(2S,3R)-3-(6-aminopurin-9-yl)-2-(benzyloxy)-5-(3-methylphenyl)pentane | 201211-22-5

• 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-(benzyloxy)-5-(3-methylphenyl)pentane
• 英文别名: 9-[(3R,4S)-1-(3-methylphenyl)-4-phenylmethoxypentan-3-yl]purin-6-amine
• CAS: 201211-22-5
• 化学式: C₂₄H₂₇N₅O
• 分子量: 401.511
• InChiKey: FCNLFLSFZUQORZ-GHTZIAJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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-(benzyloxy)-5-(3-methylphenyl)pentane 在 palladium dihydroxide 环己烯 作用下， 以 乙醇 为溶剂， 以62%的产率得到(2S,3R)-3-(6-aminopurin-9-yl)-5-(3-methylphenyl)pentan-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：

  6-氯嘌呤 在 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-3-(6-aminopurin-9-yl)-2-(benzyloxy)-5-(3-methylphenyl)pentane
  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 aralkyladenines (ARADS)
  作者：Mark A. Curtis、Vaibhav Varkhedkar、Palle V.P. Pragnacharyulu、Elie Abushanab

  DOI：10.1016/s0960-894x(98)00291-1

  日期：1998.7

  Several 9-aralkyladenines have been prepared and their ADA inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C3') was found essential for potent activity. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.