(1S,3R,4R)-3-(6-amino-purin-9-yl)-4-hydroxycyclopentanecarboxylic acid methyl ester | 956600-35-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1S,3R,4R)-3-(6-amino-purin-9-yl)-4-hydroxycyclopentanecarboxylic acid methyl ester
• 英文别名: (1S,3R,4R)-methyl 3-(6-amino-9H-purin-9-yl)-4-hydroxycyclopentanecarboxylate；methyl (1S,3R,4R)-3-(6-aminopurin-9-yl)-4-hydroxycyclopentane-1-carboxylate
• CAS: 956600-35-4
• 化学式: C₁₂H₁₅N₅O₃
• 分子量: 277.283
• InChiKey: PPWYJCNBNCRAPZ-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R)-3-(6-amino-purin-9-yl)-4-hydroxycyclopentanecarboxylic acid methyl ester 在 TEA 、 水 作用下， 反应 0.33h， 以100%的产率得到(1S,3R,4R)-3-(6-amino-purin-9-yl)-4-hydroxycyclopentanecarboxylic acid
  参考文献：
  名称：

  Carbocyclic 3′-deoxyadenosine-based highly potent bisubstrate-analog inhibitor of basophilic protein kinases

  摘要：

  Carbocyclic analogs of 3'-deoxyadenosine were synthesized as racemates and the resulting stereoisomers were separated by chromatography on a chiral column. The conjugation of obtained compounds with hexa-(D-arginine) via 6-aminohexanoic acid linker led to a highly potent inhibitor of several basophilic protein kinases with some selectivity towards cAMP-dependent protein kinase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.016
• 作为产物：
  描述：

  trans-6-oxa-bicyclo[3.1.0]hexane-3-carboxylic acid methyl ester 、 腺嘌呤 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (1S,3R,4R)-3-(6-amino-purin-9-yl)-4-hydroxycyclopentanecarboxylic acid methyl ester 、 (1R,3S,4S)-3-(6-amino-purin-9-yl)-4-hydroxycyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Carbocyclic 3′-deoxyadenosine-based highly potent bisubstrate-analog inhibitor of basophilic protein kinases

  摘要：

  Carbocyclic analogs of 3'-deoxyadenosine were synthesized as racemates and the resulting stereoisomers were separated by chromatography on a chiral column. The conjugation of obtained compounds with hexa-(D-arginine) via 6-aminohexanoic acid linker led to a highly potent inhibitor of several basophilic protein kinases with some selectivity towards cAMP-dependent protein kinase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.016