ethyl (1R,2S)-1-({[(3R,5S,8S)-8-butyl-7,10-dioxo-22-phenyl-2,11-dioxa-6,9,21-triazatetracyclo[15.6.2.1-3,6-.0-20,24-]hexacosa-1(23),17,19,21,24-pentaen-5-yl]carbonyl}amino)-2-vinylcyclopropanecarboxylate | 1020094-62-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (1R,2S)-1-({[(3R,5S,8S)-8-butyl-7,10-dioxo-22-phenyl-2,11-dioxa-6,9,21-triazatetracyclo[15.6.2.1-3,6-.0-20,24-]hexacosa-1(23),17,19,21,24-pentaen-5-yl]carbonyl}amino)-2-vinylcyclopropanecarboxylate
• CAS: 1020094-62-5
• 化学式: C₄₀H₄₈N₄O₇
• 分子量: 696.844
• InChiKey: DDIJNCRVRUKJSG-DOUMTDSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  136.16
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl (1R,2S)-1-({[(3R,5S,8S)-8-butyl-7,10-dioxo-22-phenyl-2,11-dioxa-6,9,21-triazatetracyclo[15.6.2.1-3,6-.0-20,24-]hexacosa-1(23),17,19,21,24-pentaen-5-yl]carbonyl}amino)-2-vinylcyclopropanecarboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 18.0h， 以87%的产率得到(1R,2S)-1-({[(3R,5S,8S)-8-butyl-7,10-dioxo-22-phenyl-2,11-dioxa-6,9,21-triazatetracyclo[15.6.2.1-3,6-.0-20,24-]hexacosa-1(23),17,19,21,24-pentaen-5-yl]carbonyl}amino)-2-vinylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Molecular Modeling Based Approach to Potent P2−P4 Macrocyclic Inhibitors of Hepatitis C NS3/4A Protease

  摘要：

  Molecular modeling of inhibitor bound full length HCV NS3/4A protease structures proved to be a valuable tool in the design of a new series of potent NS3 protease inhibitors. Optimization of initial compounds provided 25a. The in vitro activity and selectivity as well as the rat pharmacokinetic profile of 25a compare favorably with the data for other NS3/4A protease inhibitors currently in clinical development for the treatment of HCV.

  DOI：

  10.1021/ja711120r
• 作为产物：
  描述：

  (1R,2S)-1-氨基-2-乙烯基-环丙羧酸乙酯盐酸盐(1:1) 、 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl (1R,2S)-1-({[(3R,5S,8S)-8-butyl-7,10-dioxo-22-phenyl-2,11-dioxa-6,9,21-triazatetracyclo[15.6.2.1-3,6-.0-20,24-]hexacosa-1(23),17,19,21,24-pentaen-5-yl]carbonyl}amino)-2-vinylcyclopropanecarboxylate
  参考文献：
  名称：

  Molecular Modeling Based Approach to Potent P2−P4 Macrocyclic Inhibitors of Hepatitis C NS3/4A Protease

  摘要：

  Molecular modeling of inhibitor bound full length HCV NS3/4A protease structures proved to be a valuable tool in the design of a new series of potent NS3 protease inhibitors. Optimization of initial compounds provided 25a. The in vitro activity and selectivity as well as the rat pharmacokinetic profile of 25a compare favorably with the data for other NS3/4A protease inhibitors currently in clinical development for the treatment of HCV.

  DOI：

  10.1021/ja711120r