ethyl 3-(2-oxo-3H-benzimidazol-1-yl)propanoate | 75389-55-8

• 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-(2-oxo-3H-benzimidazol-1-yl)propanoate
• CAS: 75389-55-8
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: IONLAURZPOFAQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-oxo-3H-benzimidazol-1-yl)propanoate 在 水 、 potassium carbonate 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 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：

  1-异丙烯基-2-苯并咪唑酮 在 盐酸 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 水 为溶剂， 生成 ethyl 3-(2-oxo-3H-benzimidazol-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

文献信息

• Benzimidazolone Chymase Inhibitors
  申请人：Abeywardane Asitha

  公开号：US20100240702A1

  公开（公告）日：2010-09-23

  Disclosed are small molecule inhibitors which are useful in treating various diseases and conditions involving chymase.

  公开了一种小分子抑制剂，其在治疗涉及chymase的各种疾病和病况方面是有用的。
• US9150556B2
  申请人：——

  公开号：US9150556B2

  公开（公告）日：2015-10-06
• Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region
  作者：Ho Yin Lo、Peter A. Nemoto、Jin Mi Kim、Ming-Hong Hao、Kevin C. Qian、Neil A. Farrow、Daniel R. Albaugh、Danielle M. Fowler、Richard D. Schneiderman、E. Michael August、Leslie Martin、Melissa Hill-Drzewi、Steven S. Pullen、Hidenori Takahashi、Stéphane De Lombaert

  DOI：10.1016/j.bmcl.2011.05.126

  日期：2011.8

  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.