2-butyl-4-methyl-1-<(4-nitrophenyl)methyl>-1H-benzimidazole | 142219-33-8

• 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: 2-butyl-4-methyl-1-<(4-nitrophenyl)methyl>-1H-benzimidazole
• 英文别名: 2-Butyl 4-methyl-1-[(4-nitrophenyl)methyl]-1H-benzimidazole；2-butyl-4-methyl-1-[(4-nitrophenyl)methyl]benzimidazole
• CAS: 142219-33-8
• 化学式: C₁₉H₂₁N₃O₂
• 分子量: 323.395
• InChiKey: YEEPWBUNFSILOP-UHFFFAOYSA-N

物化性质

• 沸点：
  537.9±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-butyl-4-methyl-1-<(4-nitrophenyl)methyl>-1H-benzimidazole 在 镍 4-二甲氨基吡啶 、 氢气 、 三甲基乙酰氯 作用下， 以 四氢呋喃 为溶剂， 23.0 ℃ 、344.73 kPa 条件下， 生成 (S) Methyl 1-[2-[[4-[(2-butyl-4-methyl-1H-benzimidazol-1-yl)methyl]phenyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-1H-pyrrole-2-carboxylate
  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-甲基-1H-苯并咪唑 、 对硝基溴化苄 在 NaH 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-butyl-4-methyl-1-<(4-nitrophenyl)methyl>-1H-benzimidazole
  参考文献：
  名称：

  Anilide derivatives with angiotensin II antagonist properties

  摘要：

  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。

  公开号：

  US05242939A1

文献信息

• 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。
• [EN] ANILIDE DERIVATIVES WITH ANGIOTENSIN II ANTAGONIST PROPERTIES
  申请人：——

  公开号：WO1992006081A1

  公开（公告）日：1992-04-16

  [FR] La présente invention concerne de nouveaux dérivés d'anilide de formule (I) qui inhibent la fixation de l'angiotensine II sur ses récepteurs. Ces composés sont utiles dans le traitement de l'hypertension, de l'insuffisance cardiaque, du glaucome et de l'hyperaldostéronisme. Sont également décrits des procédés pour fabriquer les composés, de nouveaux intermédiaires utiles dans la préparation de ces composés, des compositions les renfermant et des procédés pour les utiliser.
  [EN] This invention relates to novel anilide derivatives of formula (I) 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.
• 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
  作者：Ila Sircar、R. Thomas Winters、John Quin、Gina H. Lu、Terry C. Major、Robert L. Panek

  DOI：10.1021/jm00064a007

  日期：1993.6

  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.