9-[2-(1-phosphonobutan-2-yloxy)ethyl]adenine | 1330633-23-2

• 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: 9-[2-(1-phosphonobutan-2-yloxy)ethyl]adenine
• 英文别名: 2-[2-(6-Aminopurin-9-yl)ethoxy]butylphosphonic acid
• CAS: 1330633-23-2
• 化学式: C₁₁H₁₈N₅O₄P
• 分子量: 315.269
• InChiKey: WCQVFDLLFVDKQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  diethyl 9-[2-(1-phosphonobutan-2-yloxy)ethyl]-6-chloropurine 在 三甲基溴硅烷 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 30.0h， 生成 9-[2-(1-phosphonobutan-2-yloxy)ethyl]adenine
  参考文献：
  名称：

  Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity

  摘要：

  Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy) ethyl (PEE) chain bearing various substituents in beta-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivatives exhibit antiviral activity against HIV and vaccinia virus (middle micromolar range), HSV-1 and HSV-2 (lower micromolar range) and VZV and CMV (nanomolar range), although the parent unbranched PEE-ANPs are inactive. Adenine as a nucleobase and the methyl group attached to the PEE chain proved to be a prerequisite to afford pronounced antiviral activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.045

文献信息

• Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
  作者：Dana Hocková、Antonín Holý、Graciela Andrei、Robert Snoeck、Jan Balzarini

  DOI：10.1016/j.bmc.2011.06.045

  日期：2011.8

  Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy) ethyl (PEE) chain bearing various substituents in beta-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivatives exhibit antiviral activity against HIV and vaccinia virus (middle micromolar range), HSV-1 and HSV-2 (lower micromolar range) and VZV and CMV (nanomolar range), although the parent unbranched PEE-ANPs are inactive. Adenine as a nucleobase and the methyl group attached to the PEE chain proved to be a prerequisite to afford pronounced antiviral activity. (C) 2011 Elsevier Ltd. All rights reserved.