9-[(2-hydroxyethoxy)methyl]guanine (3-hexadecyloxypropyl) phosphate sodium salt

• 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-hydroxyethoxy)methyl]guanine (3-hexadecyloxypropyl) phosphate sodium salt
• 英文别名: 1-O-hexadecylpropanediol-3-phospho-ACV；sodium;2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl 3-hexadecoxypropyl phosphate
• 化学式: C₂₇H₄₉N₅O₇P*Na
• 分子量: 609.679
• InChiKey: PYTRZSGYVQQOLA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  41
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  阿昔洛韦 在 吡啶 、 1H-1,2,4-三唑 、 N-甲基咪唑 、 sodium hydroxide 、 三甲基氯硅烷 、 水 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.67h， 生成 9-[(2-hydroxyethoxy)methyl]guanine (3-hexadecyloxypropyl) phosphate sodium salt
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 1-O-Hexadecylpropanediol-3-P-acyclovir: Efficacy Against HSV-1 Infection in Mice

  摘要：

  We synthesized, 1-O-hexadecylpropanediol-3-P-acyclovir, an orally bioavailable lipid prodrug of acyclovir and evaluated it for in vitro and in vivo activity against herpes simplex virus infections. Although 1-O-hexadecylpropanediol-3-P-acyclovir was less active in vitro than acyclovir, on a molar basis it was 2.4 times more active orally in preventing mortality from acute HSV-I infection in mice. In vitro, 1-O-hexadecylpropanediol-3-P-acyclovir was also more active than acyclovir in a thymidine kinase negative mutant strain of HSV-1 (DM21) and had somewhat higher activity in cytomegalovirus infection in vitro due to it's ability to bypass thymidine kinase.

  DOI：

  10.1080/15257770008033022

文献信息

• Synthesis and Antiviral Evaluation of 1-O-Hexadecylpropanediol-3-P-acyclovir: Efficacy Against HSV-1 Infection in Mice
  作者：James R. Beadle、Ganesh D. Kini、Kathy A. Aldern、Michael F. Gardner、Kristine N. Wright、Rachel J. Rybak、Earl R. Kern、Karl Y. Hostetler

  DOI：10.1080/15257770008033022

  日期：2000.1

  We synthesized, 1-O-hexadecylpropanediol-3-P-acyclovir, an orally bioavailable lipid prodrug of acyclovir and evaluated it for in vitro and in vivo activity against herpes simplex virus infections. Although 1-O-hexadecylpropanediol-3-P-acyclovir was less active in vitro than acyclovir, on a molar basis it was 2.4 times more active orally in preventing mortality from acute HSV-I infection in mice. In vitro, 1-O-hexadecylpropanediol-3-P-acyclovir was also more active than acyclovir in a thymidine kinase negative mutant strain of HSV-1 (DM21) and had somewhat higher activity in cytomegalovirus infection in vitro due to it's ability to bypass thymidine kinase.