9-(2-hydroxyethoxymethyl)guanine phosphoromono-N,N-dimethylaminoethylamidate | 1400637-39-9

• 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: 9-(2-hydroxyethoxymethyl)guanine phosphoromono-N,N-dimethylaminoethylamidate
• 英文别名: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethoxy-N-[2-(dimethylamino)ethyl]phosphonamidic acid;azane
• CAS: 1400637-39-9
• 化学式: C₁₂H₂₂N₇O₅P*H₃N
• 分子量: 392.355
• InChiKey: PKYNESAQEBRMMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.89
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9-(2-hydroxyethoxymethyl)guanine phosphoromono-N,N-dimethylaminoethylamidate 在 potassium dihydrogenphosphate 、 potassium hydroxide 作用下， 以 aq. phosphate buffer 、 水 为溶剂， 反应 120.0h， 生成 阿昔洛韦
  参考文献：
  名称：

  Phosphoramidate derivatives of acyclovir: Synthesis and antiviral activity in HIV-1 and HSV-1 models in vitro

  摘要：

  The antiviral activity against HIV and HSV and the chemical stability of ACV phosphoramidate derivatives were studied. The phosphoramidates of ACV demonstrated moderate activity. The best compound appeared to be 9-(2-hydroxymethyl)guanine phosphoromonomorpholidate (7), which inhibited virus replication in pseudo-HIV-1 particles by 50% at 50 mu M. It also inhibited replication of wild-type HSV-1 (9.7 mu M) as well as an acyclovir-resistant strain (25 mu M). None of the synthesised compounds showed any cytotoxicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.008
• 作为产物：
  描述：

  阿昔洛韦 在 磷酸三乙酯 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 生成 9-(2-hydroxyethoxymethyl)guanine phosphoromono-N,N-dimethylaminoethylamidate
  参考文献：
  名称：

  Phosphoramidate derivatives of acyclovir: Synthesis and antiviral activity in HIV-1 and HSV-1 models in vitro

  摘要：

  The antiviral activity against HIV and HSV and the chemical stability of ACV phosphoramidate derivatives were studied. The phosphoramidates of ACV demonstrated moderate activity. The best compound appeared to be 9-(2-hydroxymethyl)guanine phosphoromonomorpholidate (7), which inhibited virus replication in pseudo-HIV-1 particles by 50% at 50 mu M. It also inhibited replication of wild-type HSV-1 (9.7 mu M) as well as an acyclovir-resistant strain (25 mu M). None of the synthesised compounds showed any cytotoxicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.008