faldaprevir | 1447044-38-3

• 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: faldaprevir
• 英文别名: (1R,2S)-1-[[(2S,4R)-4-[[8-bromo-2-[2-(isopropylamino)thiazol-4-yl]-7-methoxy-4-quinolyl]oxy]-1-[(2S)-2-[2-(cyclopentylamino)-2-oxo-ethyl]-3,3-dimethyl-butanoyl]pyrrolidine-2-carbonyl]amino]-2-vinyl-cyclopropanecarboxylic acid；(1R,2S)-1-[[(2S,4R)-4-[8-bromo-7-methoxy-2-[2-(propan-2-ylamino)-1,3-thiazol-4-yl]quinolin-4-yl]oxy-1-[(2S)-2-[2-(cyclopentylamino)-2-oxoethyl]-3,3-dimethylbutanoyl]pyrrolidine-2-carbonyl]amino]-2-ethenylcyclopropane-1-carboxylic acid
• CAS: 1447044-38-3
• 化学式: C₄₀H₅₁BrN₆O₇S
• 分子量: 839.851
• InChiKey: NORZYIYJSPKWOH-QYUJUKINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  200
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (S)-tert-butylsuccinic acid anhydride 在 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 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 faldaprevir
  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

• Peptide backbone replacement of hepatitis C virus NS3 serine protease C-terminal cleavage product analogs: Discovery of potent succinamide inhibitors
  作者：Murray D. Bailey、Josée Bordeleau、Michel Garneau、Mélissa Leblanc、Christopher T. Lemke、Jeff O’Meara、Peter W. White、Montse Llinàs-Brunet

  DOI：10.1016/j.bmcl.2013.05.045

  日期：2013.8

  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.