NO313331B1 - O6-alkylguaninderivater, fremgangsmåte for fremstilling og anvendelse derav samt farmasöytiske preparater - Google Patents

O6-alkylguaninderivater, fremgangsmåte for fremstilling og anvendelse derav samt farmasöytiske preparater Download PDF

Info

Publication number: NO313331B1
Authority: NO; Norway
Prior art keywords: guanine; cells; compound according; atase; ring
Prior art date: 1993-06-08

Application number

NO19954985A

Other languages

English (en)

Norwegian (no)

Other versions

NO954985L (no

NO954985D0 (no

Inventor

Thomas Brian Hamilton Mcmurry

Robert Stanley Mcelhinney

Joan Elizabeth Mccormick

Rhoderick Hugh Elder

Jane Kelly

Geoffrey Paul Margison

Joseph Anthony Raffery

Amanda Jean Watson

Mark Andrew Willington

Original Assignee

Cancer Res Campaign Tech

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-06-08

Filing date

1995-12-07

Publication date

2002-09-16

1994-05-23 Priority claimed from GB9410421A external-priority patent/GB9410421D0/en

1995-12-07 Application filed by Cancer Res Campaign Tech filed Critical Cancer Res Campaign Tech

1995-12-07 Publication of NO954985D0 publication Critical patent/NO954985D0/no

1996-02-07 Publication of NO954985L publication Critical patent/NO954985L/no

2002-09-16 Publication of NO313331B1 publication Critical patent/NO313331B1/no

Links

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XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 1
229960003901 dacarbazine Drugs 0.000 description 1
230000009615 deamination Effects 0.000 description 1
238000006481 deamination reaction Methods 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
238000007865 diluting Methods 0.000 description 1
PVRATXCXJDHJJN-UHFFFAOYSA-N dimethyl 2,3-dihydroxybutanedioate Chemical compound COC(=O)C(O)C(O)C(=O)OC PVRATXCXJDHJJN-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
230000002900 effect on cell Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
JJTJZFLRKYYGGS-UHFFFAOYSA-N ethoxyethane;methylsulfinylmethane Chemical compound CS(C)=O.CCOCC JJTJZFLRKYYGGS-UHFFFAOYSA-N 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229960004783 fotemustine Drugs 0.000 description 1
YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
108010052968 leupeptin Proteins 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
238000006138 lithiation reaction Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
JGJDORZNOSWWDS-UHFFFAOYSA-N methyl 1,3-oxazole-5-carboxylate Chemical compound COC(=O)C1=CN=CO1 JGJDORZNOSWWDS-UHFFFAOYSA-N 0.000 description 1
GCVVHNKBMLQFCY-UHFFFAOYSA-N methyl 5-(hydroxymethyl)furan-2-carboxylate Chemical compound COC(=O)C1=CC=C(CO)O1 GCVVHNKBMLQFCY-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
231100000324 minimal toxicity Toxicity 0.000 description 1
QXYYYPFGTSJXNS-UHFFFAOYSA-N mitozolomide Chemical compound N1=NN(CCCl)C(=O)N2C1=C(C(=O)N)N=C2 QXYYYPFGTSJXNS-UHFFFAOYSA-N 0.000 description 1
229950005967 mitozolomide Drugs 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
231100000243 mutagenic effect Toxicity 0.000 description 1
230000003505 mutagenic effect Effects 0.000 description 1
230000003039 myelosuppressive effect Effects 0.000 description 1
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical class NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
230000002018 overexpression Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
231100000683 possible toxicity Toxicity 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
229960000624 procarbazine Drugs 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
201000003708 skin melanoma Diseases 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000011272 standard treatment Methods 0.000 description 1
210000000130 stem cell Anatomy 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000004114 suspension culture Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000009210 therapy by ultrasound Methods 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19954985A 1993-06-08 1995-12-07 O6-alkylguaninderivater, fremgangsmåte for fremstilling og anvendelse derav samt farmasöytiske preparater NO313331B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IE930432		1993-06-08
GB9410421A GB9410421D0 (en)	1993-06-08	1994-05-23	O (six)-substituted guanine derivatives
PCT/IE1994/000031 WO1994029312A1 (en)	1993-06-08	1994-06-08	O6-substituted guanine derivatives, a process for their preparation and their use in treating tumour cells

Publications (3)

Publication Number	Publication Date
NO954985D0 NO954985D0 (no)	1995-12-07
NO954985L NO954985L (no)	1996-02-07
NO313331B1 true NO313331B1 (no)	2002-09-16

Family

ID=26304937

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19954985A NO313331B1 (no)	1993-06-08	1995-12-07	O6-alkylguaninderivater, fremgangsmåte for fremstilling og anvendelse derav samt farmasöytiske preparater

Country Status (19)

Country	Link
EP (1)	EP0702683B8 (de)
JP (1)	JP4054057B2 (de)
CN (1)	CN1048493C (de)
AT (1)	ATE250060T1 (de)
AU (1)	AU697977B2 (de)
CA (1)	CA2164847C (de)
CZ (1)	CZ290951B6 (de)
DE (1)	DE69433161T2 (de)
DK (1)	DK0702683T3 (de)
ES (1)	ES2207638T3 (de)
FI (1)	FI955906A7 (de)
HU (1)	HU217779B (de)
NO (1)	NO313331B1 (de)
NZ (1)	NZ266527A (de)
PL (1)	PL180681B1 (de)
PT (1)	PT702683E (de)
RU (1)	RU2154646C2 (de)
SK (1)	SK282621B6 (de)
WO (1)	WO1994029312A1 (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6043228A (en) *	1993-06-08	2000-03-28	Cancer Research Campaign Technology Limited	O6 -substituted guanine derivatives, a process for their preparation and their use in treating tumor cells
US5929046A (en) *	1994-06-08	1999-07-27	Cancer Research Campaign Technology Limited	Pyrimidine and purine derivatives and their use in treating tumour cells
US5525606A (en)	1994-08-01	1996-06-11	The United States Of America As Represented By The Department Of Health And Human Services	Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines
DE19618727C2 (de) *	1996-05-09	2000-02-17	Deutsches Krebsforsch	Herstellung alkylierter Nucleosid-3'-Phosphate
AU6771198A (en) *	1997-03-24	1998-10-20	Glaxo Group Limited	Method for treating b-cell tumors with ara-g nucleoside derivatives
EP1017394B1 (de) *	1997-07-12	2005-12-07	Cancer Research Technology Limited	Cyclin-abhängige-kinase inhibierende purinderivate
US6060458A (en) *	1998-02-13	2000-05-09	The United States Of America As Represented By The Department Of Health And Human Services	Oligodeoxyribonucleotides comprising O6 -benzylguanine and their use
DE60212642T2 (de) *	2001-04-10	2007-06-14	ECOLE POLYTECHNIQUE FéDéRALE DE LAUSANNE	Verfahren zur verwendung von o6-alkylguanin-dna-alkyltransferasen
WO2003090686A2 (en)	2002-04-25	2003-11-06	University Of Connecticut Health Center	Using heat shock proteins to improve the therapeutic benefit of a non-vaccine treatment modality
US6984389B2 (en) *	2002-04-25	2006-01-10	University Of Connecticut Health Center	Using heat shock proteins to improve the therapeutic benefit of a non-vaccine treatment modality
US20080039321A1 (en) *	2004-05-12	2008-02-14	Bastiaans Henricus M	Plant Growth Regulation
CN100350975C (zh) *	2005-02-03	2007-11-28	山东蓝金生物工程有限公司	抗癌药物组合物
GB0502573D0 (en) *	2005-02-08	2005-03-16	Topotarget As	Therapeutic compounds
GB0907551D0 (en)	2009-05-01	2009-06-10	Univ Dundee	Treatment or prophylaxis of proliferative conditions
CN104031048B (zh) *	2014-05-28	2016-03-09	北京工业大学	一种β-氯乙基亚硝基脲类化合物及其合成方法和用途
CN104031047B (zh) *	2014-05-28	2016-03-09	北京工业大学	一种具有抗癌活性的氯乙基亚硝基脲及其合成方法
CN107098906B (zh) *	2017-05-19	2020-05-05	四川大学	苄基鸟嘌呤衍生物及其有机盐类化合物和药物组合物及其应用
AU2019216531A1 (en)	2018-02-02	2020-09-24	Maverix Oncology, Inc.	Small molecule drug conjugates of gemcitabine monophosphate

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2139107A1 (de) *	1971-08-04	1973-02-15	Merck Patent Gmbh	Heterocyclisch substituierte adenosinverbindungen
AP160A (en) *	1987-08-15	1991-11-18	The Wellcome Foundation Ltd	Therapeutic acyclic nucleosides.
US5352669A (en) *	1990-03-13	1994-10-04	The Of The United States Of America As Represented By The Department Of Health And Human Services	O6 -benzylated guanine, guanosine and 2'-deoxyguanosine compounds possessing O6 -alkylguanine-DNA alkyltransferase depleting activity

1994
- 1994-06-08 HU HU9503522A patent/HU217779B/hu not_active IP Right Cessation
- 1994-06-08 WO PCT/IE1994/000031 patent/WO1994029312A1/en not_active Ceased
- 1994-06-08 RU RU96102153/04A patent/RU2154646C2/ru not_active IP Right Cessation
- 1994-06-08 CN CN94193024A patent/CN1048493C/zh not_active Expired - Fee Related
- 1994-06-08 JP JP50154395A patent/JP4054057B2/ja not_active Expired - Fee Related
- 1994-06-08 AT AT94916373T patent/ATE250060T1/de not_active IP Right Cessation
- 1994-06-08 ES ES94916373T patent/ES2207638T3/es not_active Expired - Lifetime
- 1994-06-08 PT PT94916373T patent/PT702683E/pt unknown
- 1994-06-08 CA CA002164847A patent/CA2164847C/en not_active Expired - Fee Related
- 1994-06-08 DK DK94916373T patent/DK0702683T3/da active
- 1994-06-08 DE DE69433161T patent/DE69433161T2/de not_active Expired - Fee Related
- 1994-06-08 CZ CZ19953233A patent/CZ290951B6/cs not_active IP Right Cessation
- 1994-06-08 AU AU68059/94A patent/AU697977B2/en not_active Ceased
- 1994-06-08 PL PL94311950A patent/PL180681B1/pl not_active IP Right Cessation
- 1994-06-08 SK SK1547-95A patent/SK282621B6/sk unknown
- 1994-06-08 EP EP94916373A patent/EP0702683B8/de not_active Expired - Lifetime
- 1994-06-08 NZ NZ266527A patent/NZ266527A/en not_active IP Right Cessation
1995
- 1995-12-07 NO NO19954985A patent/NO313331B1/no unknown
- 1995-12-08 FI FI955906A patent/FI955906A7/fi unknown

Also Published As

Publication number	Publication date
AU697977B2 (en)	1998-10-22
JPH08511773A (ja)	1996-12-10
CN1145622A (zh)	1997-03-19
RU2154646C2 (ru)	2000-08-20
FI955906A0 (fi)	1995-12-08
CA2164847A1 (en)	1994-12-22
WO1994029312A1 (en)	1994-12-22
FI955906A7 (fi)	1996-02-02
CZ323395A3 (en)	1996-06-12
PL180681B1 (pl)	2001-03-30
ES2207638T3 (es)	2004-06-01
SK282621B6 (sk)	2002-10-08
ATE250060T1 (de)	2003-10-15
HU217779B (hu)	2000-04-28
NO954985L (no)	1996-02-07
AU6805994A (en)	1995-01-03
JP4054057B2 (ja)	2008-02-27
EP0702683A1 (de)	1996-03-27
DK0702683T3 (da)	2004-02-02
DE69433161D1 (de)	2003-10-23
NZ266527A (en)	1999-10-28
NO954985D0 (no)	1995-12-07
CN1048493C (zh)	2000-01-19
HUT74574A (en)	1997-01-28
HU9503522D0 (en)	1996-02-28
PT702683E (pt)	2004-01-30
CZ290951B6 (cs)	2002-11-13
DE69433161T2 (de)	2004-07-08
EP0702683B8 (de)	2004-09-08
PL311950A1 (en)	1996-03-18
CA2164847C (en)	2005-11-15
EP0702683B1 (de)	2003-09-17
SK154795A3 (en)	1996-07-03

Publication	Publication Date	Title
NO313331B1 (no)	2002-09-16	O6-alkylguaninderivater, fremgangsmåte for fremstilling og anvendelse derav samt farmasöytiske preparater
JP4127851B2 (ja)	2008-07-30	ピリミジン誘導体およびグアニン誘導体、ならびに腫瘍細胞の処置におけるそれらの使用
Zaki et al.	2006	Pyrazolopyranopyrimidines as a class of anti-inflammatory agents
SANEYOSHI et al.	1979	Synthetic nucleosides and nucleotides. XIII. Stannic chloride catalyzed ribosylation of several 6-substituted purines
US4287188A (en)	1981-09-01	Purine derivatives
Kazimierczuk et al.	1991	2′‐Deoxyisoguanosine and Base‐Modified Analogues: Chemical and Photochemical Synthesis
CZ20024273A3 (en)	2004-08-18	Substitution derivatives of n sp 6 sp -benzyladenosine, methods of their preparation, their use for preparation of drugs, cosmetic preparations and growth regulators, pharmaceutical preparations, cosmetic preparations and growth regulators containing these compounds
US6043228A (en)	2000-03-28	O6 -substituted guanine derivatives, a process for their preparation and their use in treating tumor cells
Plitta et al.	2012	New cytosine derivatives as inhibitors of DNA methylation
Krawczyk et al.	1995	Synthesis and antiproliferative and antiviral activity of 2'-deoxy-2'-fluoroarabinofuranosyl analogs of the nucleoside antibiotics toyocamycin and sangivamycin
Chen et al.	2003	Structure− activity relationships of (S, Z)-2-aminopurine methylenecyclopropane analogues of nucleosides. Variation of purine-6 substituents and activity against herpesviruses and hepatitis B virus
Kelley et al.	1989	Synthesis and structure-activity relationships of 2-substituted-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purines with antirhinovirus activity
Ge et al.	2024	Small molecular CD73 inhibitors: Recent progress and future perspectives
Piecyk et al.	2012	Synthesis of N2-modified 7-methylguanosine 5′-monophosphates as nematode translation inhibitors
Kolyachkina et al.	2011	N 6-Substituted adenosines. Cytokinin and antitumor activities
Hasan et al.	1992	Synthesis and biological studies of unsaturated acyclonucleoside analogs of S-adenosyl-L-homocysteine hydrolase inhibitors
US6677310B1 (en)	2004-01-13	Ring-expanded nucleosides and nucleotides
Mirkin et al.	1987	Cytotoxic action of adenosine nucleoside and dialdehyde analogues on murine neuroblastoma in tissue culture: structure-activity relationships
Kim et al.	2009	A new structural class of S-adenosylhomocysteine hydrolase inhibitors
IES940470A2 (en)	1994-12-14	O6-substituted guanine derivatives, a process for their preparation and their use in treating tumour cells
Chu et al.	1975	Synthesis and biological activity of some 8-substituted selenoguanosine cyclic 3', 5'-phosphates and related compounds
Sanghvi et al.	1989	Synteesis of Certain C-4 Substituted Pyrazolo [3, 4-b]-Pyridine Nucleosides Structurally Related to Adenosine and Inosine by Tee Sodiw Salt Glycosylation Procedure
Janson et al.	1992	Synthesis of Some Purine Carbocyclic Isosteres of 2′, 3′-Dideoxy-3′-C-Hydroxymethyl Nucleosides as Potential Inhibitors of HIV
Yüksek et al.	2022	Synthesis and Characterization of Novel Potential Biologically Active 3-Alkyl (Aryl)-4-(4-methylthiobenzylideneamino)-4, 5-dihidro-1H-1, 2, 4-triazol-5-ones
O'Sullivan	2019	An improved synthesis of adefovir and related analogues