3'-azido-3'-deoxythymidine 5'-cyclohexyl ethoxycarbonylphosphonate

• 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: 3'-azido-3'-deoxythymidine 5'-cyclohexyl ethoxycarbonylphosphonate
• 英文别名: ethyl [[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-(cyclohexoxy)phosphoryl]formate；ethyl [[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-cyclohexyloxyphosphoryl]formate
• 化学式: C₁₉H₂₈N₅O₈P
• 分子量: 485.434
• InChiKey: BQHXCFYCXKDQLA-MTLPQABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  环己醇 、 3'-azido-3'-deoxythymidine 5'-(ethoxycarbonyl)phosphonate 在 吡啶 、 2,4,6-三异丙基苯磺酰氯 作用下， 反应 16.0h， 以54%的产率得到3'-azido-3'-deoxythymidine 5'-cyclohexyl ethoxycarbonylphosphonate
  参考文献：
  名称：

  New Phosphonoformic Acid Derivatives of 3′-Azido-3′-Deoxythymidine

  摘要：

  New 5'-alkyl ethoxy- and aminocarbonylphosphonates of 3'-azido-3'-deoxythymidine (AZT) were synthesized, and their antiviral properties in HIV-1-infected cell cultures and stability to chemical hydrolysis were studied. The AZT 5'-aminocarbonylphosphonates were shown to be significantly more stable in phosphate buffer (pH 7.2) than the corresponding ethoxycarbonylphosphonates. The therapeutic (selectivity) index of some of the compounds exceeded that of the parent AZT due to their higher antiviral activity.

  DOI：

  10.1023/b:rubi.0000030131.37092.0a

文献信息

• New Phosphonoformic Acid Derivatives of 3′-Azido-3′-Deoxythymidine
  作者：E. A. Shirokova、M. V. Jasko、A. L. Khandazhinskaya、A. V. Ivanov、D. V. Yanvarev、Yu. S. Skoblov、T. R. Pronyaeva、N. V. Fedyuk、A. G. Pokrovskii、M. K. Kukhanova

  DOI：10.1023/b:rubi.0000030131.37092.0a

  日期：2004.5

  New 5'-alkyl ethoxy- and aminocarbonylphosphonates of 3'-azido-3'-deoxythymidine (AZT) were synthesized, and their antiviral properties in HIV-1-infected cell cultures and stability to chemical hydrolysis were studied. The AZT 5'-aminocarbonylphosphonates were shown to be significantly more stable in phosphate buffer (pH 7.2) than the corresponding ethoxycarbonylphosphonates. The therapeutic (selectivity) index of some of the compounds exceeded that of the parent AZT due to their higher antiviral activity.