tert-butyl (2S,4R)-4-(8-chloro-2-ethoxyquinolin-4-yl)oxy-2-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]pyrrolidine-1-carboxylate | 874127-62-5

• 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: tert-butyl (2S,4R)-4-(8-chloro-2-ethoxyquinolin-4-yl)oxy-2-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 874127-62-5
• 化学式: C₂₈H₃₄ClN₃O₇
• 分子量: 560.047
• InChiKey: DWFCEUDJNLMKFC-TXMYXSAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4R)-4-(8-chloro-2-ethoxyquinolin-4-yl)oxy-2-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]pyrrolidine-1-carboxylate 在 甲醇 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1R,2S)-1-((2S,4R)-1-(tert-butoxycarbonyl)-4-((8-chloro-2-ethoxyquinolin-4-yl)oxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Hepatitis C inhibitor peptide analogs

  摘要：

  式（I）的化合物：其中R1、R2、R3、R4、R5、Y、n和m的定义如本文所述。这些化合物可用作HCV NS3蛋白酶的抑制剂。

  公开号：

  US20060019905A1
• 作为产物：
  描述：

  tert-butyl (2S,4S)-2-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]-4-hydroxypyrrolidine-1-carboxylate 在 4-二甲氨基吡啶 、 caesium carbonate 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 tert-butyl (2S,4R)-4-(8-chloro-2-ethoxyquinolin-4-yl)oxy-2-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Peptide backbone replacement of hepatitis C virus NS3 serine protease C-terminal cleavage product analogs: Discovery of potent succinamide inhibitors

  摘要：

  A number of potent peptidic inhibitors of the NS3 protease have been described in the literature based on a substrate-based approach. In an on-going effort to reduce the peptidic character of this class of inhibitors, two novel series of analogs have been prepared in which the usual P3 amino acid residue is replaced by a succinamide fragment. This new backbone modification not only reduces the peptidic nature of traditional inhibitors but also provides new SAR opportunities for the capping group. Optimization of each of these two series resulted in inhibitors with sub-nanomolar potencies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.045

文献信息

• US7696242B2
  申请人：——

  公开号：US7696242B2

  公开（公告）日：2010-04-13
• [EN] HEPATITIS C INHIBITOR PEPTIDE ANALOGS<br/>[FR] ANALOGUES PEPTIDIQUES INHIBITEURS DE L'HEPATITE C
  申请人：BOEHRINGER ENGELHEIM INTERNAT

  公开号：WO2006007708A1

  公开（公告）日：2006-01-26

  The invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5, Y, n and m are as defined herein. The compounds are useful for the treatment and prevention of hepatitis C viral infection in mammals by inhibiting HCV NS3 protease. The invention further relates to azalactone compounds of the formula (III) which can be reacted with an amide anion to produce the compounds of formula (I).