(1R,2S,4S,5S)-4-(2-Chloro-6-cyclopentylamino-purin-9-yl)-1-hydroxymethyl-bicyclo[3.1.0]hexan-2-ol | 349459-73-0

• 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: (1R,2S,4S,5S)-4-(2-Chloro-6-cyclopentylamino-purin-9-yl)-1-hydroxymethyl-bicyclo[3.1.0]hexan-2-ol
• 英文别名: (1R,2S,4S,5S)-4-[2-chloro-6-(cyclopentylamino)purin-9-yl]-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol
• CAS: 349459-73-0
• 化学式: C₁₇H₂₂ClN₅O₂
• 分子量: 363.847
• InChiKey: JKXQVOVVTTUXHT-QLQJRFMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  96.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5S)-4-(2-Chloro-6-cyclopentylamino-purin-9-yl)-1-hydroxymethyl-bicyclo[3.1.0]hexan-2-ol 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以10 mg的产率得到(1R,2S,4S,5S)-4-(6-Cyclopentylamino-purin-9-yl)-1-hydroxymethyl-bicyclo[3.1.0]hexan-2-ol
  参考文献：
  名称：

  Ring-Constrained (N)-Methanocarba nucleosides as adenosine receptor agonists: independent 5′-Uronamide and 2′-deoxy modifications

  摘要：

  Novel methanocarba adenosine analogues, having the pseudo-ribose northern (N) conformation preferred at adenosine receptors (ARs), were synthesized and tested in binding assays. The 5'-uronamide modification preserved [N-6-(3-iodobenzyl)] or enhanced (N-6-methyl) affinity at A(3)ARs, while the 2'-deoxy modification reduced affinity and efficacy in a functional assay. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00213-x
• 作为产物：
  描述：

  (1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2,6-dichloropurin-9-yl)bicyclo[3.1.0]hexane 在 三氯化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.25h， 生成 (1R,2S,4S,5S)-4-(2-Chloro-6-cyclopentylamino-purin-9-yl)-1-hydroxymethyl-bicyclo[3.1.0]hexan-2-ol
  参考文献：
  名称：

  Ring-Constrained (N)-Methanocarba nucleosides as adenosine receptor agonists: independent 5′-Uronamide and 2′-deoxy modifications

  摘要：

  Novel methanocarba adenosine analogues, having the pseudo-ribose northern (N) conformation preferred at adenosine receptors (ARs), were synthesized and tested in binding assays. The 5'-uronamide modification preserved [N-6-(3-iodobenzyl)] or enhanced (N-6-methyl) affinity at A(3)ARs, while the 2'-deoxy modification reduced affinity and efficacy in a functional assay. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00213-x

文献信息

• Ring-Constrained (N)-Methanocarba nucleosides as adenosine receptor agonists: independent 5′-Uronamide and 2′-deoxy modifications
  作者：Kyeong Lee、Gnana Ravi、Xiao-duo Ji、Victor E Marquez、Kenneth A Jacobson

  DOI：10.1016/s0960-894x(01)00213-x

  日期：2001.5

  Novel methanocarba adenosine analogues, having the pseudo-ribose northern (N) conformation preferred at adenosine receptors (ARs), were synthesized and tested in binding assays. The 5'-uronamide modification preserved [N-6-(3-iodobenzyl)] or enhanced (N-6-methyl) affinity at A(3)ARs, while the 2'-deoxy modification reduced affinity and efficacy in a functional assay. Published by Elsevier Science Ltd.