1-[(4-Aminophenyl)methyl]-2-butyl-4-chloro-1H-imidazole-5-methanol | 114772-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[(4-Aminophenyl)methyl]-2-butyl-4-chloro-1H-imidazole-5-methanol
• 英文别名: 1-<4-(aminophenyl)methyl>-2-butyl-4-chloro-1H-imidazole-5-methanol；1-(4-Aminobenzyl)-2-butyl-4-chloro-5-(hydroxymethyl)imidazole；[3-[(4-Aminophenyl)methyl]-2-butyl-5-chloroimidazol-4-yl]methanol
• CAS: 114772-08-6
• 化学式: C₁₅H₂₀ClN₃O
• 分子量: 293.796
• InChiKey: MEWHXPHXPBQNIO-UHFFFAOYSA-N

物化性质

• 沸点：
  501.6±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4-Aminophenyl)methyl]-2-butyl-4-chloro-1H-imidazole-5-methanol 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 (S)-2-{2-[4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-ylmethyl)-phenylcarbamoyl]-pyrrol-1-yl}-3-phenyl-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
• 作为产物：
  描述：

  2-丁基-4-氯-1-[(4-硝基苯基)甲基]-1H-咪唑-5-甲醇 在 aluminum nickel 作用下， 以 四氢呋喃 为溶剂， 生成 1-[(4-Aminophenyl)methyl]-2-butyl-4-chloro-1H-imidazole-5-methanol
  参考文献：
  名称：

  Amino acid derivatives with angiotensin II antagonist properties

  摘要：

  这项发明涉及新型氨基酸衍生物，其拮抗血管紧张素II与其受体的结合。这些化合物在治疗高血压、心力衰竭、青光眼和高醛固酮症方面具有用途。制备这些化合物的方法，用于分离这些化合物的新型中间体，含有这些化合物的组合物以及使用它们的方法也被涵盖。

  公开号：

  US05041552A1

文献信息

• Angiotensin II receptor blocking imidazoles
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05138069A1

  公开（公告）日：1992-08-11

  Substituted imidazoles such as ##STR1## are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.

  取代咪唑类化合物如##STR1##可作为抗血管紧张素II受体拮抗剂。这些化合物在治疗高血压和充血性心力衰竭方面具有活性。
• Treatment of congestive heart failure with angiotensin 11 receptor
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05128355A1

  公开（公告）日：1992-07-07

  Substituted imidazoles such as ##STR1## are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.

  取代咪唑类化合物如##STR1##对抗高血压和充血性心力衰竭有一定的活性。
• Amino acid derivatives with angiotensin II antagonist properties
  申请人：Warner-Lambert Company

  公开号：US05041552A1

  公开（公告）日：1991-08-20

  This invention relates to novel amino acid derivatives which antagonize the binding of angiotensin II to its receptors. The compounds are useful in the treatment of hypertension, heart failure, glaucoma, and hyperaldosteronism. Methods of making the compounds, novel intermediates useful in the separation of the compounds, compositions containing the compounds and methods of using them are also covered.

  这项发明涉及新型氨基酸衍生物，其拮抗血管紧张素II与其受体的结合。这些化合物在治疗高血压、心力衰竭、青光眼和高醛固酮症方面具有用途。制备这些化合物的方法，用于分离这些化合物的新型中间体，含有这些化合物的组合物以及使用它们的方法也被涵盖。
• Anilide derivatives with angiotensin II antagonist properties
  申请人：Warner-Lambert Company

  公开号：US05242939A1

  公开（公告）日：1993-09-07

  This invention relates to anilide derivatives of Formula I ##STR1## which antagonize the binding of angiotensin II to its receptors. The compounds are useful in the treatment of hypertension, heart failure, glaucoma, and hyperaldosteronism. Methods of making the compounds, novel intermediates useful in the preparation of the compounds, compositions containing the compounds and methods of using them are also covered.

  这项发明涉及公式I的苯酰胺衍生物，其对抗血管紧张素II与其受体的结合。这些化合物在治疗高血压、心力衰竭、青光眼和高醛固酮血症方面具有用途。制备这些化合物的方法，制备这些化合物的新型中间体，含有这些化合物的组合物以及使用它们的方法也涵盖在内。
• 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。