| 500755-73-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• CAS: 500755-73-7
• 化学式: C₂₆H₃₅N₅O₁₂
• 分子量: 609.59
• InChiKey: HXHBIAMOANWVRW-PLARXQPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  211.6
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到AZT D-glucopyranose-3-O-succinyl ester
  参考文献：
  名称：

  Synthesis and in vitro chemical and enzymatic stability of glycosyl 3′-azido-3′-deoxythymidine derivatives as potential anti-HIV agents

  摘要：

  New glycosyl derivatives of 3'-azido-3'-deoxythymidine (AZT) (1 and 2) were synthesized in order to improve AZT retention in the blood and to guarantee its sustained release, overcoming the necessity of multiple drug administrations. The esters synthesized (1 and 2) link AZT, by a succinyl linker, to the C-3 position of glucose and to C-6 of galactose. Furthermore, the chemical and enzymatic stabilities of esters 1 and 2 were evaluated in order to determine both their stability in aqueous medium and their feasibility to undergo enzymatic cleavage by esterase to regenerate the original drug. The pharmacokinetic profiles of esters 1 and 2, obtained after systemic administration, showed an interesting controlled release, in particular for ester 2, compared to the pharmacokinetic profile of AZT. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00080-5
• 作为产物：
  描述：

  3-O-(3-carboxypropanoyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 、 齐多夫定 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以73%的产率得到
  参考文献：
  名称：

  Synthesis and in vitro chemical and enzymatic stability of glycosyl 3′-azido-3′-deoxythymidine derivatives as potential anti-HIV agents

  摘要：

  New glycosyl derivatives of 3'-azido-3'-deoxythymidine (AZT) (1 and 2) were synthesized in order to improve AZT retention in the blood and to guarantee its sustained release, overcoming the necessity of multiple drug administrations. The esters synthesized (1 and 2) link AZT, by a succinyl linker, to the C-3 position of glucose and to C-6 of galactose. Furthermore, the chemical and enzymatic stabilities of esters 1 and 2 were evaluated in order to determine both their stability in aqueous medium and their feasibility to undergo enzymatic cleavage by esterase to regenerate the original drug. The pharmacokinetic profiles of esters 1 and 2, obtained after systemic administration, showed an interesting controlled release, in particular for ester 2, compared to the pharmacokinetic profile of AZT. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00080-5