3-hexadecoxypropoxy-[2-[2-(6-oxo-1H-purin-9-yl)ethoxy]ethyl]phosphinic acid | 1400889-67-9

• 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: 3-hexadecoxypropoxy-[2-[2-(6-oxo-1H-purin-9-yl)ethoxy]ethyl]phosphinic acid
• CAS: 1400889-67-9
• 化学式: C₂₈H₅₁N₄O₆P
• 分子量: 570.71
• InChiKey: PXLMVOFVVQGNTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  bis(hexadecyloxypropyl)phosphonoethoxyethylchloride 在 叠氮化锂 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 3-hexadecoxypropoxy-[2-[2-(6-oxo-1H-purin-9-yl)ethoxy]ethyl]phosphinic acid
  参考文献：
  名称：

  Synthesis and antiviral activities of hexadecyloxypropyl prodrugs of acyclic nucleoside phosphonates containing guanine or hypoxanthine and a (S)-HPMP or PEE acyclic moiety

  摘要：

  Hexadecyloxypropyl esters of acyclic nucleoside phosphonates containing guanine (G) or hypoxanthine (Hx) and a (S)-[3-hydroxy-2-(phosphonomethoxy)propyl] [(S)-HPMP] or 2-(2-phosphonoethoxy)ethyl (PEE) acyclic moiety have been prepared. The activity of the prodrugs was evaluated in vitro against different virus families. Whereas ester derivatives of PEEHx and (S)-HPMPHx were antivirally inactive, monoesters of PEEG, and mono- and diesters of (S)-HPMPG showed pronounced antiviral activity against vaccinia virus and/or herpesviruses. Monoesters of (S)-HPMPG emerged as the most potent and selective derivatives against these DNA viruses. None of the compounds were inhibitory against RNA viruses and retroviruses. Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.027

文献信息

• Synthesis and antiviral activities of hexadecyloxypropyl prodrugs of acyclic nucleoside phosphonates containing guanine or hypoxanthine and a (S)-HPMP or PEE acyclic moiety
  作者：Tomáš Tichý、Graciela Andrei、Robert Snoeck、Jan Balzarini、Martin Dračínský、Marcela Krečmerová

  DOI：10.1016/j.ejmech.2012.07.027

  日期：2012.9

  Hexadecyloxypropyl esters of acyclic nucleoside phosphonates containing guanine (G) or hypoxanthine (Hx) and a (S)-[3-hydroxy-2-(phosphonomethoxy)propyl] [(S)-HPMP] or 2-(2-phosphonoethoxy)ethyl (PEE) acyclic moiety have been prepared. The activity of the prodrugs was evaluated in vitro against different virus families. Whereas ester derivatives of PEEHx and (S)-HPMPHx were antivirally inactive, monoesters of PEEG, and mono- and diesters of (S)-HPMPG showed pronounced antiviral activity against vaccinia virus and/or herpesviruses. Monoesters of (S)-HPMPG emerged as the most potent and selective derivatives against these DNA viruses. None of the compounds were inhibitory against RNA viruses and retroviruses. Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.