ethyl (4R)-4-[(7-bromoisoquinolin-1-yl)oxy]-L-prolinate hydrochloride | 924271-69-2

• 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 (4R)-4-[(7-bromoisoquinolin-1-yl)oxy]-L-prolinate hydrochloride
• 英文别名: ethyl (2S,4R)-4-(7-bromoisoquinolin-1-yl)oxypyrrolidine-2-carboxylate;hydrochloride
• CAS: 924271-69-2
• 化学式: C₁₆H₁₇BrN₂O₃*ClH
• 分子量: 401.688
• InChiKey: KBECPGASQQGLIX-OJMBIDBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-N-[(pent-4-en-1-yloxy)carbonyl]-L-valine 、 ethyl (4R)-4-[(7-bromoisoquinolin-1-yl)oxy]-L-prolinate hydrochloride 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以80%的产率得到ethyl 3-methyl-N-[(pent-4-en-1-yloxy)carbonyl]-L-valyl-(4R)-4-[(7-bromoisoquinolin-1-yl)oxy]-L-prolinate
  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：

  (2S,4R)-4-((7-Bromoisoquinolin-1-yl)oxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 、 乙醇 在 盐酸 作用下， 反应 24.0h， 以57.0 g的产率得到ethyl (4R)-4-[(7-bromoisoquinolin-1-yl)oxy]-L-prolinate hydrochloride
  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