5'-O-<<<<<(phosphono)methyl>oxy>carbonyl>amino>sulfonyl>-3'-azidothymidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-<<<<<(phosphono)methyl>oxy>carbonyl>amino>sulfonyl>-3'-azidothymidine
• 英文别名: [(2s,3s,5r)-3-Azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxysulfonylcarbamoyloxymethylphosphonic acid；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxysulfonylcarbamoyloxymethylphosphonic acid
• 化学式: C₁₂H₁₇N₆O₁₁PS
• 分子量: 484.34
• InChiKey: DHCZRVNDLUWZNF-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  221
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  齐多夫定 在 吡啶 、 三甲基溴硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 5'-O-<<<<<(phosphono)methyl>oxy>carbonyl>amino>sulfonyl>-3'-azidothymidine
  参考文献：
  名称：

  The Synthesis and Biological Evaluation of Sulfamoyl Nucleosides Related to Carbovir and AZT

  摘要：

  A series of 5'-(O) under bar-sulfamoylated carbocyclic 2',3'-dideoxy nucleosides was synthesized and evaluated for antitumor and anti-HIN activities. In this study, we have combined the phosphate mimicking features of the sulfamoyl group with our previously reported antiviral carbocyclic nucleoside, carbovir. In a related strategy, the sufamoyl moiety was used as a replacement for the alpha-phosphate of AZT-triphosphate in an analog designed to examine a membrane permeable HIV reverse transcriptase inhibitor. Some of the analogs exhibited significant in vitro anticancer activity.

  DOI：

  10.1080/15257779508010723

文献信息

• The Synthesis and Biological Evaluation of Sulfamoyl Nucleosides Related to Carbovir and AZT
  作者：Robert Vince、Phuong T. Pham

  DOI：10.1080/15257779508010723

  日期：1995.11

  A series of 5'-(O) under bar-sulfamoylated carbocyclic 2',3'-dideoxy nucleosides was synthesized and evaluated for antitumor and anti-HIN activities. In this study, we have combined the phosphate mimicking features of the sulfamoyl group with our previously reported antiviral carbocyclic nucleoside, carbovir. In a related strategy, the sufamoyl moiety was used as a replacement for the alpha-phosphate of AZT-triphosphate in an analog designed to examine a membrane permeable HIV reverse transcriptase inhibitor. Some of the analogs exhibited significant in vitro anticancer activity.