(2S,4S)-methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-1-methylpyrrolidine-2-carboxylate | 901776-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S)-methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-1-methylpyrrolidine-2-carboxylate
• 英文别名: methyl (2S,4S)-4-[[(3aR,4R,6S,6aS)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methylsulfanyl]-1-methylpyrrolidine-2-carboxylate
• CAS: 901776-41-8
• 化学式: C₂₀H₂₈N₆O₅S
• 分子量: 464.546
• InChiKey: KKEFYAKBTSXSMR-AEFKHOGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,4S)-methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-1-methylpyrrolidine-2-carboxylate 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 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
• 作为产物：
  描述：

  (2S,4S)-methyl 4-(acetylthio)-1-methylpyrrolidine-2-carboxylate 、 5'-O-(苄基磺酰基)-2',3'-O-异亚丙基腺苷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.25h， 以24%的产率得到(2S,4S)-methyl 4-(((3aS,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylthio)-1-methylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Inhibitors of DNA Methyltransferase

  摘要：

  这项发明涉及抑制DNA甲基转移酶亚型DNMT1和DNMT3b2。该发明提供了用于抑制DNMT1和DNMT3b2的化合物和方法。

  公开号：

  US20080132525A1