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5-脱氧-5-(甲基氨基)-2,3-O-(1-甲基亚乙基)-腺苷酸 | 34245-49-3

分子结构分类

有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类

中文名称

5-脱氧-5-(甲基氨基)-2,3-O-(1-甲基亚乙基)-腺苷酸

中文别名

——

英文名称

5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine

英文别名

5'-deoxy-2',3'-O-isopropylidene-5'-(N-methylamino)adenosine；5'-deoxy-5'-(methylamino)-2',3'-O-isopropylideneadenosine；2'3'-O-isopropylidene-5'-deoxy-5'-methylaminoadenosine；5'-deoxy-5'-methylamino-2',3'-isopropylideneadenosine；5'-methylamino-O^2'_,O3'-isopropylidene-5'-deoxy-adenosine；9-((3aR,4R,6R,6aR)-2,2-dimethyl-6-((methylamino)methyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine；9-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(methylaminomethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-amine

CAS

34245-49-3

化学式

C₁₄H₂₀N₆O₃

mdl

——

分子量

320.351

InChiKey

SJXNSGJHLDXAIO-QYVSTXNMSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

537.5±60.0 °C(Predicted)
密度：

1.66±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-0.6
重原子数：

23
可旋转键数：

3
环数：

4.0
sp3杂化的碳原子比例：

0.64
拓扑面积：

109
氢给体数：

2
氢受体数：

8

安全信息

储存条件：

储存条件：2-8°C，避光，惰性气体保护。

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
2',3'-异丙叉腺苷	2',3'-isopropylidene adenosine	362-75-4	C₁₃H₁₇N₅O₄	307.309
——	5'-deoxy-5'-chloro-2',3'-isopropylideneadenosine	24514-56-5	C₁₃H₁₆ClN₅O₃	325.755
——	((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methanesulfonate	68179-90-8	C₁₄H₁₉N₅O₆S	385.401
5'-O-(苄基磺酰基)-2',3'-O-异亚丙基腺苷	((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate	5605-63-0	C₂₀H₂₃N₅O₆S	461.499

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]propan-1-ol	121032-08-4	C₁₇H₂₆N₆O₄	378.431
——	5'-deoxy-2',3'-O-isopropylidene-5'-[(2-hydroxyethyl)methylamino]adenosine	121032-10-8	C₁₆H₂₄N₆O₄	364.404
——	5'-deoxy-5'-N-methyl-N'-(4-butyric acid)-2',3'-O,O-(1-methylethylidene)adenosine	1192143-73-9	C₁₈H₂₆N₆O₅	406.442
——	5'-[(3-aminopropyl)methylamino]-5'-deoxy-2',3'-O-isopropylideneadenosine	121032-11-9	C₁₇H₂₇N₇O₃	377.446
——	5'-deoxy-5'-[(2-carboethoxyethyl)methylamino]-2',3'-O-isopropylideneadenosine	1106914-12-8	C₁₉H₂₈N₆O₅	420.469
——	N'-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-N,N'-dimethylethane-1,2-diamine	1381761-00-7	C₁₇H₂₇N₇O₃	377.446
——	N1-(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-N1,3-dimethylbutane-1,3-diamine	1381764-08-4	C₁₉H₃₁N₇O₃	405.5
——	9-[(3aR,4R,6R,6aR)-6-[[[4-(aminomethyl)phenyl]methyl-methylamino]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-amine	478161-10-3	C₂₂H₂₉N₇O₃	439.517
——	4-[[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]methyl]benzonitrile	478161-08-9	C₂₂H₂₅N₇O₃	435.486
——	9-[(3aR,4R,6R,6aR)-6-[[[2-(aminomethyl)phenyl]methyl-methylamino]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-amine	478161-11-4	C₂₂H₂₉N₇O₃	439.517
——	2-[[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]methyl]benzonitrile	478161-09-0	C₂₂H₂₅N₇O₃	435.486
——	1-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)propyl)-3-(4-chlorophenyl)urea	1381764-30-2	C₂₄H₃₁ClN₈O₄	531.014
——	1-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea	1381761-28-9	C₂₇H₃₈N₈O₄	538.65
——	benzyl (3-((((3aR,4R,6R,6aR)-6-(6-amino-911-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)carbamate	1380350-54-8	C₂₆H₃₃N₇O₅	523.592
——	1-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea	1381760-93-5	C₂₈H₄₀N₈O₄	552.677
——	3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]propyl N-(4-tert-butylphenyl)carbamate	1381761-13-2	C₂₈H₃₉N₇O₅	553.662
——	1-[2-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]ethyl]-3-(4-tert-butylphenyl)urea	1381781-39-0	C₂₇H₃₈N₈O₄	538.65
——	1-(4-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)butan-2-yl)-3-(4-(tert-butyl)phenyl)urea	1381764-18-6	C₂₉H₄₂N₈O₄	566.704
——	1-[2-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]ethyl]-3-(4-tert-butylphenyl)-1-methylurea	1381761-01-8	C₂₈H₄₀N₈O₄	552.677
——	1-[3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]propyl]-3-[4-(3-methylphenyl)phenyl]urea	1381761-49-4	C₃₁H₃₈N₈O₄	586.694
——	1-[3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]propyl]-3-[4-(2-aminophenoxy)phenyl]urea	1381761-40-5	C₃₀H₃₇N₉O₅	603.681
——	1-((R)-1-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)pentan-3-yl)-3-(4-(tert-butyl)phenyl)urea	1381761-82-5	C₃₀H₄₄N₈O₄	580.731
——	1-((S)-1-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)pentan-3-yl)-3-(4-(tert-butyl)phenyl)urea	1381761-93-8	C₃₀H₄₄N₈O₄	580.731
——	1-[3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]propyl]-3-(4-cyclohexylphenyl)urea	1381761-42-7	C₃₀H₄₂N₈O₄	578.715
——	1-[3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]-2,2-dimethylpropyl]-3-(4-tert-butylphenyl)urea	1381761-23-4	C₃₀H₄₄N₈O₄	580.731
——	1-[[1-[[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]methyl]cyclopropyl]methyl]-3-(4-tert-butylphenyl)urea	1381761-26-7	C₃₀H₄₂N₈O₄	578.715
——	(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-((methyl((Z)-4-propionamidobut-2-en-1-yl)amino)methyl)tetrahydrofuran-3,4-diyl diacetate	——	C₂₂H₃₁N₇O₆	489.531
——	(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-((((Z)-4-butyramidobut-2-en-1-yl)(methyl)amino)methyl)tetrahydrofuran-3,4-diyl diacetate	——	C₂₃H₃₃N₇O₆	503.558
——	2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)propyl)isoindoline-1,3-dione	1381763-61-6	C₂₅H₂₉N₇O₅	507.549
——	5'-deoxy-5'-N-methyl-N-[4-{(S)-2-(N-tert-butoxycarbonyl)amino-butyric acid}] benzyl ester-2',3'-O,O-(1-methylethylidene)adenosine	1129995-73-8	C₃₀H₄₁N₇O₇	611.698
——	1-[3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]propyl]-3-[4-(1,3-thiazol-4-yl)phenyl]urea	1381761-44-9	C₂₇H₃₃N₉O₄S	579.683
——	(4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one	176847-64-6	C₂₇H₃₃N₇O₇	567.602
N(4)-腺苷-N(4)-甲基-2,4-二氨基丁酸	5'-[N-[(3S)-3-amino-3-carboxypropyl]-N-methylamino]-5'-deoxyadenosine	111770-79-7	C₁₅H₂₃N₇O₅	381.392
——	N⁴-(5'-adenosyl)-N⁴-methyl-2-(R,S),4-diaminobutanoic acid	129828-73-5	C₁₅H₂₃N₇O₅	381.392
——	N-((Z)-4-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)but-2-en-1-yl)acetamide	——	C₁₇H₂₅N₇O₄	391.43
——	N-((Z)-4-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)but-2-en-1-yl)butyramide	——	C₁₉H₂₉N₇O₄	419.484
——	(9H-fluoren-9-yl)methyl (2-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)ethyl)carbamate	1381760-70-8	C₃₁H₃₅N₇O₅	585.663
——	1-(3-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)propyl)-3-(4-chlorophenyl)urea	1381764-31-3	C₂₁H₂₇ClN₈O₄	490.95
——	1-(3-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)propyl)-3-(3-chlorophenyl)urea	1381764-29-9	C₂₁H₂₇ClN₈O₄	490.95
——	1-[2-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylamino]ethyl]-3-[(4-tert-butylphenyl)methyl]urea	1381760-84-4	C₂₅H₃₆N₈O₄	512.612
——	1-(3-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)propyl)-3-(3,4-dichlorophenyl)urea	1381764-34-6	C₂₁H₂₆Cl₂N₈O₄	525.395
——	1-(3-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea	1381760-94-6	C₂₅H₃₆N₈O₄	512.612
——	3-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylamino]propyl N-(4-tert-butylphenyl)carbamate	1381761-14-3	C₂₅H₃₅N₇O₅	513.597
——	1-[2-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylamino]ethyl]-3-(4-tert-butylphenyl)urea	1381781-41-4	C₂₄H₃₄N₈O₄	498.585
——	1-[3-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylamino]propyl]-3-[4-(3-methylphenyl)phenyl]urea	1381761-50-7	C₂₈H₃₄N₈O₄	546.629
——	1-[2-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylamino]ethyl]-3-(4-tert-butylphenyl)-1-methylurea	1381761-02-9	C₂₅H₃₆N₈O₄	512.612
——	1-[3-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylamino]propyl]-3-(4-cyclohexylphenyl)urea	1381761-43-8	C₂₇H₃₈N₈O₄	538.65
——	9H-fluoren-9-ylmethyl N-[2-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylamino]ethyl]carbamate	1381760-71-9	C₂₈H₃₁N₇O₅	545.598

反应信息

作为反应物：

描述：

5-脱氧-5-(甲基氨基)-2,3-O-(1-甲基亚乙基)-腺苷酸在三光气、 N,N-二异丙基乙胺作用下，以甲醇、二氯甲烷为溶剂，反应 2.0h，生成 1-[3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-methylamino]propyl]-3-[4-(2-nitrophenoxy)phenyl]urea

参考文献：

名称：

[EN] MODULATORS OF HISTONE METHYLTRANSFERASE, AND METHODS OF USE THEREOF
[FR] MODULATEURS D'HISTONE MÉTHYLTRANSFÉRASE ET LEURS PROCÉDÉS D'UTILISATION

摘要：

公开号：

WO2012082436A3
作为产物：

描述：

N-(((3αR,4R,6R,6αR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-N-methyl-2-nitrobenzenesulfonamide 在 caesium carbonate 、苯硫酚作用下，以乙腈为溶剂，反应 20.0h，以69%的产率得到5-脱氧-5-(甲基氨基)-2,3-O-(1-甲基亚乙基)-腺苷酸

参考文献：

名称：

An acyl-SAM analog as an affinity ligand for identifying quorum sensing signal synthases

摘要：

我们在这里报告了利用与酶抑制剂共轭的珠子亲和纯化N-酰基脱氨酪氨酸乳酸合成酶，该酶抑制剂是基于催化中间体酰基-SAM设计的。

DOI：

10.1039/c4cc03094j

点击查看最新优质反应信息

文献信息

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics

作者：Yongzhi Gao、Matthijs J. van Haren、Ned Buijs、Paolo Innocenti、Yurui Zhang、Davide Sartini、Roberto Campagna、Monica Emanuelli、Richard B. Parsons、Willem Jespers、Hugo Gutiérrez-de-Terán、Gerard J. P. van Westen、Nathaniel I. Martin

DOI：10.1021/acs.jmedchem.1c01094

日期：2021.9.9

the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary

烟酰胺N-甲基转移酶 (NNMT) 将烟酰胺（维生素 B3）甲基化以生成 1-甲基烟酰胺 (MNA)。NNMT 过表达与多种疾病有关，最突出的是人类癌症，表明其作为治疗靶点的潜力。近年来，小分子 NNMT 抑制剂的开发引起了人们的兴趣，其中最有效的抑制剂具有基于烟酰胺底物和S-腺苷-l-甲硫氨酸 (SAM) 辅因子元素的结构特征。我们在这里报告了新的双底物抑制剂的开发，其中包括缺电子的芳族基团来模拟烟酰胺部分。此外，一个跨发现 - 烯烃接头最适合连接这些抑制剂中的底物和辅因子模拟物。鉴定出的最有效的 NNMT 抑制剂的 IC 50值为 3.7 nM，使其成为迄今为止报道的最活跃的 NNMT 抑制剂之一。补充分析技术、建模研究和基于细胞的检测提供了对这些抑制剂的结合模式、亲和力和选择性的深入了解。
Synthesis and evaluation of analogs of 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (MDL 73811, or AbeAdo) – An inhibitor of S-adenosylmethionine decarboxylase with antitrypanosomal activity

作者：Anthony J. Brockway、Oleg A. Volkov、Casey C. Cosner、Karen S. MacMillan、Stephen A. Wring、Thomas E. Richardson、Michael Peel、Margaret A. Phillips、Jef K. De Brabander

DOI：10.1016/j.bmc.2017.07.063

日期：2017.10

describe our efforts to improve the pharmacokinetic properties of a mechanism-based suicide inhibitor of the polyamine biosynthetic enzyme S-adenosylmethionine decarboxylase (AdoMetDC), essential for the survival of the eukaryotic parasite Trypanosoma brucei responsible for Human African Trypanosomiasis (HAT). The lead compound, 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (1, also known

我们描述了我们为改善基于机制的多胺生物合成酶S-腺苷甲硫氨酸脱羧酶（AdoMetDC）的自杀抑制剂的药代动力学特性而做出的努力，这对于负责人类非洲锥虫病（HAT）的真核寄生虫布鲁氏锥虫的生存至关重要。前导化合物5'-（（（（Z）-4-氨基-2-丁烯基）甲基氨基）-5'-脱氧腺苷（1，也称为MDL 73811或AbeAdo，在HAT的淋巴模型中以低剂量具有疗效，但由于血脑屏障渗透性差，在HAT的CNS期小鼠模型中未显示出明显的作用。因此，我们制备并评估了一系列在氨基丁烯基侧链，5'-胺，核糖和嘌呤片段上有修饰的类似物。尽管我们从这个全面的数据集中获得了有价值的结构活性见解，但我们并没有在保持中枢化合物1的强抗寄生虫活性和代谢稳定性的同时改善中枢神经系统渗透的前景。
5'deoxy-5'-substituted adenosines

申请人：Southern Research Institute

公开号：US04794174A1

公开（公告）日：1988-12-27

In accordance with this invention, there are provided 5'-deoxy-5'-substituted adenosines having the formula ##STR1## wherein X is a member selected from the group consisting of NH, NCH.sub.3, S, or ##STR2## n is an integer from 2-4; and Z is a member selected from the group consisting of: ##STR3## provided that when X is NH, S or CH.sub.3 --S .sym., then Z is not ONH.sub.2. These compounds show activity as inhibitors of AdoMet-DC.

根据这一发明，提供了具有以下结构的5'-去氧-5'-取代腺苷：其中X是从NH、NCH3、S或n为2-4的整数；Z是从以下组成的成员中选择的：但当X为NH、S或CH3-S时，Z不是ONH2。这些化合物显示出作为AdoMet-DC抑制剂的活性。
Synthesis and Evaluation of Analogues of 5‘-([(Z)-4-Amino-2-butenyl]methylamino)-5‘-deoxyadenosine as Inhibitors of Tumor Cell Growth, Trypanosomal Growth, and HIV-1 Infectivity

作者：Canio J. Marasco,、Debora L. Kramer、John Miller、Carl W. Porter、Cyrus J. Bacchi、Donna Rattendi、Louis Kucera、Nathan Iyer、Ralph Bernacki、Paula Pera、Janice R. Sufrin

DOI：10.1021/jm0201621

日期：2002.11.1

antineoplastic activity of 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine. However, di-O-acetylation of the parent compound produced a potential prodrug that caused markedly pronounced inhibition of trypanosomal and neoplastic cell growth and viability. Moreover, the acetylated derivative of 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine did inhibit HIV-1 growth and infectivity

设计并合成了一系列明确定义的5'-（[（（Z）-4-氨基-2-丁烯基]甲基氨基）-5'-脱氧腺苷类似物，以进一步确定抑制S-腺苷甲硫氨酸脱羧酶的最佳结构要求并有可能增强甚至分离它们的抗增殖和抗锥虫活性。大多数结构修饰对5'-（[（（Z）-4-氨基-2-丁烯基]甲基氨基）-5'-脱氧腺苷的抗锥虫活性和抗肿瘤活性均具有有害影响。但是，母体化合物的二-O-乙酰化作用会产生潜在的前药，从而显着抑制锥虫和肿瘤细胞的生长和活力。此外，5'-（[[（Z）-4-氨基-2-丁烯基]甲基氨基）-5'-脱氧腺苷的乙酰化衍生物确实抑制了HIV-1的生长和感染力，
[EN] SUBSTITUTED PURINE AND 7 - DEAZAPURINE COMPOUNDS AS MODULATORS OF EPIGENETIC ENZYMES [FR] COMPOSÉS PURINES ET 7-DÉAZAPURINES SUBSTITUÉES EN TANT QUE MODULATEURS D'ENZYMES ÉPIGÉNIQUES

申请人：EPIZYME INC

公开号：WO2012075381A1

公开（公告）日：2012-06-07

The present invention relates to substituted purine and 7-deazapurine compounds. The present invention also relates to pharmaceutical compositions containing these compounds and methods of treating disorders in which DOTl -mediated protein methylation plays a part, such as cancer and neurological disorders, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

本发明涉及替代嘌呤和7-去氮嘌呤化合物。本发明还涉及含有这些化合物的药物组合物以及通过向需要的受试者施用这些化合物和药物组合物来治疗DOT1介导的蛋白甲基化在内的疾病的方法，例如癌症和神经系统疾病。