1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-(3,4,5-trimethoxybenzoyl) butanedioate | 313340-78-2

• 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: 1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-(3,4,5-trimethoxybenzoyl) butanedioate
• CAS: 313340-78-2
• 化学式: C₂₄H₂₇N₅O₁₁
• 分子量: 561.505
• InChiKey: KDHPPROGCBYRBA-BMGDILEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  齐多夫定 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-(3,4,5-trimethoxybenzoyl) butanedioate
  参考文献：
  名称：

  Synthesis of New Covalently Bound κ-Carrageenan−AZT Conjugates with Improved Anti-HIV Activities

  摘要：

  This paper describes the first covalent synthesis Of kappa-carrageenan-3'-azido-3'-deoxythymidine (AZT) conjugates. A succinate diester spacer was used to Covalently couple AZT onto kappa-carrageenan, resulting in a tripartite prodrug. Two methods (UV and radioactive counting) are described and validated to determine the AZT loading onto the kappa-carrageenan carrier. This polymeric carrier, through its own intrinsic anti-HIV activity, is expected to act not only as a drug delivery agent but also as an anti-HIV agent. Synergism between the two drugs (kappa-carrageenan and AZT) was demonstrated when MT-4 cells were preincubated with the kappa-earrageenan-AZT conjugate prior to HIV-1-infection. A threshold of AZT loaded onto the kappa-carrageenan was required to achieve this synergistic effect. Such kappa-carrageenan-AZT conjugates could be of great therapeutic interest because these conjugates, which contain a low AZT concentration, present improved anti-HIV activities relative to free AZT. Moreover, kappa-carrageenan is a well-tolerated biopolymer, already used in the food industry.

  DOI：

  10.1021/jm010969d

文献信息

• Synthesis of New Covalently Bound κ-Carrageenan−AZT Conjugates with Improved Anti-HIV Activities
  作者：Patrick Vlieghe、Thierry Clerc、Christophe Pannecouque、Myriam Witvrouw、Erik De Clercq、Jean-Pierre Salles、Jean-Louis Kraus

  DOI：10.1021/jm010969d

  日期：2002.3.1

  This paper describes the first covalent synthesis Of kappa-carrageenan-3'-azido-3'-deoxythymidine (AZT) conjugates. A succinate diester spacer was used to Covalently couple AZT onto kappa-carrageenan, resulting in a tripartite prodrug. Two methods (UV and radioactive counting) are described and validated to determine the AZT loading onto the kappa-carrageenan carrier. This polymeric carrier, through its own intrinsic anti-HIV activity, is expected to act not only as a drug delivery agent but also as an anti-HIV agent. Synergism between the two drugs (kappa-carrageenan and AZT) was demonstrated when MT-4 cells were preincubated with the kappa-earrageenan-AZT conjugate prior to HIV-1-infection. A threshold of AZT loaded onto the kappa-carrageenan was required to achieve this synergistic effect. Such kappa-carrageenan-AZT conjugates could be of great therapeutic interest because these conjugates, which contain a low AZT concentration, present improved anti-HIV activities relative to free AZT. Moreover, kappa-carrageenan is a well-tolerated biopolymer, already used in the food industry.