3'-azido-3'-deoxythymidine 5'-(aminocarbonylmethyl)phosphonate | 725246-06-0

• 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'-(aminocarbonylmethyl)phosphonate
• CAS: 725246-06-0
• 化学式: C₁₂H₁₇N₆O₇P
• 分子量: 388.277
• InChiKey: MMEARMUCPYZQBS-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  202.47
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  环己醇 、 3'-azido-3'-deoxythymidine 5'-(aminocarbonylmethyl)phosphonate 在 三苯基氯硅烷 作用下， 生成 Carbamoylmethyl-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 cyclohexyl 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：

  3'-azido-3'-deoxythymidine 5'-(ethoxycarbonyl)phosphonate 在 氨 作用下， 生成 3'-azido-3'-deoxythymidine 5'-(aminocarbonylmethyl)phosphonate
  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

文献信息

• Uncharged AZT and D4T Derivatives of Phosphonoformic and Phosphonoacetic Acids as Anti-HIV Pronucleosides
  作者：Elena A. Shirokova、Maxim V. Jasko、Anastasiya L. Khandazhinskaya、Alexander V. Ivanov、Dmitry V. Yanvarev、Yury S. Skoblov、Vladimir A. Mitkevich、Eduard V. Bocharov、Tatyana R. Pronyaeva、Nina V. Fedyuk、Marina K. Kukhanova、Andrey G. Pokrovsky

  DOI：10.1021/jm0310176

  日期：2004.7.1

  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.