(S)-3-[5-(1-Carboxy-1-methyl-ethoxy)-1H-indol-3-yl]-2-[(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-propionic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-3-[5-(1-Carboxy-1-methyl-ethoxy)-1H-indol-3-yl]-2-[(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-propionic acid
• 英文别名: 2-[[3-[(2S)-2-carboxy-2-[[1-cyclohexyl-2-(furan-3-yl)benzimidazole-5-carbonyl]amino]ethyl]-1H-indol-5-yl]oxy]-2-methylpropanoic acid
• 化学式: C₃₃H₃₄N₄O₇
• 分子量: 598.656
• InChiKey: HYOOWDZAVFLZET-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-羟基-L-色氨酸 在 盐酸 、 氯化亚砜 、 caesium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 生成 (S)-3-[5-(1-Carboxy-1-methyl-ethoxy)-1H-indol-3-yl]-2-[(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-propionic acid
  参考文献：
  名称：

  Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: discovery of benzimidazole 5-carboxylic amide derivatives with low-nanomolar potency

  摘要：

  Optimization of benzimidazole 5-carboxamide derivatives previously identified as specific inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) has led to the discovery of potent analogues that inhibit the enzyme at low-nanomolar concentrations. Greater than 800-fold improvement in potency from the original lead structure was achieved through the combined effects of conformational rigidification, molecular size extension and the identification of previously unexploited interactions. Furthermore, these inhibitors retain specificity for HCV polymerase relative to other viral and mammalian RNA polymerases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.032

文献信息

• Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: discovery of benzimidazole 5-carboxylic amide derivatives with low-nanomolar potency
  作者：Pierre L Beaulieu、Michael Bös、Yves Bousquet、Patrick DeRoy、Gulrez Fazal、Jean Gauthier、James Gillard、Sylvie Goulet、Ginette McKercher、Marc-André Poupart、Serge Valois、George Kukolj

  DOI：10.1016/j.bmcl.2003.12.032

  日期：2004.2

  Optimization of benzimidazole 5-carboxamide derivatives previously identified as specific inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) has led to the discovery of potent analogues that inhibit the enzyme at low-nanomolar concentrations. Greater than 800-fold improvement in potency from the original lead structure was achieved through the combined effects of conformational rigidification, molecular size extension and the identification of previously unexploited interactions. Furthermore, these inhibitors retain specificity for HCV polymerase relative to other viral and mammalian RNA polymerases. (C) 2003 Elsevier Ltd. All rights reserved.