3'-azido-3'-deoxythymidine 5'-(ethoxycarbonyl)phosphonate | 725245-98-7

• 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'-(ethoxycarbonyl)phosphonate
• CAS: 725245-98-7
• 化学式: C₁₄H₂₀N₅O₈P
• 分子量: 417.315
• InChiKey: PCZJXVMCBFBBRZ-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  185.68
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3'-azido-3'-deoxythymidine 5'-(ethoxycarbonyl)phosphonate 在 Mitsunobu reagent system 作用下， 生成 Methylcarbamoylmethyl-phosphonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester ethyl ester
  参考文献：
  名称：

  New Lipophilic Derivatives of AZT and d4T 5′-Phosphonates

  摘要：

  5'-Aminocarbonylphosphonyl and aminocarbonylmethylphosphonyl diesters of AZT and d4T were synthesized as potential anti-HIV agents.

  DOI：

  10.1081/ncn-120022718
• 作为产物：
  描述：

  齐多夫定 、 pyridinium salt of ethoxycarbonylmethylphosphonic acid 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以69%的产率得到3'-azido-3'-deoxythymidine 5'-(ethoxycarbonyl)phosphonate
  参考文献：
  名称：

  Uncharged AZT and D4T Derivatives of Phosphonoformic and Phosphonoacetic Acids as Anti-HIV Pronucleosides

  摘要：

  Two series of new lipophilic phosphonoformate and phosphonoacetate derivatives of AZT and d4T were synthesized and evaluated as anti-HIV agents. The efficacy of some of the synthesized compounds in cell cultures infected with HIV-1 was higher than that of the parent nucleosides and only slightly correlated to their stability in the phosphate buffer and human blood serum. The synthesized phosphonates are most probably prodrug forms of the corresponding nucleosides.

  DOI：

  10.1021/jm0310176