2H-Benzimidazol-2-one, 1,3-dihydro-1-(1-methyl-1-propenyl)- | 178042-32-5

• 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: 2H-Benzimidazol-2-one, 1,3-dihydro-1-(1-methyl-1-propenyl)-
• 英文别名: 3-but-2-en-2-yl-1H-benzimidazol-2-one
• CAS: 178042-32-5
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: JPPUGGIGITVSIA-UHFFFAOYSA-N

物化性质

• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2H-Benzimidazol-2-one, 1,3-dihydro-1-(1-methyl-1-propenyl)- 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-(3,4-Dichloro-phenyl)-N-(1-{2-[3-((E)-1-methyl-propenyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-ethyl}-piperidin-4-yl)-propionamide
  参考文献：
  名称：

  Pharmacological profile of a novel series of NK1 antagonists. In vitro and in vivo potency of benzimidazolone derivatives

  摘要：

  By low throughput examination of our chemical library, compound 7 was selected as a lead NK, antagonist with a K-i of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.

  DOI：

  10.1016/s0223-5234(97)82771-7
• 作为产物：
  描述：

  邻苯二胺 、 丙酰乙酸乙酯 在 氢氧化钾 作用下， 以 水 、 xylene 为溶剂， 生成 2H-Benzimidazol-2-one, 1,3-dihydro-1-(1-methyl-1-propenyl)- 、 1-(1-丁烯-2-基)-1,3-二氢-2H-苯并咪唑-2-酮
  参考文献：
  名称：

  Pharmacological profile of a novel series of NK1 antagonists. In vitro and in vivo potency of benzimidazolone derivatives

  摘要：

  By low throughput examination of our chemical library, compound 7 was selected as a lead NK, antagonist with a K-i of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.

  DOI：

  10.1016/s0223-5234(97)82771-7