3'-azido-3'-deoxythymidine 5'-2,3-dimethylhemisuccinate | 339577-85-4

• 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'-2,3-dimethylhemisuccinate
• CAS: 339577-85-4
• 化学式: C₁₆H₂₁N₅O₇
• 分子量: 395.372
• InChiKey: ZTLHPXOFFVTSQH-JEDMMJBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  176.45
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 、 3'-azido-3'-deoxythymidine 5'-2,3-dimethylhemisuccinate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 KNI-681
  参考文献：
  名称：

  A new class of anti-HIV agents: Synthesis and activity of conjugates of HIV protease inhibitors with a reverse transcriptase inhibitor

  摘要：

  Conjugates of HIV protease inhibitors with a reverse transcriptase inhibitor were synthesized, which expressed excellent: antiviral activity compared with that of the individual components. The remarkable antiviral activity of the conjugated compounds may be due to their penetration into the cell and later splitting into two different classes of anti-HIV agents. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00089-x
• 作为产物：
  描述：

  meso 2,3-dimethylsuccinic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3'-azido-3'-deoxythymidine 5'-2,3-dimethylhemisuccinate
  参考文献：
  名称：

  Synthesis and biological evaluation of prodrug-type anti-HIV agents: ester conjugates of carboxylic acid-containing dipeptide HIV protease inhibitors and a reverse transcriptase inhibitor

  摘要：

  On the basis of substrate transition-state mimic concept of HIV protease, a series of small-sized dipeptide inhibitors containing hydrophilic carboxyl group were designed and synthesized. These dipeptide inhibitors showed good HIV protease inhibitory activity, but their anti-HIV activity was poor. The low antiviral activities of these inhibitors were probably due to their inadequate cell membrane permeability caused by the presence of a free carboxylic acid in the inhibitors. Based on the prodrug concept as well as the combination of two different classes of anti-HIV agents, conjugates of HIV protease inhibitors with a nucleoside reverse transcriptase inhibitor were synthesized. Some of these conjugates exhibited excellent antiviral activity compared with that of individual inhibitors. The synergistic enhancement of anti-HIV activities of these conjugates may be due to their ability to penetrate into the target cell and subsequent regeneration of two different classes of anti-HIV agents in the cytoplasm. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00261-3