School of Chemistry, College of Science, University of Tehran, Tehran, Iran.
School of Chemistry, College of Science, University of Tehran, Tehran, Iran.
Bioorg Chem. 2018 Oct;80:180-188. doi: 10.1016/j.bioorg.2018.06.006. Epub 2018 Jun 6.
A series of benzofuran-2-carboxamide-N-benzyl pyridinium halide derivatives (6a-o) are synthesized as new cholinesterase inhibitors. The synthetic pathway involves the reaction of salicylaldehyde derivatives and ethyl bromoacetate, followed by hydrolysis and amidation with 3- and 4-picolyl amine. Subsequently, N-((pyridin-4-yl) methyl) benzofuran-2-carboxamide and substituted N-((pyridin-3-yl) methyl) benzofuran-2-carboxamides reacts with benzyl halides to afford target compounds (6a-o). The chemical structures of all derivatives were confirmed by spectroscopic methods. The studies reveal that some of the synthesized compounds are potent butyrylcholinesterase inhibitors with IC values in the range of 0.054-2.7 µM. In addition, good inhibitory effects on Aβ self-aggregation are observed for 6h and 6k (33.1 and 46.4% at 100 µM, respectively).
一系列苯并呋喃-2-甲酰胺-N-苄基吡啶卤代物衍生物（6a-o）被合成作为新的胆碱酯酶抑制剂。合成途径包括水杨醛衍生物与溴代乙酸乙酯的反应，然后与 3-和 4-吡啶甲胺进行水解和酰胺化。随后，N-((吡啶-4-基)甲基)苯并呋喃-2-甲酰胺和取代的 N-((吡啶-3-基)甲基)苯并呋喃-2-甲酰胺与苄基卤化物反应得到目标化合物（6a-o）。所有衍生物的化学结构均通过光谱方法确认。研究表明，一些合成的化合物是有效的丁酰胆碱酯酶抑制剂，IC 值在 0.054-2.7 µM 范围内。此外，在 100 µM 时，化合物 6h 和 6k 对 Aβ 自聚集具有良好的抑制作用（分别为 33.1%和 46.4%）。
