ethyl 3-(3-((4-methylbenzo[b]thiophen-3-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propanoate | 1325147-72-5

• 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: ethyl 3-(3-((4-methylbenzo[b]thiophen-3-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propanoate
• CAS: 1325147-72-5
• 化学式: C₂₂H₂₂N₂O₃S
• 分子量: 394.494
• InChiKey: MBCUTOSTJILXEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.23
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(3-((4-methylbenzo[b]thiophen-3-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propanoate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到3-{3-[(4-methyl-1-benzothien-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}propanoic acid
  参考文献：
  名称：

  Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region

  摘要：

  A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P-1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P-1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P-1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.126
• 作为产物：
  描述：

  丙烯酸乙酯 在 盐酸 、 苄基三甲基氢氧化铵 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 3-(3-((4-methylbenzo[b]thiophen-3-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propanoate
  参考文献：
  名称：

  Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region

  摘要：

  A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P-1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P-1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P-1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.126