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Benzofuran-Derived Benzylpyridinium Bromides As Potent Acetylcholinesterase Inhibitors Publisher Pubmed



Baharloo F1 ; Moslemin MH1 ; Nadri H2 ; Asadipour A3 ; Mahdavi M4 ; Emami S5 ; Firoozpour L6 ; Mohebat R1 ; Shafiee A4 ; Foroumadi A3, 4
Authors

Source: European Journal of Medicinal Chemistry Published:2015


Abstract

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. © 2015 Elsevier Masson SAS.
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