4-(1H-benzo[d]imidazol-2-yl)-1-benzylpyridinium bromide | 51784-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-(1H-benzo[d]imidazol-2-yl)-1-benzylpyridinium bromide
• 英文别名: 2-(1-benzylpyridin-1-ium-4-yl)-1H-benzimidazole;bromide
• CAS: 51784-48-6
• 化学式: Br*C₁₉H₁₆N₃
• 分子量: 366.26
• InChiKey: WXWWFHUPNDIEIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1H-benzo[d]imidazol-2-yl)-1-benzylpyridinium bromide 在 甲醇 、 sodium tetrahydroborate 、 1-氯乙基氯甲酸酯 作用下， 以 乙醇 为溶剂， 生成 2-(1,2,3,6-Tetrahydro-pyridin-4-yl)-1H-benzoimidazole
  参考文献：
  名称：

  4-Heterocyclyl tetrahydropyridines as selective ligands for the human dopamine D4 receptor

  摘要：

  A series of 1,2,3,6-tetrahydropyridines 3 were synthesised, which resulted in selective high affinity dopamine Dq ligands. The SAR of heterocyclic replacements and aromatic substitution was investigated, leading to compounds of nanomolar binding affinity with excellent selectivity over both D-2 and D-3 receptors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00402-2
• 作为产物：
  描述：

  异烟酸 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(1H-benzo[d]imidazol-2-yl)-1-benzylpyridinium bromide
  参考文献：
  名称：

  4-Heterocyclyl tetrahydropyridines as selective ligands for the human dopamine D4 receptor

  摘要：

  A series of 1,2,3,6-tetrahydropyridines 3 were synthesised, which resulted in selective high affinity dopamine Dq ligands. The SAR of heterocyclic replacements and aromatic substitution was investigated, leading to compounds of nanomolar binding affinity with excellent selectivity over both D-2 and D-3 receptors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00402-2

文献信息

• Synthesis and biological evaluation of new N-benzylpyridinium-based benzoheterocycles as potential anti-Alzheimer’s agents
  作者：Naeimeh Salehi、Bi Bi Fatemeh Mirjalili、Hamid Nadri、Zahra Abdolahi、Hamid Forootanfar、Alireza Samzadeh-Kermani、Tuba Tüylü Küçükkılınç、Beyza Ayazgok、Saeed Emami、Ismaeil Haririan、Mohammad Sharifzadeh、Alireza Foroumadi、Mehdi Khoobi

  DOI：10.1016/j.bioorg.2018.11.010

  日期：2019.3

  A novel series of benzylpyridinium-based benzoheterocycles (benzimidazole, benzoxazole or benzothiazole) were designed as potent acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The title compounds 4a-q were conveniently synthesized via condensation reaction of 1,2-phenylenediamine, 2-amino-phenol or 2-aminothiophenol with pyridin-4-carbalehyde, followed by N-benzylation using various benzyl halides. The results of in vitro biological assays revealed that most of them, especially 4c and 4g, had potent anticholinesterase activity comparable or more potent than reference drug, donepezil. The kinetic study demonstrated that the representative compound 4c inhibits AChE in competitive manner. According to the ligand-enzyme docking simulation, compound 4c occupied the active site at the vicinity of catalytic triad. The compounds 4c and 4g were found to be inhibitors of A beta self-aggregation as well as AChE-induced A beta aggregation. Meanwhile, these compounds could significantly protect PC12 cells against H2O2-induced injury and showed no toxicity against HepG2 cells. As multi-targeted structures, compounds 4c and 4g could be considered as promising candidate for further lead developments to treat Alzheimer's disease.