(S)-2-({(R)-2-[1-(2,6-Diamino-purin-9-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-phenoxy-phosphorylamino)-propionic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-({(R)-2-[1-(2,6-Diamino-purin-9-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-phenoxy-phosphorylamino)-propionic acid methyl ester
• 英文别名: methyl (2S)-2-[[[(1R,2Z)-2-[(2,6-diaminopurin-9-yl)methylidene]cyclopropyl]methoxy-phenoxyphosphoryl]amino]propanoate
• 化学式: C₂₀H₂₄N₇O₅P
• 分子量: 473.428
• InChiKey: XHUFBJWIETZGNX-QFDUYNLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (S)-2-({(R)-2-[1-(2,6-Diamino-purin-9-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-phenoxy-phosphorylamino)-propionic acid methyl ester 在 亚硝酸特丁酯 、 溶剂黄146 作用下， 反应 60.0h， 以68%的产率得到(R,Z)-9-[2-(hydroxymethyl)cyclopropylidene]methylisoguanine (methylphenylphosphoryl)-P-N-L-alaninate
  参考文献：
  名称：

  Synthesis, antiviral, and antitumor activity of 2-substituted purine methylenecyclopropane analogues of nucleosides

  摘要：

  The Z- and E-2-fluoro- and 2-chloropurine methylenecyclopropanes 9a,b and 10a,b as well as enantiomeric Z-isoguanine methylenecyclopropanes 11a,b and their phenyl phosphoralaninate pronucleotides 11c,d were synthesized and their antiviral activity against several viruses was evaluated. Fluoro analogues 9a and 10a were active against human cytomegalovirus but they were cytotoxic at approximately the same concentrations. Chloro derivatives 9b and 10b were non-cytotoxic and effective against Epstein-Barr virus in Daudi cells. Isoguanine analogues 11a-d lacked antiviral activity but pronucleotides 11c,d were substrates for porcine liver esterase. From the group of 9a,b and 10a,b, the fluoro analogues 9a and 10a exhibited antitumor activity but only the Z-isomer 9a had a selective effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.052

文献信息

• Synthesis, antiviral, and antitumor activity of 2-substituted purine methylenecyclopropane analogues of nucleosides
  作者：Xinrong Qin、Xinchao Chen、Kun Wang、Lisa Polin、Earl R. Kern、John C. Drach、Elizabeth Gullen、Yung-Chi Cheng、Jiri Zemlicka

  DOI：10.1016/j.bmc.2005.09.052

  日期：2006.2

  The Z- and E-2-fluoro- and 2-chloropurine methylenecyclopropanes 9a,b and 10a,b as well as enantiomeric Z-isoguanine methylenecyclopropanes 11a,b and their phenyl phosphoralaninate pronucleotides 11c,d were synthesized and their antiviral activity against several viruses was evaluated. Fluoro analogues 9a and 10a were active against human cytomegalovirus but they were cytotoxic at approximately the same concentrations. Chloro derivatives 9b and 10b were non-cytotoxic and effective against Epstein-Barr virus in Daudi cells. Isoguanine analogues 11a-d lacked antiviral activity but pronucleotides 11c,d were substrates for porcine liver esterase. From the group of 9a,b and 10a,b, the fluoro analogues 9a and 10a exhibited antitumor activity but only the Z-isomer 9a had a selective effect. (c) 2005 Elsevier Ltd. All rights reserved.