2-Methoxycarbonylmethyl-3H-benzoimidazole-5-carboxylic acid methyl ester | 524940-55-4

• 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: 2-Methoxycarbonylmethyl-3H-benzoimidazole-5-carboxylic acid methyl ester
• 英文别名: methyl 2-(2-methoxy-2-oxoethyl)-3H-benzimidazole-5-carboxylate
• CAS: 524940-55-4
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: AJDHMUDAJAKMLU-UHFFFAOYSA-N

物化性质

• 沸点：
  462.9±25.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.28
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-Methoxycarbonylmethyl-3H-benzoimidazole-5-carboxylic acid methyl ester 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N-氟代双苯磺酰胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-{[2-({6-[1-(1-Carboxy-2-phosphono-ethylcarbamoyl)-2-phosphono-ethylcarbamoyl]-1-methyl-1H-benzoimidazol-2-yl}-difluoro-methyl)-3H-benzoimidazole-5-carbonyl]-amino}-3-phosphono-propionic acid
  参考文献：
  名称：

  Highly potent non-peptidic inhibitors of the HCV NS3/NS4A serine protease

  摘要：

  Screening of a diverse set of bisbenzimidazoles for inhibition of the hepatitis C virus (HCV) serine protease NS3/NS4A led to the identification of a potent Zn2+-dependent inhibitor (1). Optimization of this screening hit afforded a 10-fold more potent inhibitor (46) under Zn2+ conditions (K-i = 27 nM). This compound (46) binds also to NS3/NS4A in a Zn2+ independent fashion (K-i = 1 muM). The SAR of this class of compounds under Zn2+ conditions is highly divergent compared to the SAR in the absence of Zn2+, suggesting two distinct binding modes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00680-7
• 作为产物：
  描述：

  Methoxy-cyan-essigsaeure-methylester 、 3,4-二氨基苯甲酸甲酯 以 乙醇 为溶剂， 以77%的产率得到2-Methoxycarbonylmethyl-3H-benzoimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Highly potent non-peptidic inhibitors of the HCV NS3/NS4A serine protease

  摘要：

  Screening of a diverse set of bisbenzimidazoles for inhibition of the hepatitis C virus (HCV) serine protease NS3/NS4A led to the identification of a potent Zn2+-dependent inhibitor (1). Optimization of this screening hit afforded a 10-fold more potent inhibitor (46) under Zn2+ conditions (K-i = 27 nM). This compound (46) binds also to NS3/NS4A in a Zn2+ independent fashion (K-i = 1 muM). The SAR of this class of compounds under Zn2+ conditions is highly divergent compared to the SAR in the absence of Zn2+, suggesting two distinct binding modes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00680-7