benzyl (2S)-4-(7-methoxy-2-phenylquinolin-4-yl)oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate | 1108656-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: benzyl (2S)-4-(7-methoxy-2-phenylquinolin-4-yl)oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1108656-97-8
• 化学式: C₃₂H₃₄N₂O₆
• 分子量: 542.632
• InChiKey: JITJPTZIGDUTOS-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-4-(7-methoxy-2-phenylquinolin-4-yl)oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate 在 盐酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 ethyl (1R,2S)-1-((S)-2-(3-(hept-6-en-1-yl)-3-methylureido)-4-((7-methoxy-2-phenylquinolin-4-yl)oxy)butanamido)-2-vinylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis and antiviral evaluation of a novel series of homoserine-based inhibitors of the hepatitis C virus NS3/4A serine protease

  摘要：

  We disclose here the synthesis of a series of macrocyclic HCV protease inhibitors, where the homoserine linked together the quinoline P2' motif and the macrocyclic moiety. These compounds exhibit potent inhibitory activity against HCV NS3/4A protease and replicon cell based assay. Their enzymatic and antiviral activities are modulated by substitutions on the quinoline P2' at position 8 by methyl and halogens and by small heterocycles at position 2. The in vitro structure activity relationship (SAR) studies and in vivo pharmacokinetic (PK) evaluations of selected compounds are described herein. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.020
• 作为产物：
  描述：

  7-methoxy-2-phenylquinolin-4-ol 、 (S)-2-[[(叔丁氧羰基)氨基]-4-羟基丁酸苄酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 benzyl (2S)-4-(7-methoxy-2-phenylquinolin-4-yl)oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
  参考文献：
  名称：

  [EN] MACROCYCLIC SERINE PROTEASE INHIBITORS
  [FR] INHIBITEURS MACROCYCLIQUES DE LA SÉRINE PROTÉASE

  摘要：

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，Formula I的药物组合物，以及其制备方法。还提供了它们用于治疗宿主HCV感染的方法。

  公开号：

  WO2009014730A1

文献信息

• [EN] MACROCYCLIC SERINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS MACROCYCLIQUES DE LA SÉRINE PROTÉASE
  申请人：IDENIX PHARMACEUTICALS INC

  公开号：WO2009014730A1

  公开（公告）日：2009-01-29

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，Formula I的药物组合物，以及其制备方法。还提供了它们用于治疗宿主HCV感染的方法。
• MACROCYCLIC SERINE PROTEASE INHIBITORS I
  申请人：Parsy Christophe Claude

  公开号：US20090047244A1

  公开（公告）日：2009-02-19

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，公式I所示的化合物，包含这种化合物的制药组合物以及其制备过程。同时，还提供了它们用于治疗宿主中HCV感染的方法。
• WO2007/1406
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and antiviral evaluation of a novel series of homoserine-based inhibitors of the hepatitis C virus NS3/4A serine protease
  作者：François-René Alexandre、Guillaume Brandt、Catherine Caillet、Dominique Chaves、Thierry Convard、Michel Derock、Damien Gloux、Yann Griffon、Lisa Lallos、Frédéric Leroy、Michel Liuzzi、Anna-Giulia Loi、Laure Moulat、Chiara Musiu、Christophe Parsy、Houcine Rahali、Virginie Roques、Maria Seifer、David Standring、Dominique Surleraux

  DOI：10.1016/j.bmcl.2015.07.020

  日期：2015.9

  We disclose here the synthesis of a series of macrocyclic HCV protease inhibitors, where the homoserine linked together the quinoline P2' motif and the macrocyclic moiety. These compounds exhibit potent inhibitory activity against HCV NS3/4A protease and replicon cell based assay. Their enzymatic and antiviral activities are modulated by substitutions on the quinoline P2' at position 8 by methyl and halogens and by small heterocycles at position 2. The in vitro structure activity relationship (SAR) studies and in vivo pharmacokinetic (PK) evaluations of selected compounds are described herein. (C) 2015 Elsevier Ltd. All rights reserved.