3-[2-Butyl-5-chloro-3-(4-nitro-benzyl)-3H-imidazol-4-yl]-propionic acid | 142219-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[2-Butyl-5-chloro-3-(4-nitro-benzyl)-3H-imidazol-4-yl]-propionic acid
• 英文别名: 3-[2-Butyl-5-chloro-3-[(4-nitrophenyl)methyl]imidazol-4-yl]propanoic acid
• CAS: 142219-31-6
• 化学式: C₁₇H₂₀ClN₃O₄
• 分子量: 365.817
• InChiKey: JAVLVHQYHFYVTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-Butyl-5-chloro-3-(4-nitro-benzyl)-3H-imidazol-4-yl]-propionic acid 在 镍 硫酸 、 氢气 作用下， 以 四氢呋喃 为溶剂， 23.0 ℃ 、344.73 kPa 条件下， 反应 2.0h， 生成 methyl 3-<(4-aminophenyl)methyl>-2-butyl-5-chloro-3H-imidazole-4-propanoate
  参考文献：
  名称：

  Nonpeptide angiotensin II receptor antagonists. 1. Synthesis and in vitro structure-activity relationships of 4-[[[(1H-pyrrol-1-ylacetyl)amino]phenyl]methyl]imidazole derivatives as angiotensin II receptor antagonists

  摘要：

  A novel series of non-biphenylyltetrazole angiotensin II receptor antagonists which contain a 1H-pyrrol-1-ylacetyl residue in place of the benzoyl residue in EXP 6803 have been developed. The receptor binding activity of several members of this new series was in the 10(-8) M range, which was better than that of EXP 6803. Introduction of a carboxylic acid moiety at the 2-position of the pyrrole ring enhanced the in vitro binding affinity at the receptor by 10-fold. Compounds containing an acetic acid (18) or a propionic acid residue (20) at the 5-position of the imidazole were more potent than the carboxylic acid analogue (24). The binding IC50 of the most potent compound 20 was 22 nM. Compounds 18, 20, and 24 in their best fit conformations were manually overlayed on that of the template conformation of EXP 6803 and EXP 8623, respectively. The synthesis and structure-activity relationship data are described.

  DOI：

  10.1021/jm00064a007
• 作为产物：
  描述：

  对硝基溴化苄 在 盐酸 、 磺酰氯 、 sodium hydride 作用下， 反应 24.5h， 生成 3-[2-Butyl-5-chloro-3-(4-nitro-benzyl)-3H-imidazol-4-yl]-propionic acid
  参考文献：
  名称：

  Nonpeptide angiotensin II receptor antagonists. 1. Synthesis and in vitro structure-activity relationships of 4-[[[(1H-pyrrol-1-ylacetyl)amino]phenyl]methyl]imidazole derivatives as angiotensin II receptor antagonists

  摘要：

  A novel series of non-biphenylyltetrazole angiotensin II receptor antagonists which contain a 1H-pyrrol-1-ylacetyl residue in place of the benzoyl residue in EXP 6803 have been developed. The receptor binding activity of several members of this new series was in the 10(-8) M range, which was better than that of EXP 6803. Introduction of a carboxylic acid moiety at the 2-position of the pyrrole ring enhanced the in vitro binding affinity at the receptor by 10-fold. Compounds containing an acetic acid (18) or a propionic acid residue (20) at the 5-position of the imidazole were more potent than the carboxylic acid analogue (24). The binding IC50 of the most potent compound 20 was 22 nM. Compounds 18, 20, and 24 in their best fit conformations were manually overlayed on that of the template conformation of EXP 6803 and EXP 8623, respectively. The synthesis and structure-activity relationship data are described.

  DOI：

  10.1021/jm00064a007

文献信息

• Angiotensin II receptor blocking imidazoles
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0253310A2

  公开（公告）日：1988-01-20

  Substituted imidazoles such as are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.

  这些化合物具有治疗高血压和充血性心力衰竭的活性。
• Angiotensin II receptor blocking imidazoles and combinations thereof with diuretics and NSaids
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0324377A2

  公开（公告）日：1989-07-19

  The invention encompasses a pharmaceutical composition comprising a diuretic or a non-steroidal antiinflammatory drug, a pharmaceutical suitable carrier and an antihypertensive and processes for production of these compositions.

  本发明包括一种由利尿剂或非类固醇抗炎药物、适合制药的载体和降压药组成的药物组合物，以及生产这些组合物的工艺。
• Pharmaceutical compositions comprising angiotensin II receptor blocking imidazoles and diuretics
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0733366A2

  公开（公告）日：1996-09-25

  The invention encompasses a pharmaceutical composition comprising a diuretic or a non-steroidal antiinflammatory drug, a pharmaceutical suitable carrier and an antihypertensive and processes for production of these compositions.

  本发明包括一种由利尿剂或非类固醇抗炎药物、适合制药的载体和降压药组成的药物组合物，以及生产这些组合物的工艺。
• US5128355A
  申请人：——

  公开号：US5128355A

  公开（公告）日：1992-07-07
• US5138069A
  申请人：——

  公开号：US5138069A

  公开（公告）日：1992-08-11