diethyl 9-[2-(3-benzyloxy-1-phosphonopropan-2-yloxy)ethyl]-6-chloropurine | 1330633-15-2

• 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: diethyl 9-[2-(3-benzyloxy-1-phosphonopropan-2-yloxy)ethyl]-6-chloropurine
• CAS: 1330633-15-2
• 化学式: C₂₁H₂₈ClN₄O₅P
• 分子量: 482.904
• InChiKey: QAKQYCYCOQDLGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  97.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  diethyl 9-[2-(3-benzyloxy-1-phosphonopropan-2-yloxy)ethyl]-6-chloropurine 在 水 、 三氟乙酸 作用下， 以67%的产率得到diethyl 9-[2-(3-benzyloxy-1-phosphonopropan-2-yloxy)ethyl]hypoxanthine
  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
• 作为产物：
  描述：

  甲基膦酸二乙酯 在 正丁基锂 、 硼烷四氢呋喃络合物 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 生成 diethyl 9-[2-(3-benzyloxy-1-phosphonopropan-2-yloxy)ethyl]-6-chloropurine
  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