ethyl 3-(3-((5-chloro-1,2,3-trimethyl-1H-indol-7-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propanoate | 1325147-82-7

• 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: ethyl 3-(3-((5-chloro-1,2,3-trimethyl-1H-indol-7-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propanoate
• CAS: 1325147-82-7
• 化学式: C₂₄H₂₆ClN₃O₃
• 分子量: 439.942
• InChiKey: REPISBPUUVXCBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.16
• 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-((5-chloro-1,2,3-trimethyl-1H-indol-7-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90%的产率得到3-{3-[(5-chloro-1,2,3-trimethyl-1H-indol-7-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：

  5-氯-2-硝基苯甲醛 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 ethyl 3-(3-((5-chloro-1,2,3-trimethyl-1H-indol-7-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