1-((piperidin-1-yl) methyl)-2-styryl-benzimidazole | 1154461-62-7

• 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: 1-((piperidin-1-yl) methyl)-2-styryl-benzimidazole
• 英文别名: 2-(2-Phenylethenyl)-1-(piperidin-1-ylmethyl)benzimidazole；2-(2-phenylethenyl)-1-(piperidin-1-ylmethyl)benzimidazole
• CAS: 1154461-62-7
• 化学式: C₂₁H₂₃N₃
• 分子量: 317.434
• InChiKey: BHVPZXDBQYXXEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哌啶 、 聚合甲醛 、 2-styryl-1H-benzo[d]imidazole 以 乙醇 为溶剂， 反应 0.75h， 以78%的产率得到1-((piperidin-1-yl) methyl)-2-styryl-benzimidazole
  参考文献：
  名称：

  Synthesis, pharmacological screening, quantum chemical and in vitro permeability studies of N-Mannich bases of benzimidazoles through bovine cornea

  摘要：

  A novel series of N-Mannich bases of benzimidazole derivatives were synthesized and characterized by H-1 NMR, IR spectral studies and elemental analysis. The compounds were screened for analgesic and anti-inflammatory activity. 1-((Diethylamino)-methyl)-2-styryl benzimidazole 4 at 40 mg/kg was found to be equipotent to paracetamol. 1-((Piperidin-1-yl) methyl)-2-styryl-benzimidazole 6 at 40 mg/kg was found to be more potent than Diclofenac. Corneal permeability and quantum chemical calculations were performed to correlate the hydrogen bonding ability with permeability and activity. The energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) were correlated with pharmacological activity. The semi-empirical PM3 calculations (quantum chemical calculations) revealed that E-LUMO and energy gap Delta E were capable of accounting for the high in vitro bovine corneal permeability and activity of the compounds. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.043