(2S,3R)-3-(6-aminopurin-9-yl)-2-benzyloxynon-5-yne | 316373-74-7

• 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: (2S,3R)-3-(6-aminopurin-9-yl)-2-benzyloxynon-5-yne
• 英文别名: 9-[(2S,3R)-2-phenylmethoxynon-5-yn-3-yl]purin-6-amine
• CAS: 316373-74-7
• 化学式: C₂₁H₂₅N₅O
• 分子量: 363.462
• InChiKey: NCJVGTCQQZDGLJ-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(6-aminopurin-9-yl)-2-benzyloxynon-5-yne 在 Lindlar's catalyst 氢气 作用下， 以 甲苯 为溶剂， 以92%的产率得到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
• 作为产物：
  描述：

  (2S,3S)-3-benzyloxy-1,2-epoxybutane 在 正丁基锂 、 dilithium tetrachlorocuprate 、 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 50.0h， 生成 (2S,3R)-3-(6-aminopurin-9-yl)-2-benzyloxynon-5-yne
  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

文献信息

• Adenosine deaminase inhibitors. Synthesis and biological evaluation of chain modified analogs of (+)-EHNA
  作者：Palle V.P. Pragnacharyulu、Pei-Jung Lu、Elie Abushanab

  DOI：10.1016/0960-894x(96)00439-8

  日期：1996.10

  Unsaturated chain modified analogs of (+)-EHNA have been prepared and evaluated as inhibitors of adenosine deaminase. The geometry appears to play a role in binding to the enzyme. (C) 1996 Elsevier Science Ltd.
• Adenosine Deaminase Inhibitors:  Synthesis and Biological Evaluation of Unsaturated, Aromatic, and Oxo Derivatives of (+)-<i>e</i><i>rythro</i>-9-(2‘<i>S</i>-Hydroxy-3‘<i>R</i>-nonyl)adenine [(+)-EHNA]
  作者：Palle V. P. Pragnacharyulu、Vaibhav Varkhedkar、Mark A. Curtis、I. F. Chang、Elie Abushanab

  DOI：10.1021/jm0002533

  日期：2000.11.1

  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.