methyl N-[(2S)-1-[(2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate | 1361249-12-8

• 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: methyl N-[(2S)-1-[(2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 1361249-12-8
• 化学式: C₂₀H₂₅N₇O₃
• 分子量: 411.464
• InChiKey: QTLWLBUJOKPYEQ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-[(2S)-1-[(2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以91%的产率得到methyl N-[(2S)-1-[(2S)-2-[5-(4-aminophenyl)-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and evaluation of non-dimeric HCV NS5A inhibitors

  摘要：

  Based on the symmetrical bidentate structure of the NS5A inhibitor BMS-790052, a series of new monodentate molecules were designed. The synthesis of 36 new non-dimeric NS5A inhibitors is reported along with their ability to block HCV replication in an HCV 1b replicon system. Among them compound 5a showed picomolar range activity along with an excellent selectivity index (SI > 90,000). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.023
• 作为产物：
  描述：

  tert-butyl (2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 15.0h， 生成 methyl N-[(2S)-1-[(2S)-2-[5-(4-azidophenyl)-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and evaluation of non-dimeric HCV NS5A inhibitors

  摘要：

  Based on the symmetrical bidentate structure of the NS5A inhibitor BMS-790052, a series of new monodentate molecules were designed. The synthesis of 36 new non-dimeric NS5A inhibitors is reported along with their ability to block HCV replication in an HCV 1b replicon system. Among them compound 5a showed picomolar range activity along with an excellent selectivity index (SI > 90,000). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.023

文献信息

• POTENT AND SELECTIVE INHIBITORS OF HEPATITIS C VIRUS
  申请人：Coats Steven J.

  公开号：US20130210774A1

  公开（公告）日：2013-08-15

  The present invention is directed to compounds, compositions and methods for treating or preventing hepatitis C virus (HCV) infection in human subjects or other animal hosts. The compounds are as also pharmaceutically acceptable, salts, prodrugs, and other derivatives thereof as pharmaceutical compositions and methods for treatment or prevention of HCV infection.

  本发明涉及化合物、组合物和方法，用于治疗或预防人类或其他动物宿主的丙型肝炎病毒（HCV）感染。这些化合物也可以作为药物组成物的药学上可接受的盐、前药和其他衍生物，用于治疗或预防HCV感染。
• [EN] POTENT AND SELECTIVE INHIBITORS OF HEPATITIS C VIRUS<br/>[FR] INHIBITEURS PUISSANTS ET SÉLECTIFS DU VIRUS DE L'HÉPATITE C
  申请人：RFS PHARMA LLC

  公开号：WO2012027712A3

  公开（公告）日：2012-06-21
• US8859595B2
  申请人：——

  公开号：US8859595B2

  公开（公告）日：2014-10-14
• US9181227B2
  申请人：——

  公开号：US9181227B2

  公开（公告）日：2015-11-10
• Synthesis and evaluation of non-dimeric HCV NS5A inhibitors
  作者：Franck Amblard、Hongwang Zhang、Longhu Zhou、Junxing Shi、Drew R. Bobeck、James H. Nettles、Satish Chavre、Tamara R. McBrayer、Philip Tharnish、Tony Whitaker、Steven J. Coats、Raymond F. Schinazi

  DOI：10.1016/j.bmcl.2013.02.023

  日期：2013.4

  Based on the symmetrical bidentate structure of the NS5A inhibitor BMS-790052, a series of new monodentate molecules were designed. The synthesis of 36 new non-dimeric NS5A inhibitors is reported along with their ability to block HCV replication in an HCV 1b replicon system. Among them compound 5a showed picomolar range activity along with an excellent selectivity index (SI > 90,000). (C) 2013 Elsevier Ltd. All rights reserved.