, 1H), 7 ,28-7.25 (m, 1H), 7.13 (dd, J=8.6, 2.0 Hz, 1H), 7.01 (d, J=2.3 Hz, 1H), 6, 92-6.84 (m, 2H), 4.27 (t, J=6.1 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.25 (kv, J =6.5 Hz, 2H), 2.88 (t, J=6.6 Hz, 2H), 2.69-2.32 (m, 10H), 2.29 (s, 3H), 2.05 -1.93 (m, 2H); 491 [M+H] ⁺ 159 N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.22 (br s, 1H), 7.64 (d, J=8.8 Hz, 2H), 7.32 (d, J=1.7 Hz , 1H), 7.28-7.24 (m, 1H), 7.13 (dd, J=8.6, 1.8 Hz, 1H), 7.01 (s, 1H), 6.88 ( d, J=8.8 Hz, 2H), 4.30 (lat s, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.25 (t, J=6.4 Hz, 2H), 3.01-2.80 (m, 6H), 2.55-2.42 (m, 6H), 2.00 (dt, J=13.3, 6.5 Hz, 2H) ; 477 [M+H] ⁺ 160 4-(3-(1H-1,2,4-triazol-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.44 (br s, 1H), 8.01 (d, J=18.3 Hz, 2H), 7.77-7.68 (m, 2H) , 7.44 (d, J=2.0 Hz, 1H), 7.27-7.24 (m, 1H), 7.12 (dd, J=8.6, 2.0 Hz, 1H), 6.92-6.86 (m, 3H), 4.44 (t, J=6.5 Hz, 2H), 4.32 (t, J=6.1 Hz, 1H), 3.95 (t , J=5.7 Hz, 2H), 3.03-2.94 (m, 2H), 2.70 (t, J=7.2 Hz, 2H), 2.44-2.37 (m, 2H), 1.82 (p, J=7.0 Hz, 2H); 474 [M+H] ⁺ 161 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(2-methyl-1H-imidazol-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, MeOD) δ 7.71 (d, J=1.9 Hz, 2H), 7.39 (d, J=2.0 Hz, 1H), 7.34 (s, 1H) , 7.27 (d, J=8.6 Hz, 1H), 7.21 (lat s, 1H), 7.06-6.95 (m, 4H), 4.29 (t, J=6 .8 Hz, 2H), 4.07 (t, J=5.5 Hz, 2H), 2.90 (t, J=7.0 Hz, 2H), 2.67 (t, J=7.4 Hz, 2H), 2.50 (s, 3H), 2.31 (p, J=12.3, 6.2 Hz, 2H), 1.76 (p, J=14.4, 7.2 Hz , 2H); 487 [M+H] ⁺ 162 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-3-oxopiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.26 (br s, 1H), 7.74-7.68 (m, 2H), 7.46-7.42 (m, 1H), 7. 28-7.26 (m, 1H), 7.13 (dd, J=8.6, 2.0 Hz, 1H), 6.97-6.88 (m, 3H), 4.29 (t, J=6.3 Hz, 1H), 4.08 (t, J=6.1 Hz, 2H), 3.35-3.30 (m, 2H), 3.15 (s, 2H), 3, 04-2.93 (m, 5H), 2.74-2.67 (m, 4H), 2.58 (t, J=6.9 Hz, 2H), 1.98 (p, J=6, 5 Hz, 2H), 1.82 (p, J=7.1 Hz, 2H); 520 [M+H] ⁺ 163 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-oxopiperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.17 (br s, 1H), 7.76-7.68 (m, 2H), 7.46-7.42 (m, 1H), 7. 29-7.26 (m, 1H), 7.16-7.10 (m, 1H), 6.97-6.90 (m, 3H), 5.77 (s, 1H), 4.29 ( t, J=6.3 Hz, 1H), 4.09 (t, J=6.2 Hz, 2H), 3.41-3.35 (m, 2H), 3.17 (s, 2H), 3.00 (kv, J=6.7 Hz, 2H), 2.74-2.67 (m, 4H), 2.62 (t, J=6.9 Hz, 2H), 1.99 (p , J=6.5 Hz, 2H), 1.82 (p, J=7.1 Hz, 2H); 506 [M+H] ⁺ 164 N-(3-(5,7-dichloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.45 (br s, 1H), 7.76-7.67 (m, 2H), 7.39-7.33 (m, 1H), 7. 21-7.15 (m, 1H), 7.02 (s, 1H), 6.96-6.89 (m, 2H), 4.43 (s, 1H), 4.06 (t, J= 6.3 Hz, 2H), 3.48 (s, 1H), 2.97 (t, J=6.9 Hz, 2H), 2.90 (t, J=4.9 Hz, 4H), 2 .70 (m, J=7.3, 0.9 Hz, 2H), 2.54-2.34 (m, 6H), 2.05-1.93 (m, 2H), 1.82 (p , J=7.1 Hz, 2H); 526 [M+H] ⁺ 165 N-(3-(5,7-dichloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.30 (br s, 1H), 7.76-7.68 (m, 2H), 7.40-7.34 (m, 1H), 7. 21-7.16 (m, 1H), 7.05-7.01 (m, 1H), 6.97-6.89 (m, 2H), 4.31 (t, J=6.3 Hz, 1H), 4.07 (t, J=6.4 Hz, 2H), 2.98 (kv, J=6.7 Hz, 2H), 2.75-2.67 (m, 2H), 2, 64-2.33 (m, 10H), 2.29 (s, 3H), 2.06-1.93 (m, 2H), 1.83 (p, J=7.1 Hz, 2H); 540 [M+H] ⁺ 166 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,5-dichloro-1H-imidazol-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.60 (br s, 1H), 7.78-7.69 (m, 2H), 7.44 (d, J=2.0 Hz, 1H) , 7.29 (d, J=5.6 Hz, 1H), 7.12 (dd, J=8.6, 2.0 Hz, 1H), 6.94-6.87 (m, 2H), 6.85 (d, J=2.3 Hz, 1H), 4.30 (t, J=6.2 Hz, 1H), 4.20 (t, J=6.5 Hz, 2H), 3, 93 (t, J=5.6 Hz, 2H), 3.00 (kv, J=6.8 Hz, 2H), 2.70 (t, J=7.1 Hz, 2H), 2.33- 2.22 (m, 2H), 1.82 (p, J=7.0 Hz, 2H); 541 [M+H] ⁺ 167 N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.74-7.67 (m, 2H), 7.57 (dd, J=1.8, 0.6 Hz, 1H), 7.37 (dd, J=8.8, 0.6 Hz, 1H), 7.32 (dd, J=8.8, 1.8 Hz, 1H), 6.92-6.84 (m, 2H), 5.22 -5.13 (m, 1H), 4.05 (t, J=6.3 Hz, 2H), 3.05 (kv, J=6.5 Hz, 2H), 2.93 (t, J= 7.1 Hz, 2H), 2.67-2.38 (m, 10H), 2.32 (s, 3H), 2.04-1.90 (m, 4H); 506 [M+H] ⁺ 168 N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.74-7.66 (m, 2H), 7.57 (d, J=1.1 Hz, 1H), 7.40-7.30 (m, 2H), 6.93-6.84 (m, 2H), 4.06 (t, J=6.3 Hz, 2H), 3.05 (t, J=6.7 Hz, 2H), 2, 96-2.88 (m, 6H), 2.55-2.40 (m, 6H), 2.03-1.98 (m, 4H); 492 [M+H] ⁺ 169 N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 9.02 (br s, 1H), 8.21 (d, J=2.2 Hz, 1H), 7.76 (d, J=2.2 Hz , 1H), 7.75-7.68 (m, 2H), 7.00 (d, J=1.9 Hz, 1H), 6.95-6.86 (m, 2H), 4.42 ( t, J=6.2 Hz, 1H), 4.08 (t, J=6.2 Hz, 2H), 2.98 (dd, J=13.1, 6.7 Hz, 2H), 2, 76-2.57 (m, 10H), 2.43 (s, 3H), 2.06-1.97 (m, 2H), 1.87-1.79 (m, 2H); 506 [M+H] ⁺ 170 N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 8.21 (d, J=2.2 Hz, 1H), 7.77 (d, J=2.2 Hz, 1H), 7.75-7.68 (m, 2H), 7.02 (s, 1H), 6.94-6.86 (m, 2H), 4.42 (lat s, 1H), 4.08 (t, J=6.2 Hz, 2H), 3.03-2.94 (m, 4H), 2.70 (t, J=7.3 Hz, 2H), 2.60-2.53 (m, 4H), 2.06 -1.95 (m, 2H), 1.90-1.75 (m, 6H); 492 [M+H] ⁺ 171 (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.18 (s, 1H), 7.76-7.68 (m, 2H), 7.47-7.40 (m, 1H), 7.27- 7.24 (m, 1H), 7.12 (dd, J=8.6, 2.0 Hz, 1H), 6.99-6.93 (m, 2H), 6.93-6.88 ( m, 1H), 4.38 (t, J=6.0 Hz, 1H), 4.16-4.08 (m, 1H), 4.08-3.98 (m, 2H), 2.98 (kv, J=6.5 Hz, 2H), 2.81-2.65 (m, 4H), 2.64-2.37 (m, 8H), 2.32 (s, 3H), 1, 81 (p, J=7.0 Hz, 2H); 522 [M+H] ⁺ 172 (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.12 (br s, 1H), 7.76-7.67 (m, 2H), 7.46-7.42 (m, 1H), 7. 28-7.24 (m, 1H), 7.13 (dd, J=8.6, 2.0 Hz, 1H), 7.00-6.94 (m, 2H), 6.93-6, 89 (m, 1H), 4.26 (lat s, 1H), 4.16-4.09 (m, 1H), 4.09-3.99 (m, 2H), 3.04-2, 96 (m, 2H), 2.96-2.87 (m, 4H), 2.74-2.62 (m, 4H), 2.59-2.51 (m, 2H), 2.49- 2.39 (m, 2H), 1.82 (p, J=7.0 Hz, 2H); 508 [M+H] ⁺ 173 (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.17 (br s, 1H), 7.76-7.67 (m, 2H), 7.47-7.40 (m, 1H), 7. 28-7.23 (m, 1H), 7.12 (dd, J=8.6, 2.0 Hz, 1H), 6.99-6.92 (m, 2H), 6.91 (d, J=2.4 Hz, 1H), 4.36 (t, J=6.3 Hz, 1H), 4.16-4.07 (m, 1H), 4.07-3.98 (m, 2H ), 2.98 (kv, J=6.6 Hz, 2H), 2.81-2.66 (m, 4H), 2.64-2.38 (m, 8H), 2.32 (s, 3H), 1.81 (p, J=7.0 Hz, 2H); 522 [M+H] ⁺ 174 (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.15 (br s, 1H), 7.75-7.68 (m, 2H), 7.46-7.41 (m, 1H), 7. 27-7.24 (m, 1H), 7.13 (dd, J=8.6, 2.0 Hz, 1H), 6.99-6.93 (m, 2H), 6.92-6, 89 (m, 1H), 4.32 (br. s, 1H), 4.17-4.09 (m, 1H), 4.08-3.99 (m, 2H), 3.03-2, 90 (m, 6H), 2.73-2.63 (m, 4H), 2.56-2.51 (m, 2H), 2.48-2.39 (m, 2H), 1.82 ( p, J=7.0 Hz, 2H); 508 [M+H] ⁺ 175 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,5-dimethyl-1H-imidazol-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 9.97 (br s, 1H), 7.75-7.68 (m, 2H), 7.44 (d, J=1.9 Hz, 1H) , 7.26-7.21 (m, 2H), 7.08 (dd, J=8.6, 2.0 Hz, 1H), 6.90-6.82 (m, 2H), 6.70 (d, J=1.7 Hz, 1H), 4.38 (lat s, 1H), 4.10 (t, J=6.4 Hz, 2H), 3.84 (t, J=5, 5 Hz, 2H), 3.01-2.91 (m, 2H), 2.69 (t, J=7.0 Hz, 2H), 2.23-2.10 (m, 8H), 1, 80-1.77 (m, 2H); 501 [M+H] ⁺ 176 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(2,4,5-trimethyl-1H-imidazol-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 9.31 (br s, 1H), 7.75-7.67 (m, 2H), 7.44 (d, J=1.9 Hz, 1H) , 7.24-7.21 (m, 1H), 7.10 (dd, J=8.6, 2.0 Hz, 1H), 6.88-6.81 (m, 3H), 4.29 (t, J=6.2 Hz, 1H), 4.00 (t, J=6.7 Hz, 2H), 3.87 (t, J=5.5 Hz, 2H), 2.97 (kv , J=6.7 Hz, 2H), 2.69 (t, J=7.1 Hz, 2H), 2.21 (s, 3H), 2.18-2.07 (m, 8H), 1 .84-1.74 (m, 2H); 515 [M+H] ⁺ 177 N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.86-7.76 (m, 3H), 7.32 (d, J=1.9 Hz, 1H), 7.16 (d, J=8, 5 Hz, 1H), 7.05 (dd, J=8.5, 2.0 Hz, 1H), 7.01-6.94 (m, 2H), 4.54-4.46 (m, 1H ), 4.07 (t, J=6.3 Hz, 2H), 3.09-2.94 (m, 2H), 2.79-2.68 (m, 3H), 2.64-2, 33 (m, 9H), 2.29 (s, 3H), 2.27-2.14 (m, 1H), 2.07-1.91 (m, 4H); 531 [M+H] ⁺ 178 N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.88-7.76 (m, 3H), 7.32 (d, J=1.9 Hz, 1H), 7.16 (d, J=8, 5 Hz, 1H), 7.05 (dd, J=8.5, 2.0 Hz, 1H), 7.01-6.94 (m, J=8.9 Hz, 2H), 4.49 ( lat.s, 1H), 4.08 (t, J=6.3 Hz, 2H), 3.06-2.97 (m, 2H), 2.90 (t, J=4.9 Hz, 4H ), 2.78-2.68 (m, 3H), 2.54-2.37 (m, 6H), 2.26-2.18 (m, 1H), 2.07-1.93 (m , 4H); 517 [M+H] ⁺ 179 N-(3-(5-chloro-1H-indol-3-yl)cyclohexyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.81-7.74 (m, 2H), 7.46 (d, J=1.9 Hz, 1H), 7.27 (d, J=8.6 Hz, 1H), 7.02 (dd, J=8.6, 2.0 Hz, 1H), 7.00-6.93 (m, 3H), 4.03 (t, J=6.1 Hz , 2H), 3.57-3.47 (m, 1H), 3.16-3.06 (m, 1H), 2.74-2.50 (m, 8H), 2.39 (s, 3H ), 2.02-1.91 (m, 4H), 1.87-1.80 (m, 1H), 1.78-1.68 (m, 1H), 1.67-1.52 (m , 5H); 545 [M+H] ⁺ 180 N-(3-(5-chloro-1H-indol-3-yl)cyclohexyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.78 (d, J=8.9 Hz, 2H), 7.46 (d, J=1.9 Hz, 1H), 7.27 (d, J= 8.6 Hz, 1H), 7.02 (dd, J=8.6, 2.0 Hz, 1H), 7.00-6.92 (m, 3H), 4.04 (t, J=6 ,1 Hz, 2H), 3.53-3.48 (m, 1H), 3.15-3.10 (m, 1H), 2.97 (t, J=5.0 Hz, 4H), 2 .63-2.44 (m, 6H), 2.01-1.91 (m, 3H), 1.87-1.80 (m, 1H), 1.77-1.69 (m, 1H) , 1.67-1.53 (m, 5H).; 531 [M+H] ⁺ 181 N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.69-7.63 (m, 1H), 7.56 (s, 1H), 7.45 (d, J=8.7 Hz, 1H), 7, 28-7.22 (m, 1H), 7.18-7.07 (m, 3H), 6.82-6.76 (m, 2H), 6.63-6.55 (m, 2H), 6.49 (d, J=1.9 Hz, 1H), 4.02 (t, J=6.1 Hz, 2H), 2.86-2.35 (m, 10H), 2.31 (s , 3H), 2.02-1.92 (m, 2H); 583 [M+H] ⁺ 182 N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.68-7.62 (m, 1H), 7.56 (s, 1H), 7.46 (d, J=8.7 Hz, 1H), 7. 28-7.21 (m, 1H), 7.18-7.07 (m, 3H), 6.82-6.75 (m, 2H), 6.63-6.56 (m, 2H), 6.49 (d, J=1.9 Hz, 1H), 4.03 (t, J=6.1 Hz, 2H), 3.01 (t, J=5.0 Hz, 4H), 2, 66-2.46 (m, 6H), 2.03-1.92 (m, 2H), 1.73 (s, 6H); 567 [M+H] ⁺ 183 N-(3-(5,6-dichloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.45 (br s, 1H), 7.75-7.65 (m, 2H), 7.53 (s, 1H), 7.43 (s, 1H), 6.96-6.87 (m, 3H), 4.52 (lat s, 1H), 4.06 (t, J=6.3 Hz, 2H), 2.97 (t, J =6.8 Hz, 2H), 2.90 (t, J=4.9 Hz, 4H), 2.68 (t, J=7.2 Hz, 2H), 2.55-2.37 (m , 6H), 2.05-1.96 (m, 2H), 1.85-1.75 (m, 2H); 526 [M+H] ⁺ 184 N-(3-(5,6-dichloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.54 (br s, 1H), 7.75-7.66 (m, 2H), 7.52 (s, 1H), 7.42 (s, 1H), 6.96-6.86 (m, 3H), 4.65 (t, J=6.3 Hz, 1H), 4.05 (t, J=6.3 Hz, 2H), 2, 96 (kv, J=6.6 Hz, 2H), 2.67 (t, J=7.3 Hz, 2H), 2.62-2.34 (m, 9H), 2.29 (s, 3H ), 2.07-1.93 (m, 3H), 1.79 (p, J=7.1 Hz, 2H); 540 [M+H] ⁺ 185 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyridin-4-yloxy)propyl)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.11 (br s, 1H), 7.75-7.70 (m, 2H), 7.40 (d, J=1.9 Hz, 1H) , 7.28-7.22 (m, 3H), 7.18-7.10 (m, 3H), 7.01 (d, J=2.2 Hz, 1H), 6.37-6.32 (m, 2H), 4.47 (t, J=5.8 Hz, 1H), 3.74 (t, J=7.1 Hz, 2H), 3.07 (kv, J=6.7 Hz , 2H), 2.71 (kv, J=7.5 Hz, 2H), 2.12 (p, J=14.8, 7.4 Hz, 2H), 1.81 (p, J=14, 2, 7.1 Hz, 2H); 489 [M+H] ⁺ 186 N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propyl)-benzenesulfonamide ^1H NMR (400 MHz, CDCl ₃ ) δ 8.62 (br s, 1H), 7.71 (d, J=8.3 Hz, 2H), 7.44 (d, J=1.9 Hz , 1H), 7.32-7.21 (m, 2H), 7.12 (dd, J=8.6, 2.0 Hz, 1H), 6.85 (d, J=1.8 Hz, 1H), 4.33 (t, J=6.2 Hz, 1H), 3.01 (kv, J=6.7 Hz, 2H), 2.70 (t, J=7.3 Hz, 4H) , 2.66-2.24 (m, 13H), 1.88-1.75 (m, 4H); 484 [M+H] ⁺ 187 N-((6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzene sulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.84-7.75 (m, 2H), 7.14 (dd, J=8.7, 4.4 Hz, 1H), 7.11-7.02 (m, 2H), 6.92 (dd, J=9.8, 2.5 Hz, 1H), 6.77-6.69 (m, 1H), 4.10 (t, J=6.1 Hz, 2H), 2.98-2.85 (m, 2H), 2.82-2.34 (m, 12H), 2.31 (s, 3H), 2.19-2.11 (m, 1H), 2.07-1.96 (m, 3H), 1.96-1.87 (m, 1H), 1.59-1.47 (m, 1H); 515 [M+H] ⁺ 188 N-((6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(piperazin-1-yl)propoxy)benzene sulfonamide ^1H NMR (400 MHz, MeOD) δ 7.83-7.76 (m, 2H), 7.14 (dd, J=8.7, 4.4 Hz, 1H), 7.10-7.04 (m, 2H), 6.92 (dd, J=9.8, 2.5 Hz, 1H), 6.77-6.68 (m, 1H), 4.11 (t, J=6.1 Hz, 2H), 2.97-2.84 (m, 6H), 2.78-2.63 (m, 3H), 2.63-2.43 (m, 6H), 2.20-2, 08 (m, 1H), 2.08-1.86 (m, 4H), 1.59-1.47 (m, 1H); 501 [M+H] ⁺ 189 4-(3-(4-methylpiperazin-1-yl)propoxy)-N-((2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)benzene sulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.83-7.76 (m, 2H), 7.29 (d, J=7.6 Hz, 1H), 7.20 (d, J=7.9 Hz, 1H), 7.09-7.03 (m, 2H), 7.01-6.95 (m, 1H), 6.95-6.89 (m, 1H), 4.14-4, 06 (m, 2H), 2.96-2.87 (m, 2H), 2.84-2.34 (m, 12H), 2.30 (s, 3H), 2.24-2.15 ( m, 1H), 2.08-1.86 (m, 5H), 160-1.48 (m, 1H); 497 [M+H] ⁺ 190 4-(3-(piperazin-1-yl)propoxy)-N-((2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)benzene sulfonamide ¹ H NMR (400 MHz, MeOD) δ 7.84-7.74 (m, 2H), 7.29 (d, J=7.7 Hz, 1H), 7.20 (d, J=7.9 Hz, 1H), 7.10-7.03 (m, 2H), 7.01-6.95 (m, 1H), 6.95-6.89 (m, 1H), 4.10 (t, J=6.1 Hz, 2H), 2.95-2.86 (m, 6H), 2.80-2.67 (m, 3H), 2.62-2.40 (m, 6H), 2 .24-2.15 (m, 1H), 2.07-1.88 (m, 4H), 1.59-1.49 (m, 1H); 484 [M+H] ⁺

<Analysis and Purification Conditions>

[LC-MS Analysis Conditions]

Device name: Shimadzu LCMS-2020

Column: ACE Excel2 C18, 75x2.1 mm

Mobile phase: acetonitrile/H ₂ O+0.1% TFA

Flow rate: 0.5ml/min

UV detector: 254 nm

[LCSD purification conditions]

Device name: CombiFlash®Rf+

UV detector: 254 nm

[Preparative HPLC Purification Conditions]

Device name: Gilson GX-281, pump 321, UV/VIS-155

Column: Luna® 10 νM C18 (2) 100 Å, 250×21.2 mm

Mobile phase: acetonitrile/0.1% TFA H ₂ O

Flow rate: 18ml/min

UV detector: 254 nm

[ ^1H NMR]

Device name: Bruker Avance (400 MHz)

<Experimental Example 1> Evaluation of Pin1 Enzyme Inhibitory Activity

To evaluate the Pin1 enzyme inhibitory activity of the compound of the present invention represented by Formula 1, the following experiment was conducted and the results are shown in Table 2 below.

The enzymatic activity of Pin1 protein was measured using the sensolyte Green Pin1 assay kit from Anaspec. The substrate was diluted in buffer at a ratio of 1:100 to obtain a concentration of 1 μM, and the protein was diluted in buffer at a ratio of 1:20 to prepare a concentration of 50 μg/ml. In addition, a developing solution was prepared by diluting it with buffer in a ratio of 1:100.

The compound obtained in each example was diluted with DMSO and prepared at a concentration of 100 μM, 10 μM, 1 μM or 0.1 μM using buffer. After sequentially adding 10 μl of the compound obtained in each example, diluted to four concentrations according to the above procedure, 10 μl of Pin1 protein and 30 μl of developing solution to each well of a black 96-well plate, 50 μl of substrate was finally added. Finally, 50 μL of substrate was added to each well of the plate and the enzymatic reaction was carried out after shaking the plate for 10 seconds.

The plate was then incubated for 2 hours at room temperature in a light-free environment, and fluorescence values were measured at 490 nm/520 nm using a Synergy Neo device (Tecan). The results are shown in Table 2 below by dividing the grades from A to D for each concentration (µM) at which Pin1 enzyme activity is inhibited.

[Table 2] Example Pin1 inhibition Example Pin1 inhibition Example Pin1 inhibition 1 D 65 C 128 B 2 D 66 A 129 B 3 D 67 B 130 A 4 D 68 B 131 B 5 D 69 B 132 B 6 D 70 A 133 A 7 D 71 C 134 A 8 D 72 C 135 B 9 D 73 C 136 B 10 D 74 B 137 A eleven C 75 A 138 A 12 C 76 B 139 B 13 D 77 A 140 A 14 D 78 B 141 A 15 D 79 A 142 B 16 D 80 B 143 A 17 D 81 B 144 B 18 D 82 B 145 A 19 D 83 A 146 A 20 C 84 B 147 A 21 C 85 C 148 A 22 C 86 A 149 A 23 D 87 A 150 A 24 D 88 A 151 A 25 D 89 C 152 A 26 C 90 A 153 A 27 C 91 A 154 A 28 D 92 A 155 B 29 D 93 A 156 B thirty D 94 B 157 B 31 B 95 B 158 A 32 D 96 B 159 A 33 D 97 B 160 A 34 C 98 A 161 A 35 C 99 A 162 B 36 B 100 A 163 B 37 D 101 A 164 A 38 D 102 A 165 A 39 D 103 A 166 A 40 D 104 A 167 A 41 D 105 A 168 A 42 D 106 A 169 A 43 C 107 A 170 A 44 D 108 A 171 A 45 B 109 A 172 A 46 D 110 B 173 A 47 D 111 B 174 A 48 C 112 A 175 A 49 C 113 A 176 A 50 C 114 A 177 A 51 D 115 A 178 A 52 C 116 A 179 B 53 C 117 A 180 B 54 C 118 A 181 B 55 C 119 B 182 B 56 A 120 B 183 A 57 C 121 A 184 A 58 B 122 B 185 A 59 B 123 A 186 A 60 B 124 A 187 A 61 A 125 A 188 A 62 B 126 B 189 A 63 B 127 A 190 A 64 C 128 B

* A<1 µM, 1 µM<B<10 µM, 10 µM<C<100 µM, 100 µM<D.

As shown in Table 2, it was confirmed that when treated with the compound of Example 56, 61, 66, 70, 75, 77, 79, 83, 86, 87, 88, 90, 91, 92, 93, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 112, 113, 114, 115, 116, 117, 118, 121, 123, 124, 125, 127, 130, 133, 134 , 137, 138, 140, 141, 143, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 158, 159, 160, 161, 164, 165, 166, 167, 168, 169 , 170, 171, 172, 173, 174, 175, 176, 177, 178, 183, 184, 185, 186, 187, 188, 189 or 190, the inhibitory activity of Pin1 was observed at concentrations less than 1 μM.

The above results show that the compounds of the examples of the present invention are excellent in inhibiting the Pin1 enzyme, and therefore it can be seen that the benzenesulfonamide derivative of the present invention can be effectively used as a pharmaceutical composition for the prevention or treatment of cancer.

<Experimental Example 2> Evaluation of the protein expression inhibitory ability of MDA-MB 231 triple negative breast cancer cell line

To confirm the ability of the compound represented by Formula 1 of the present invention to inhibit protein expression in the triple negative breast cancer cell line MDA-MB 231, the following experiment was performed and the results are shown in Table 3 below.

MDA-MB-231 cells were cultured in a 5% CO ₂ incubator at 37°C using RPMI medium supplemented with 10% FBS and 1% penicillin/streptomycin.

Cells were washed with PBS once daily and then replaced with new medium. Cells grown at a density of at least 90% were detached using trypsin/EDTA 1 day before the experiment and then seeded at a density of 100,000 per well in a 6-well plate.

On the next day of culture, the compound prepared in each example was treated at a concentration of 10 μM, and DMSO was treated at a concentration of 0.1% of the total as a control, followed by incubation for 72 hours. After 72 hours, the cells were washed twice with PBS, collected by scraping, and centrifuged at 13,000 rpm for 3 minutes to remove all supernatant, and only the cells were collected.

RIPA buffer (containing 1X protease inhibitor and phosphatase inhibitor) (80 μl/well) was added to the prepared cells and the plate was shaken every 5 minutes to disrupt the cells for 15 minutes. The disrupted cells were centrifuged at 13,000 rpm for 15 minutes to collect only the protein supernatant. The resulting protein was quantified using a protein quantitation kit (Pierece, MA, USA), and a total of 10 μg of protein was used for Western blotting.

The protein sample was isolated by 10% SDS-PAGE and transferred to a PVDF membrane. Anti-human cyclin D1 antibody (Cell signal) and anti-vinculin antibody were coupled to the protein sample, and protein expression was measured using ECL reagent and LAS4000 equipment. Measurements were quantified and summarized using ImageJ. The results are shown in Table 3 below by dividing the scores from A to D according to the amount of protein compared to the DMSO-treated control group.

[Table 3] Example MBA-MB-231 Example MBA-MB-231 Example MBA-MB-231 22 D 66 A 92 A 31 C 70 A 93 A 34 D 75 A 98 A 35 A 77 A 99 A 36 D 78 A 103 B 44 D 79 A 104 D 45 D 80 B 105 D 55 D 81 A 106 C 56 B 82 D 118 C 57 D 83 A 121 A 58 D 86 D 123 D 59 B 88 C 60 C 90 B 61 A 91 A

* 0<A<35%, 35%<B<50%, 50%<C<70%, 70%<D<100%.

As shown in Table 3, when treated with the compound of Example 35, 61, 66, 70, 75, 77, 78, 79, 81, 83, 91, 92, 93, 98, 99, or 121, the expression level of MDA protein was found to be increased -MB 231 triple negative breast cancer cell line is less than 35% compared to DMSO treated control group.

The above results show that the compounds of the examples of the present invention have excellent ability to inhibit the protein expression of MDA-MB 231 triple negative breast cancer cell line, and therefore it can be seen that the benzenesulfonamide derivative of the present invention can be effectively used as a pharmaceutical composition for the prevention or cancer treatment.

<Experimental Example 3> Viability assessment of MCF7, MCF7-SP, A2780 or A2780-SP cells

To confirm the inhibitory effect of the compound of the present invention represented by Formula 1 on the growth of MCF7, MCF7-SP, A2780 or A2780-SP cells, the following experiment was carried out, the results of which are presented in Tables 4 and 5 below.

MCF7 cells (breast cancer cells) were seeded in a 96-well plate at a density of 3000 viable cells per well and cultured in DMEM/high glucose supplemented with 10% FBS and 1% penicillin/streptomycin.

On the next day of culture, the cells were treated with the compound of Examples 71, 76, 80, 84, 92, 99, 100 or 119, followed by culture for 3 days. Cell viability was assessed using Cell-titer Glo (Promega, WC, USA), and luciferase activity was determined using a plate reader (Biocompare, USA).

On the other hand, MCF7-SP cells (breast cancer stem cells) were seeded in a round-bottom 96-well Ultra-Low Attachment plate (seeding) at a density of 1500 viable cells per well and cultured in cancer stem cell medium. Cancer stem cell media consists of neurobasal medium supplemented with 20 ng/mL bFGF, 10 ng/mL EGF, 2.5 ng/mL amphotericin B, HEPES, Glutamax, and B27.

On the next day of culture, the cells were treated with the compound of Example 71, 76, 80, 84, 92, 99, 100 or 119, followed by culture for 8 days. The medium containing the compound was added again on the 4th day. Sphere cell viability was assessed using Cell-titer Glo (Promega, WC, USA), and luciferase activity was determined using a Tecan plate reader (Biocompare, USA).

In addition, A2780 cells (ovarian cancer cells) were seeded in a 96-well plate at a density of 3000 viable cells per well and cultured in RPMI-1640 supplemented with 10% FBS and 1% penicillin/streptomycin.

On the next day of cultivation, the cells were treated with the compound of Examples 57 and 69-144, followed by cultivation for 3 days. Cell viability was assessed using Cell-titer Glo (Promega, WC, USA), and luciferase activity was determined using a Tecan plate reader (Biocompare, USA).

On the other hand, A2780-SP cells (ovarian cancer stem cells) were seeded in a round-bottom 96-well Ultra-Low Attachment plate (seeding) at a density of 1500 viable cells per well and cultured in cancer stem cell medium. Cancer stem cell media consists of neurobasal medium supplemented with 20 ng/mL bFGF, 10 ng/mL EGF, 2.5 ng/mL amphotericin B, HEPES, Glutamax, and B27.

On the next day of cultivation, the cells were treated with the compound of Examples 57 and 69-144, followed by cultivation for 8 days. The medium containing the compound was added there again on the 4th day. Sphere cell viability was assessed using Cell-titer Glo (Promega, WC, USA), and luciferase activity was determined using a Tecan plate reader (Biocompare, USA).

[Table 4] Example MCF7 MCF7-SP 70 B B 75 B C 79 C C 83 B B 91 B B 98 C C 99 B B 118 B B

* A<1 µM, 1 µM<B<10 µM, 10 µM<C.

[Table 5] Example A2780 A2780-SP Example A2780 A2780-SP Example A2780 A2780-SP 56 B A 114 - B 158 C A 59 B A 115 - A 159 C A 61 B A 117 - B 160 C C 66 B A 118 C A 161 C A 70 B A 121 B A 164 B A 75 B B 123 B B 165 B A 77 C B 124 B B 166 C B 79 C A 125 C B 167 B A 83 B A 127 C B 168 C A 88 C A 130 B B 169 B A 90 C A 133 C B 170 B A 91 C A 134 C A 171 C A 92 C A 137 C B 172 C A 93 B A 138 C B 173 B A 95 C B 140 - B 174 C A 98 B B 141 - B 175 B A 99 B A 143 - B 176 B A 100 B A 145 C C 177 B A 103 C A 146 C B 178 B A 104 C A 147 C C 183 C A 105 C A 148 C B 184 C A 106 B A 149 C C 185 C C 108 B A 150 C A 186 C A 109 B A 151 C A 187 C A 110 C A 152 C A 188 C A 111 C A 153 B A 189 C A 112 C A 154 B A 190 C A 113 - B 157 C A

* A<1 µM, 1 µM<B<10 µM, 10 µM<C, -: not studied.

As shown in Table 4, the concentration of MCF7 cells was less than 10 μM when treated with the compound of Example 70, 75, 83, 91, 99 or 118, and the concentration of MCF7-SP cells was less than 10 μM when treated with the compound of Examples 70, 83. 91, 99 or 118.

As shown in Table 5, the concentration of A2780 cells was less than 10 μM when treated with the compound of Example 56, 59, 61, 66, 70, 75, 83, 93, 98, 99, 100, 106, 108, 109, 121, 123 , 124, 130, 153, 154, 164, 165, 167, 169, 170, 173, 175, 176, 177 or 178, and the concentration was less than 1 μM when treated with the compound of Example 56, 59, 61, 66, 70 , 79, 83, 88, 90, 91, 92, 93, 99, 100, 103, 104, 105, 106, 108, 109, 110, 111, 112, 115, 118, 121, 134, 150, 151, 152 , 153, 154, 157, 158, 159, 161, 164, 165, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 183, 184, 186, 187, 1 88 , 189 or 190.

The above results show that the compounds of the examples of the present invention have excellent growth inhibitory effects on MCF7, MCF7-SP, A2780 or A2780-SP cells, and therefore it can be seen that the benzenesulfonamide derivative of the present invention can be effectively used as a pharmaceutical composition for the prevention or treatment of malignant neoplasms.

Claims (193)

1. The compound represented by Formula 1, or a pharmaceutically acceptable salt thereof: [Formula 1] , Where Ar is a 6-10 membered aryl or a 5-6 membered heteroaryl containing one or two heteroatoms selected from the group consisting of N, S and O; R ¹ and R ² independently represent hydrogen or halogen; R ³ represents a substituted straight or branched C _1-8 alkyl, NR ^a1 R ^a2 , OR ^a3 , or , where R ^a1 represents hydrogen, R ^a2 and R ^a3 independently represent substituted straight or branched C _1-8 alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted 5-6 membered heteroaryl containing one to three heteroatoms selected from the group , consisting of N, S and O, wherein the substituted alkyl is substituted with one substituent selected from the group consisting of unsubstituted or substituted 4-8 membered heterocycloalkyl containing one or two heteroatoms selected from the group consisting of N, S and O, and unsubstituted or substituted 4-6 membered heteroaryl containing one to three heteroatoms selected from the group consisting of N, S and O, and optionally further substituted with hydroxy, or forms a 3-6 membered cycloalkyl with a substituted carbon atom, wherein the substituted phenyl and the substituted 5-6 membered heteroaryl are independently substituted with one to three substituents selected from the group consisting of 4-8 membered unsubstituted or substituted heterocycloalkyl containing one or two heteroatoms selected from the group consisting of N, S and O, and halogen, and substituted 4-8 membered heterocycloalkyl is substituted with one to three substituents selected from the group consisting of straight or branched C _1-5 alkyl, unsubstituted or substituted with one or more halogen atoms, straight or branched C _1-5 alkylcarbonyl, NR ^b1 R ^b2 , halogen, hydroxy and oxo, and substituted 4-6 membered heteroaryl is substituted with one to three substituents selected from the group consisting of straight or branched C _1-5 alkyl and halogen, R ^b1 and R ^b2 independently represent hydrogen or straight or branched C _1-6 alkyl; L ¹ represents , where R ^c represents hydrogen; L ² represents straight or branched C _1-8 alkylene, unsubstituted or substituted by one hydroxy, or phenylene; Z is C _3-8 cycloalkyl fused with an unsubstituted or substituted 9-membered heteroaryl containing one or two heteroatoms representing N, a substituted 9-membered heteroaryl containing one or two heteroatoms representing N, or a substituted 9-membered heteroarylC _1-5 alkyl containing one or two heteroatoms representing N, where Z represents a substituted 9-membered heteroarylC _1-5 alkyl containing one or two heteroatoms representing N when L ² represents phenylene, wherein the substituted 9-membered heteroaryl in the substituted 9-membered heteroaryl and the substituted heteroarylC _1-5 alkyl is independently substituted with halogen, and optionally further substituted with straight or branched C _1-5 alkyl. 2. A compound, or a pharmaceutically acceptable salt thereof according to claim 1, where: Ar is a 6-10 membered aryl or a 5-6 membered heteroaryl containing one or two heteroatoms selected from the group consisting of N, S and O; R ¹ and R ² are independently hydrogen or fluorine; R ³ represents a substituted straight or branched C _1-6 alkyl, NR ^a1 R ^a2 , OR ^a3 , or , where R ^a1 represents hydrogen, R ^a2 and R ^a3 independently represent substituted straight or branched C _1-6 alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted 5-6 membered heteroaryl containing one or two heteroatoms selected from the group, consisting of N, S and O, wherein the substituted alkyl is substituted with one substituent selected from the group consisting of unsubstituted or substituted 4-7 membered heterocycloalkyl containing one or two heteroatoms selected from the group consisting of N, S and O, and unsubstituted or substituted 4-6 membered heteroaryl containing one to three heteroatoms selected from the group consisting of N, S and O, and is additionally substituted with hydroxy, or forms a 3-5 membered cycloalkyl with a substituted carbon atom, wherein the substituted phenyl and the substituted 5-6 membered heteroaryl are independently substituted with one to three substituents selected from the group consisting of 4-7 membered unsubstituted or substituted heterocycloalkyl containing one or two heteroatoms selected from the group consisting of N, S and O, and halogen, and substituted 4-7 membered heterocycloalkyl is independently substituted with one to three substituents selected from the group consisting of straight or branched C _1-4 alkyl, unsubstituted or substituted with one or more halogens, straight or branched C _1-4 alkylcarbonyl, NR ^b1 R ^b2 , chlorine, fluorine, bromine, hydroxy and oxo, and substituted 4-6 membered heteroaryl is substituted with one to three substituents selected from the group consisting of straight or branched C _1-4 alkyl, chlorine, fluorine and bromine, R ^b1 and R ^b2 independently represent hydrogen or straight or branched C _1-3 alkyl; L ¹ represents , where R ^c represents hydrogen; L ² represents straight or branched C _1-6 alkylene, unsubstituted or substituted with one substituent selected from hydroxy and phenylene; Z is C _4-7 cycloalkyl fused with an unsubstituted or substituted 9-membered heteroaryl containing one or two heteroatoms representing N, a substituted 9-membered heteroaryl containing one or two heteroatoms representing N, or a substituted 9-membered heteroarylC _1-4 alkyl containing one or two heteroatoms representing N, where Z represents a substituted 9-membered heteroarylC _1-4 alkyl containing one or two heteroatoms representing N when L ² represents phenylene, wherein the substituted 9-membered heteroaryl in the substituted 9-membered heteroaryl and the substituted heteroarylC _1-4 alkyl is independently substituted with one or more substituents selected from the group consisting of fluorine, chlorine, and bromine, and is optionally further substituted with straight or branched C _1-4 alkyl. 3. A compound, or a pharmaceutically acceptable salt thereof according to claim 1, where: Ar is phenyl, naphthyl, pyridyl or thiazolyl; R ¹ and R ² are independently hydrogen or fluorine; R ³ represents a substituted straight or branched C _1-5 alkyl, NR ^a1 R ^a2 , OR ^a3 , or , where R ^a1 represents hydroxy, R ^a2 and R ^a3 independently represent substituted straight or branched C _1-5 alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted 5-6 membered heteroaryl containing one to three heteroatoms selected from the group, consisting of N, S and O, wherein the substituted alkyl is substituted by one or more substituents selected from the group consisting of unsubstituted or substituted 4-7 membered heterocycloalkyl containing one or two heteroatoms selected from the group consisting of N, S and O, and unsubstituted or substituted 5-6 -membered heteroaryl containing one to three heteroatoms selected from the group consisting of N, S and O, or optionally further substituted with hydroxy, or forms a cyclopropyl with a substituted carbon atom, wherein the substituted phenyl and the substituted 5-6 membered heteroaryl are independently substituted with one or more substituents selected from the group consisting of unsubstituted or substituted 4-7 membered heterocycloalkyl containing one or two heteroatoms selected from the group consisting of N, S and O, unsubstituted or substituted 5-6 membered heteroaryl containing one to three heteroatoms selected from the group consisting of N, S and O, NR ^b1 R ^b2 , 3-4 membered cycloalkyl, halogen, hydroxy and sulfonyl, and substituted 4-7 membered heterocycloalkyl is substituted with one to three substituents selected from the group consisting of straight or branched C _1-3 alkyl, unsubstituted or substituted with one or more fluorine atoms, straight or branched C _1-4 alkylcarbonyl, NR ^b1 R ^b2 , chlorine, fluorine, bromine, hydroxy and oxo, and substituted 5-6-membered heteroaryl is substituted with one to three substituents selected from the group consisting of straight or branched C _1-3 alkyl, chlorine, fluorine and bromine, R ^b1 and R ^b2 are independently hydrogen, methyl or ethyl; L ¹ represents , where R ^c represents hydrogen; L ² represents straight or branched C _1-4 alkylene, unsubstituted or substituted hydroxy, or phenylene; Z is a C _5-6 cycloalkyl fused to an unsubstituted 9-membered heteroaryl containing one or two heteroatoms representing N, a substituted 9-membered heteroaryl containing one or two heteroatoms representing N, or a 9-membered heteroaryl C _{1- 3} alkyl containing one or two heteroatoms representing N, where Z represents a 9-membered heteroarylC _1-4 alkyl containing one or two heteroatoms representing N when L ² represents phenylene, wherein the substituted 9-membered heteroaryl in the substituted 9-membered heteroaryl and the substituted 9-membered heteroarylC _1-3 alkyl are independently substituted with one to three substituents selected from the group consisting of fluorine, chlorine and bromine, and optionally further substituted with straight or branched C _{1 -3} alkyl. 4. A compound, or a pharmaceutically acceptable salt thereof according to claim 1, where: Ar is phenyl, naphthyl, pyridine or thiazole; R ¹ and R ² are independently hydrogen or fluorine; R ³ represents , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , or ; L ¹ represents ; L ² represents , , , , or ; Z represents , , , , , , , , , , , or . 5. A compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of the following compounds: <56> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <59> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzenesulfonamide; <61> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <63> 4-(3-(4-ethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl)benzenesulfonamide; <66> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <70> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <71> 5-fluoro-3-(1-((4-(3-(4-methylpiperazin-1-yl)propoxy)phenyl)sulfonyl)piperidin-4-yl)-1H-indole; <72> 4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)-N-(3-(5-fluoro-1H-indol-3-yl)propyl)benzenesulfonamide; <73> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-isobutyrylpiperazin-1-yl)propoxy)benzenesulfonamide; <74> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)propoxy)benzenesulfonamide ; <75> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-hydroxypiperidin-1-yl)propoxy)benzenesulfonamide; <76> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)propoxy)benzenesulfonamide ; <77> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-(methylamino)azetidin-1-yl)propoxy)benzenesulfonamide; <78> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-chloropiperidin-1-yl)propoxy)benzenesulfonamide; <79> N-(3-(5-chloro-1H-indol-3-yl)propyl)-6-(3-(piperazin-1-yl)propoxy)pyridin-3-sulfonamide; <80> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-fluoropiperidin-1-yl)propoxy)benzenesulfonamide; <81> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-(trifluoromethyl)piperidin-1-yl)propoxy)benzenesulfonamide; <82> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,4-difluoropiperidin-1-yl)propoxy)benzenesulfonamide; <83> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-1,4-diazepan-1-yl)propoxy)benzenesulfonamide; <84> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzenesulfonamide; <86> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)naphthalene-1-sulfonamide; <87> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)propoxy)benzenesulfonamide; <88> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-4-yl)propyl)amino)benzenesulfonamide; <90> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-1-yl)butyl)benzenesulfonamide; <91> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperazin-1-yl)butyl)benzenesulfonamide; <92> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(1-methylpiperidin-4-yl)propoxy)benzenesulfonamide; <93> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-4-yl)propoxy)benzenesulfonamide; <94> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperidin-4-yl)propoxy)benzenesulfonamide; <95> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperidin-1-yl)propoxy)benzenesulfonamide; <96> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <97> N-(3-(5-fluoro-1H-indol-3-yl)propyl)-4-(3-(piperidin-4-yl)propoxy)benzenesulfonamide; <98> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methylpiperazin-1-yl)propyl)amino)benzenesulfonamide; <99> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(piperidin-4-yl)butyl)benzenesulfonamide; <100> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyrrolidin-1-yl)propoxy)benzenesulfonamide; <101> 4-(3-(azepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <102> 4-(3-(1,4-diazepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <103> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <104> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <105> N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluoro-4-(3-(4-hydroxypiperidin-1-yl)propoxy)benzenesulfonamide; <106> 4-(3-(1,4-diazepan-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-3-fluorobenzenesulfonamide; <107> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <108> (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <109> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <110> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propoxy)benzenesulfonamide; <111> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3,4-dimethylpiperazin-1-yl)propoxy)benzenesulfonamide; <112> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(4-methylpiperazin-1-yl)butyl)benzenesulfonamide; <113> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperazin-1-yl)propyl)amino)benzenesulfonamide; <114> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperidin-1-yl)propyl)amino)benzenesulfonamide; <115> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(4-(1-methylpiperidin-4-yl)butyl)benzenesulfonamide; <116> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-((4-methylpiperazin-1-yl)methyl)cyclopropyl)methoxy)benzenesulfonamide; <117> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((1-(piperazin-1-ylmethyl)cyclopropyl)methoxy)benzenesulfonamide; <118> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)phenoxy)benzenesulfonamide; <119> 4-(3-bromophenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <120> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperidin-1-yl)phenoxy)benzenesulfonamide; <121> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)phenoxy)benzenesulfonamide; <122> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-1,4-diazepan-1-yl)phenoxy)benzenesulfonamide; <123> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-methylpiperazin-1-yl)phenyl)amino)benzenesulfonamide; <124> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(piperazin-1-yl)phenyl)amino)benzenesulfonamide; <125> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)pyrimidin-2-yl)amino)benzenesulfonamide; <126> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-morpholinophenyl)amino)benzenesulfonamide; <127> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(piperazin-1-yl)pyrimidin-2-yl)amino)benzenesulfonamide; <128> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-morpholinophenoxy)benzenesulfonamide; <129> 4-(3-(1,4-diazepan-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <130> 4-(3,5-bis(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <131> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide; <132> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-(piperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide; <133> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide; <134> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(piperazin-1-yl)pyridin-2-yl)amino)benzenesulfonamide; <135> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyrrolidin-1-yl)phenoxy)benzenesulfonamide; <136> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-hydroxypiperidin-1-yl)phenoxy)benzenesulfonamide; <137> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-fluoro-5-(4-methylpiperazin-1-yl)phenoxy)benzenesulfonamide; <138> 4-(3-bromo-5-(4-methylpiperazin-1-yl)phenoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <139> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((3-(4-hydroxypiperidin-1-yl)phenyl)amino)benzenesulfonamide; <140> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((6-chloro-4-(4-methylpiperazin-1-yl)pyridin-2-yl)amino )benzenesulfonamide; <141> 4-((4,6-bis(4-methylpiperazin-1-yl)pyridin-2-yl)amino)-N-(3-(5-chloro-1H-indol-3-yl)propyl) benzenesulfonamide; <142> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-((4-(4-methylpiperazin-1-yl)phenyl)amino)benzenesulfonamide; <145> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(methylsulfonyl)propoxy)benzenesulfonamide; <146> N-(3-(5-chloro-1H-indol-3-yl)propyl)-2-((3-(piperazin-1-yl)propyl)amino)thiazol-5-sulfonamide; <147> N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <148> 4-(4-(1H-imidazol-1-yl)butyl)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <149> N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <150> N-(2-((5-chloro-1H-indol-3-yl)methyl)phenyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <151> N-(4-(5-chloro-1H-indol-3-yl)butan-2-yl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <152> N-(4-(5-chloro-1H-indol-3-yl)butan-2-yl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <153> N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <154> N-(3-(5-bromo-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <157> N-(3-(5-chloro-2-methyl-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <158> N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <159> N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <160> 4-(3-(1H-1,2,4-triazol-1-yl)propoxy)-N-(3-(5-chloro-1H-indol-3-yl)propyl)benzenesulfonamide; <161> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(2-methyl-1H-imidazol-1-yl)propoxy)benzenesulfonamide; <162> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methyl-3-oxopiperazin-1-yl)propoxy)benzenesulfonamide; <163> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(3-oxopiperazin-1-yl)propoxy)benzenesulfonamide; <164> N-(3-(5,7-dichloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <165> N-(3-(5,7-dichloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <166> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,5-dichloro-1H-imidazol-1-yl)propoxy)benzenesulfonamide; <167> N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <168> N-(3-(5-chloro-1H-indazol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <169> N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <170> N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <171> (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <172> (R)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(piperazin-1-yl)propoxy)benzenesulfonamide; <173> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <174> (S)-N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(2-hydroxy-3-(piperazin-1-yl)propoxy)benzenesulfonamide; <175> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4,5-dimethyl-1H-imidazol-1-yl)propoxy)benzenesulfonamide; <176> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(2,4,5-trimethyl-1H-imidazol-1-yl)propoxy)benzenesulfonamide; <177> N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <178> N-((6-chloro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <179> N-(3-(5-chloro-1H-indol-3-yl)cyclohexyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <180> N-(3-(5-chloro-1H-indol-3-yl)cyclohexyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <181> N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide ; <182> N-(2-(2-(5-chloro-1H-indol-3-yl)propan-2-yl)phenyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <183> N-(3-(5,6-dichloro-1H-indol-3-yl)propyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <184> N-(3-(5,6-dichloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <185> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(pyridin-4-yloxy)propyl)benzenesulfonamide; <186> N-(3-(5-chloro-1H-indol-3-yl)propyl)-4-(3-(4-methylpiperazin-1-yl)propyl)benzenesulfonamide; <187> N-((6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(4-methylpiperazin-1-yl)propoxy)benzenesulfonamide; <188> N-((6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)-4-(3-(piperazin-1-yl)propoxy)benzenesulfonamide; <189> 4-(3-(4-methylpiperazin-1-yl)propoxy)-N-((2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)benzenesulfonamide; <190> 4-(3-(piperazin-1-yl)propoxy)-N-((2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl)benzenesulfonamide. 6. A method for producing a compound represented by Formula 1, comprising the step of producing a compound represented by Formula 1 by reacting a compound represented by Formula 2 with a compound represented by Formula 3, as shown in Reaction Scheme 1 below: [Reaction Scheme 1] where in reaction 1 Ar, R ¹ , R ² , R ³ , L ¹ , L ² and Z have the values defined in formula 1 according to claim 1, J ¹ is chlorosulfone; And J ² represents an amine. 7. A pharmaceutical composition containing the compound, or a pharmaceutically acceptable salt thereof according to claim 1, as an active ingredient for the prevention or treatment of malignancy. 8. The pharmaceutical composition according to claim 7, wherein the compound inhibits Pin1 (peptidyl-prolyl cis-trans isomerase interacting with 1). 9. The pharmaceutical composition according to claim 7, wherein the malignancy is at least one selected from the group consisting of intrahepatic cholangiocarcinoma, hepatoblastoma, liver cancer, thyroid cancer, colon cancer, testicular cancer, myelodysplastic syndrome, glioblastoma, oral cancer, lip cancer, mycosis fungoides, acute myelogenous leukemia, acute lymphocytic leukemia, basal cell carcinoma, epithelial ovarian carcinoma, ovarian germ cell carcinoma, male breast cancer, brain cancer, pituitary adenoma, multiple myeloma, gallbladder cancer, cancer biliary tract, colorectal cancer, chronic myelogenous leukemia, chronic lymphocytic leukemia, retinoblastoma, choroidal melanoma, Vater ampullary cancer, bladder cancer, peritoneal cancer, parathyroid cancer, adrenal cancer, nasal cavity cancer, non-small cell lung cancer, tongue cancer, astrocytoma, small cell lung cancer, pediatric brain cancer, pediatric lymphoma, childhood leukemia, small bowel cancer, meningioma, esophageal cancer, glioma, kidney cancer, renal cancer, heart cancer, duodenal cancer, malignant soft tissue cancer, malignant bone cancer, malignant lymphoma, malignant mesothelioma, malignant melanoma, eye cancer, vulvar cancer, urethral cancer, cancer of unknown primary site, gastric lymphoma, stomach cancer, gastric cancer, interstitial cancer of the gastrointestinal tract, Wilms cancer, breast cancer, sarcoma, penile cancer, pharyngeal cancer , pregnancy villous disease, cervical cancer, endometrial cancer, uterine sarcoma, prostate cancer, metastatic bone cancer, metastatic brain cancer, mediastinal cancer, rectal cancer, rectal carcinoid tumor, vaginal cancer, spinal cord cancer, vestibular schwannoma, pancreatic cancer, salivary gland cancer, Kaposi's sarcoma, Paget's disease, tonsil cancer, squamous cell carcinoma, lung adenocarcinoma, lung cancer, squamous cell lung cancer, skin cancer, anal cancer, rhabdomyosarcoma, laryngeal cancer, pleural cancer, blood cancer and thymus cancer. 10. A pharmaceutical composition containing the compound, or a pharmaceutically acceptable salt thereof, according to claim 1 as an active ingredient, for the prevention or treatment of conditions associated with inhibition of Pin1 (peptidyl-prolyl cis-trans isomerase interacting 1). 11. A method of preventing or treating cancer, comprising administering to a subject in need thereof a compound according to claim 1 or a pharmaceutically acceptable salt thereof. 12. The method according to claim 11, where the compound inhibits Pin1 (peptidyl-prolyl cis-trans isomerase interacting with 1). 13. The method of claim 11, wherein the malignancy is at least one selected from the group consisting of pseudomyxoma, intrahepatic cholangiocarcinoma, hepatoblastoma, liver cancer, thyroid cancer, colon cancer, testicular cancer, myelodysplastic syndrome, glioblastoma, cancer oral cavity, lip cancer, mycosis fungoides, acute myelogenous leukemia, acute lymphocytic leukemia, basal cell carcinoma, epithelial ovarian carcinoma, ovarian germ cell carcinoma, male breast cancer, brain cancer, pituitary adenoma, multiple myeloma, gallbladder cancer, bile duct cancer pathways, colorectal cancer, chronic myelogenous leukemia, chronic lymphocytic leukemia, retinoblastoma, choroidal melanoma, Vater ampullary cancer, bladder cancer, peritoneal cancer, parathyroid cancer, adrenal cancer, nasal cavity cancer, non-small cell lung cancer, tongue cancer, astrocytoma, small cell cancer lung, pediatric brain cancer, pediatric lymphoma, childhood leukemia, small bowel cancer, meningioma, esophageal cancer, glioma, kidney cancer, kidney cancer, heart cancer, duodenal cancer, malignant soft tissue cancer, malignant bone cancer, malignant lymphoma, malignant mesothelioma , malignant melanoma, eye cancer, vulvar cancer, urethral cancer, cancer of unknown primary site, gastric lymphoma, stomach cancer, stomach cancer, interstitial cancer of the gastrointestinal tract, Wilms cancer, breast cancer, sarcoma, penile cancer, pharyngeal cancer, pregnancy villous disease, cervical cancer, endometrial cancer, uterine sarcoma, prostate cancer, metastatic bone cancer, metastatic brain cancer, mediastinal cancer, rectal cancer, rectal carcinoid tumor, vaginal cancer, spinal cord cancer, vestibular schwannoma, cancer pancreas, salivary gland cancer, Kaposi's sarcoma, Paget's disease, tonsil cancer, squamous cell carcinoma, lung adenocarcinoma, lung cancer, squamous cell lung cancer, skin cancer, anal cancer, rhabdomyosarcoma, laryngeal cancer, pleural cancer, blood cancer and thymus cancer. 14. A method of preventing or treating conditions associated with Pin1 (peptidyl-prolyl cis-trans isomerase interacting 1) inhibition, comprising administering to a subject in need thereof a compound of claim 1 or a pharmaceutically acceptable salt thereof. 15. Use of a compound according to claim 1 or a pharmaceutically acceptable salt thereof for the production of a medicinal product for the prevention or treatment of malignancy. 16. Use of a compound according to claim 15, wherein the compound inhibits Pin1 (peptidyl-prolyl cis-trans isomerase interacting with 1). 17. Use of a compound according to claim 15, wherein the malignancy is at least one selected from the group consisting of pseudomyxoma, intrahepatic cholangiocarcinoma, hepatoblastoma, liver cancer, thyroid cancer, colon cancer, testicular cancer, myelodysplastic syndrome, glioblastoma, oral cancer, lip cancer, mycosis fungoides, acute myelogenous leukemia, acute lymphocytic leukemia, basal cell carcinoma, epithelial ovarian carcinoma, ovarian germ cell carcinoma, male breast cancer, brain cancer, pituitary adenoma, multiple myeloma, gallbladder cancer , biliary tract cancer, colorectal cancer, chronic myelogenous leukemia, chronic lymphocytic leukemia, retinoblastoma, choroidal melanoma, Vater ampullary cancer, bladder cancer, peritoneal cancer, parathyroid cancer, adrenal cancer, nasal cavity cancer, non-small cell lung cancer, tongue cancer, astrocytoma , small cell lung cancer, pediatric brain cancer, pediatric lymphoma, childhood leukemia, small bowel cancer, meningioma, esophageal cancer, glioma, kidney cancer, kidney cancer, heart cancer, duodenal cancer, malignant soft tissue cancer, malignant bone cancer, malignant lymphoma , malignant mesothelioma, malignant melanoma, eye cancer, vulvar cancer, urethral cancer, cancer of unknown primary site, gastric lymphoma, stomach cancer, stomach cancer, interstitial cancer of the gastrointestinal tract, Wilms cancer, breast cancer, sarcoma, penile cancer, pharyngeal cancer, villous disease of pregnancy, cervical cancer, endometrial cancer, uterine sarcoma, prostate cancer, metastatic bone cancer, metastatic brain cancer, mediastinal cancer, rectal cancer, rectal carcinoid tumor, vaginal cancer, spinal cord cancer, vestibular schwannoma, pancreatic cancer, salivary gland cancer, Kaposi's sarcoma, Paget's disease, tonsil cancer, squamous cell cancer, lung adenocarcinoma, lung cancer, squamous cell lung cancer, skin cancer, anal cancer, rhabdomyosarcoma, laryngeal cancer, pleural cancer, blood cancer and cancer thymus. 18. Use of a compound according to claim 1 or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for the prevention or treatment of conditions associated with inhibition of Pin1 (peptidyl-prolyl cis-trans isomerase interacting 1).