(Z)-2-amino-6-methylamino-9-{[2,2-bis(hydroxymethyl)cyclopropylidene]methyl}purine | 1383125-48-1

• 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: (Z)-2-amino-6-methylamino-9-{[2,2-bis(hydroxymethyl)cyclopropylidene]methyl}purine
• 英文别名: [(2Z)-2-[[2-amino-6-(methylamino)purin-9-yl]methylidene]-1-(hydroxymethyl)cyclopropyl]methanol
• CAS: 1383125-48-1
• 化学式: C₁₂H₁₆N₆O₂
• 分子量: 276.298
• InChiKey: VCFGTNFPCPOBPZ-CLTKARDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-amino-6-chloro-9-{[2,2-bis(acetoxymethyl)cyclopropylidene]methyl}purine 在 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 32.5h， 生成 (Z)-2-amino-6-methylamino-9-{[2,2-bis(hydroxymethyl)cyclopropylidene]methyl}purine
  参考文献：
  名称：

  Synthesis and antiviral activity of certain second generation methylenecyclopropane nucleosides

  摘要：

  A second-generation series of substituted methylenecyclopropane nucleosides (MCPNs) has been synthesized and evaluated for antiviral activity against a panel of human herpesviruses, and for cytotoxicity. Although alkylated 2,6-diaminopurine analogs showed little antiviral activity, the compounds containing ether and thioether substituents at the 6-position of the purine did demonstrate potent and selective antiviral activity against several different human herpesviruses. In the 6-alkoxy series, antiviral activity depended on the length of the ether carbon chain, with the optimum chain length being about four carbon units long. For the corresponding thioethers, compounds containing secondary thioethers were more potent than those with primary thioethers. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.049

文献信息

• Synthesis and antiviral activity of certain second generation methylenecyclopropane nucleosides
  作者：John D. Williams、Atiyya R. Khan、Emma A. Harden、Caroll B. Hartline、Geraldine M. Jefferson、Kathy A. Keith、Mark N. Prichard、Jiri Zemlicka、Norton P. Peet、Terry L. Bowlin

  DOI：10.1016/j.bmc.2012.04.049

  日期：2012.6

  A second-generation series of substituted methylenecyclopropane nucleosides (MCPNs) has been synthesized and evaluated for antiviral activity against a panel of human herpesviruses, and for cytotoxicity. Although alkylated 2,6-diaminopurine analogs showed little antiviral activity, the compounds containing ether and thioether substituents at the 6-position of the purine did demonstrate potent and selective antiviral activity against several different human herpesviruses. In the 6-alkoxy series, antiviral activity depended on the length of the ether carbon chain, with the optimum chain length being about four carbon units long. For the corresponding thioethers, compounds containing secondary thioethers were more potent than those with primary thioethers. (C) 2012 Elsevier Ltd. All rights reserved.