9-[(Z)-(R)-1-((S)-1-Benzyloxy-ethyl)-hept-3-enyl]-9H-purin-6-ylamine | 316373-84-9

• 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: 9-[(Z)-(R)-1-((S)-1-Benzyloxy-ethyl)-hept-3-enyl]-9H-purin-6-ylamine
• CAS: 316373-84-9
• 化学式: C₂₁H₂₇N₅O
• 分子量: 365.478
• InChiKey: DLJDZGYBEKVOBP-IJXJCHRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.85
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  9-[(Z)-(R)-1-((S)-1-Benzyloxy-ethyl)-hept-3-enyl]-9H-purin-6-ylamine 在 氨 、 sodium 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以75%的产率得到(2S,3R)-3-(6-aminopurin-9-yl)non-5Z-en-2-ol
  参考文献：
  名称：

  Adenosine Deaminase Inhibitors:  Synthesis and Biological Evaluation of Unsaturated, Aromatic, and Oxo Derivatives of (+)-erythro-9-(2‘S-Hydroxy-3‘R-nonyl)adenine [(+)-EHNA]

  摘要：

  The synthesis and biological evaluation of three classes of chain-modified derivatives of(+)EHNA are described. Among the 5',6'-unsaturated derivatives, the Z-isomer was the most potent inhibitor of adenosine deaminase (ADA) but 3-fold less active than (+)-EHNA. Several 9-aralkyladenines (ARADs) have been prepared, and their inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C-3') was found to be essential for ADA activity equal to or slightly greater than that of (+)EHNA. Finally, replacement of the C-5' carbon with an oxygen resulted in reduced potency.

  DOI：

  10.1021/jm0002533
• 作为产物：
  描述：

  (2S,3S)-2-benzyloxynon-5-yn-3-ol 在 Lindlar's catalyst 偶氮二甲酸二异丙酯 、 氨 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成 9-[(Z)-(R)-1-((S)-1-Benzyloxy-ethyl)-hept-3-enyl]-9H-purin-6-ylamine
  参考文献：
  名称：

  Adenosine Deaminase Inhibitors:  Synthesis and Biological Evaluation of Unsaturated, Aromatic, and Oxo Derivatives of (+)-erythro-9-(2‘S-Hydroxy-3‘R-nonyl)adenine [(+)-EHNA]

  摘要：

  The synthesis and biological evaluation of three classes of chain-modified derivatives of(+)EHNA are described. Among the 5',6'-unsaturated derivatives, the Z-isomer was the most potent inhibitor of adenosine deaminase (ADA) but 3-fold less active than (+)-EHNA. Several 9-aralkyladenines (ARADs) have been prepared, and their inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C-3') was found to be essential for ADA activity equal to or slightly greater than that of (+)EHNA. Finally, replacement of the C-5' carbon with an oxygen resulted in reduced potency.

  DOI：

  10.1021/jm0002533