tert-butyl (S)-3-((((3aS,4S,6R,6aR)-6-(2-chloro-6-(4H-1,2,4-triazol-4-yl)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)thio)pyrrolidine-1-carboxylate | 1166841-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: tert-butyl (S)-3-((((3aS,4S,6R,6aR)-6-(2-chloro-6-(4H-1,2,4-triazol-4-yl)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)thio)pyrrolidine-1-carboxylate
• CAS: 1166841-03-7
• 化学式: C₂₄H₃₁ClN₈O₅S
• 分子量: 579.08
• InChiKey: OQJQZOKQRIONIO-SWQDORGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131.54
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-3-((((3aS,4S,6R,6aR)-6-(2-chloro-6-(4H-1,2,4-triazol-4-yl)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)thio)pyrrolidine-1-carboxylate 、 2-(4-联苯)乙胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  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