1-cyclohexyl-N-[(1S)-2-(5-hydroxy-1H-indol-3-yl)-1-thiazol-4-yl-ethyl]-2-phenyl-benzimidazole-5-carboxamide | 390810-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-cyclohexyl-N-[(1S)-2-(5-hydroxy-1H-indol-3-yl)-1-thiazol-4-yl-ethyl]-2-phenyl-benzimidazole-5-carboxamide
• 英文别名: 1-cyclohexyl-N-[(1S)-2-(5-hydroxy-1H-indol-3-yl)-1-(1,3-thiazol-4-yl)ethyl]-2-phenylbenzimidazole-5-carboxamide
• CAS: 390810-67-0
• 化学式: C₃₃H₃₁N₅O₂S
• 分子量: 561.707
• InChiKey: IKWNEEUTOVQSFE-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-环己基-2-苯基苯并咪唑-5-羧酸 、 3-[(2S)-2-amino-2-(1,3-thiazol-4-yl)ethyl]-1H-indol-5-ol 在 DIEA 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-cyclohexyl-N-[(1S)-2-(5-hydroxy-1H-indol-3-yl)-1-thiazol-4-yl-ethyl]-2-phenyl-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Benzimidazole Thumb Pocket I finger-loop inhibitors of HCV NS5B polymerase: Improved drug-like properties through C-2 SAR in three sub-series

  摘要：

  SAR at the C-2 position of benzimidazole-based Thumb Pocket I inhibitors of HCV NS5B polymerase revealed parallel activity for distinct sub-series that harbor 5-hydroxytryptophan amides, neutral thiazole isosteres or recently disclosed cinnamic acid diamides. The consistent SAR among the three sub-series suggest a common binding mode to the Thumb Pocket I allosteric site. New inhibitors with submicromolar cell-based replicon potency and improved 'drug-like' features are disclosed along with preliminary characterization of their ADME-PK profile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.003

文献信息

• Benzimidazole Thumb Pocket I finger-loop inhibitors of HCV NS5B polymerase: Improved drug-like properties through C-2 SAR in three sub-series
  作者：Pierre L. Beaulieu、Nathalie Dansereau、Jianmin Duan、Michel Garneau、James Gillard、Ginette McKercher、Steven LaPlante、Lisette Lagacée、Louise Thauvette、George Kukolj

  DOI：10.1016/j.bmcl.2010.02.003

  日期：2010.3

  SAR at the C-2 position of benzimidazole-based Thumb Pocket I inhibitors of HCV NS5B polymerase revealed parallel activity for distinct sub-series that harbor 5-hydroxytryptophan amides, neutral thiazole isosteres or recently disclosed cinnamic acid diamides. The consistent SAR among the three sub-series suggest a common binding mode to the Thumb Pocket I allosteric site. New inhibitors with submicromolar cell-based replicon potency and improved 'drug-like' features are disclosed along with preliminary characterization of their ADME-PK profile. (C) 2010 Elsevier Ltd. All rights reserved.