4-[(3R,5S)-5-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]oxy-7-methoxyquinoline-2-carboxylic acid | 687995-64-8

• 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: 4-[(3R,5S)-5-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]oxy-7-methoxyquinoline-2-carboxylic acid
• CAS: 687995-64-8
• 化学式: C₂₈H₃₃N₃O₉
• 分子量: 555.585
• InChiKey: RUSVITGOOQNARU-AJMOGZKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-[(3R,5S)-5-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]oxy-7-methoxyquinoline-2-carboxylic acid 在 盐酸 、 氢溴酸 、 三乙胺 、 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 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 21.5h， 生成 (1R,2S)-1-[[(2S,4R)-4-[2-(2-acetamido-1,3-thiazol-4-yl)-7-methoxyquinolin-4-yl]oxy-1-[(2S)-2-[2-(cyclopentylamino)-2-oxoethyl]-3,3-dimethylbutanoyl]pyrrolidine-2-carbonyl]amino]-2-ethenylcyclopropane-1-carboxylic acid
  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
• 作为产物：
  描述：

  methyl 4-[(3R,5S)-5-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]oxy-7-methoxyquinoline-2-carboxylate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 4-[(3R,5S)-5-[[(1R,2S)-2-ethenyl-1-methoxycarbonylcyclopropyl]carbamoyl]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]oxy-7-methoxyquinoline-2-carboxylic acid
  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

• Hepatitis C inhibitor compound
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20040229818A1

  公开（公告）日：2004-11-18

  Compounds of formula (I): 1 wherein B, X, R 3 , R 21 , R 22 , R 1 and R c are defined herein. The compounds are useful as inhibitors of HCV NS3 protease.

  式（I）的化合物：其中B、X、R3、R21、R22、R1和R在此处定义。这些化合物可用作HCV NS3蛋白酶的抑制剂。