2',3'-dideoxy-3'-thiacytidine-5'-ethoxycarbonylphosphonate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2',3'-dideoxy-3'-thiacytidine-5'-ethoxycarbonylphosphonate
• 英文别名: [(2S,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy-ethoxycarbonyl-phosphinic acid；[(2S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy-ethoxycarbonylphosphinic acid
• 化学式: C₁₁H₁₆N₃O₇PS
• 分子量: 365.304
• InChiKey: KPSFSKZFNZNTMH-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2',3'-dideoxy-3'-thiacytidine-5'-ethoxycarbonylphosphonate 在 吡啶 、 氨 作用下， 以 水 为溶剂， 反应 12.0h， 以121 mg的产率得到2',3'-dideoxy-3'-thiacytidine-5'-aminocarbonylphosphonate
  参考文献：
  名称：

  5′-Phosphonate Derivatives of 2′,3′-Dideoxy-3′-Thiacytidine as New Anti-HIV Prodrugs

  摘要：

  Two new phosphonate 3TC prodrugs were synthesized and studied in MT‐4 cells as inhibitors of HIV replication. Their pharmacokinetic parameters were evaluated following intragastric administration in rabbits and oral administration in dogs. Both compounds were much less toxic than parent 3TC in cell cultures and could generate the active nucleoside in laboratory animals.

  DOI：

  10.1111/j.1747-0285.2011.01129.x
• 作为产物：
  描述：

  pyridinium salt of ethoxycarbonylphosphonic acid 、 ent-拉米夫定 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 18.0h， 以85%的产率得到2',3'-dideoxy-3'-thiacytidine-5'-ethoxycarbonylphosphonate
  参考文献：
  名称：

  5′-Phosphonate Derivatives of 2′,3′-Dideoxy-3′-Thiacytidine as New Anti-HIV Prodrugs

  摘要：

  Two new phosphonate 3TC prodrugs were synthesized and studied in MT‐4 cells as inhibitors of HIV replication. Their pharmacokinetic parameters were evaluated following intragastric administration in rabbits and oral administration in dogs. Both compounds were much less toxic than parent 3TC in cell cultures and could generate the active nucleoside in laboratory animals.

  DOI：

  10.1111/j.1747-0285.2011.01129.x

文献信息

• 5′-Phosphonate Derivatives of 2′,3′-Dideoxy-3′-Thiacytidine as New Anti-HIV Prodrugs
  作者：Anastasia L. Khandazhinskaya、Maxim V. Jasko、Inna L. Karpenko、Pavel N. Solyev、Natalia A. Golubeva、Marina K. Kukhanova

  DOI：10.1111/j.1747-0285.2011.01129.x

  日期：2011.7

  Two new phosphonate 3TC prodrugs were synthesized and studied in MT‐4 cells as inhibitors of HIV replication. Their pharmacokinetic parameters were evaluated following intragastric administration in rabbits and oral administration in dogs. Both compounds were much less toxic than parent 3TC in cell cultures and could generate the active nucleoside in laboratory animals.