(2R,3R,4S,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(((S)-pyrrolidin-3-ylthio)methyl)-tetrahydrofuran-3,4-diol | 1166840-97-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2R,3R,4S,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(((S)-pyrrolidin-3-ylthio)methyl)-tetrahydrofuran-3,4-diol
• 英文别名: (2S,3R,4S,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(((S)-pyrrolidin-3-ylthio)methyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5S)-2-(6-amino-2-chloropurin-9-yl)-5-[[(3S)-pyrrolidin-3-yl]sulfanylmethyl]oxolane-3,4-diol
• CAS: 1166840-97-6
• 化学式: C₁₄H₁₉ClN₆O₃S
• 分子量: 386.862
• InChiKey: CCGNITMZESBAEB-WFMPWKQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-tert-butyl 3-(((3aS,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)pyrrolidine-1-carboxylate 在 水 、 三氟乙酸 作用下， 生成 (2R,3R,4S,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(((S)-pyrrolidin-3-ylthio)methyl)-tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors

  摘要：

  Potent SAH analogues with constrained homocysteine units have been designed and synthesized as inhibitors of human DNMT enzymes. The five membered (2S,4S)-4-mercaptopyrrolidine-2-carboxylic acid, in 1a, was a good replacement for homocysteine, while the corresponding six-member counterpart was less active. Further optimization of 1a, changed the selectivity pro. le of these inhibitors. A Chloro substituent at the 2-position of 1a, compound 1d, retained potency against DNMT1, while N-6 alkylation, compound 7a, conserved DNMT3b2 activity. The concomitant substitutions of 1a at both 2- and N-6 positions reduced activity against both enzymes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.132