Phosphoric acid mono-{2-[1-(6-amino-purin-9-yl)-meth-(E)-ylidene]-cyclopropylmethyl} ester | 766506-58-5

• 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: Phosphoric acid mono-{2-[1-(6-amino-purin-9-yl)-meth-(E)-ylidene]-cyclopropylmethyl} ester
• 英文别名: [(2E)-2-[(6-aminopurin-9-yl)methylidene]cyclopropyl]methyl dihydrogen phosphate
• CAS: 766506-58-5
• 化学式: C₁₀H₁₂N₅O₄P
• 分子量: 297.21
• InChiKey: SUADPSNZQYDTBM-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Phosphoric acid mono-{2-[1-(6-amino-purin-9-yl)-meth-(E)-ylidene]-cyclopropylmethyl} ester 在 三丁基焦磷酸铵 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 72.0h， 生成 (E)-synadenol triphosphate
  参考文献：
  名称：

  Inhibition of Human Immunodeficiency Virus Reverse Transcriptase by Synadenol Triphosphate and Its E-Isomer

  摘要：

  Triphosphate 1c is a potent competitive inhibitor of wild-type HIV-1 reverse transcriptase with K-i close to ddATP. The E-isomer 2c is about 30-times weaker. Triphosphates le and 2c interact with the same active site of reverse transcriptase as ddATP. The extent of inhibition of two mutant forms of reverse transcriptase (RT), RTM184V and RTM184I, with triphosphate 1c was about 5 and 8 times lower than that of wild-type RTwt.

  DOI：

  10.1021/jm030048y
• 作为产物：
  描述：

  在 吡啶 、 三甲基氯硅烷 、 碘 作用下， 以64%的产率得到Phosphoric acid mono-{2-[1-(6-amino-purin-9-yl)-meth-(E)-ylidene]-cyclopropylmethyl} ester
  参考文献：
  名称：

  Inhibition of Human Immunodeficiency Virus Reverse Transcriptase by Synadenol Triphosphate and Its E-Isomer

  摘要：

  Triphosphate 1c is a potent competitive inhibitor of wild-type HIV-1 reverse transcriptase with K-i close to ddATP. The E-isomer 2c is about 30-times weaker. Triphosphates le and 2c interact with the same active site of reverse transcriptase as ddATP. The extent of inhibition of two mutant forms of reverse transcriptase (RT), RTM184V and RTM184I, with triphosphate 1c was about 5 and 8 times lower than that of wild-type RTwt.

  DOI：

  10.1021/jm030048y