N-(3-bromobenzyl)-4-(7-methoxybenzofuran-2-yl)pyridinium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-(3-bromobenzyl)-4-(7-methoxybenzofuran-2-yl)pyridinium bromide
• 英文别名: 1-[(3-Bromophenyl)methyl]-4-(7-methoxy-1-benzofuran-2-yl)pyridin-1-ium;bromide；1-[(3-bromophenyl)methyl]-4-(7-methoxy-1-benzofuran-2-yl)pyridin-1-ium;bromide
• 化学式: Br*C₂₁H₁₇BrNO₂
• 分子量: 475.179
• InChiKey: AJOIOXVURWFQFZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴甲基吡啶 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 N-(3-bromobenzyl)-4-(7-methoxybenzofuran-2-yl)pyridinium bromide
  参考文献：
  名称：

  Benzofuran-derived benzylpyridinium bromides as potent acetylcholinesterase inhibitors

  摘要：

  A series of benzofuran-based N-benzylpyridinium derivatives 5a-o were designed and synthesized as novel AChE inhibitors. The synthetic pathway of the compounds involved the preparation of 4-(benzofuran-2-yl)pyridine intermediates via the reaction of different salicylaldehyde derivatives and 4-(bromomethyl)pyridine, followed by intramolecular cyclization. Subsequently, the 4-(benzofuran-2-yl) pyridines were N-benzylated by using appropriate benzyl bromide to afford the final product 5a-o. The results of in vitro AChE activity evaluation of synthesized compounds revealed that all compound had potent anti-AChE activity comparable or more potent than standard drug donepezil. The N-(3,5-dimethylbenzyl) derivative 5e with IC50 value of 4.1 nM was the most active compound, being 7-fold more potent than donepezil. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.009

文献信息

• Benzofuran-derived benzylpyridinium bromides as potent acetylcholinesterase inhibitors
  作者：Farzaneh Baharloo、Mohammad Hossein Moslemin、Hamid Nadri、Ali Asadipour、Mohammad Mahdavi、Saeed Emami、Loghman Firoozpour、Razieh Mohebat、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2015.02.009

  日期：2015.3

  A series of benzofuran-based N-benzylpyridinium derivatives 5a-o were designed and synthesized as novel AChE inhibitors. The synthetic pathway of the compounds involved the preparation of 4-(benzofuran-2-yl)pyridine intermediates via the reaction of different salicylaldehyde derivatives and 4-(bromomethyl)pyridine, followed by intramolecular cyclization. Subsequently, the 4-(benzofuran-2-yl) pyridines were N-benzylated by using appropriate benzyl bromide to afford the final product 5a-o. The results of in vitro AChE activity evaluation of synthesized compounds revealed that all compound had potent anti-AChE activity comparable or more potent than standard drug donepezil. The N-(3,5-dimethylbenzyl) derivative 5e with IC50 value of 4.1 nM was the most active compound, being 7-fold more potent than donepezil. (C) 2015 Elsevier Masson SAS. All rights reserved.