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9H-Carbazole Derivatives Containing the N-Benzyl-1,2,3-Triazole Moiety As New Acetylcholinesterase Inhibitors Publisher Pubmed



Akrami H1, 2 ; Mirjalili BF2 ; Khoobi M1 ; Moradi A3 ; Nadri H3 ; Emami S4 ; Foroumadi A1 ; Vosooghi M1 ; Shafiee A1
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Source: Archiv der Pharmazie Published:2015


Abstract

A series of triazole-containing carbazole derivatives were designed as new anti-acetylcholinesterase (AChE) agents. The target compounds 6a-q were simply prepared via a one-pot three-component click reaction of N-propargyl-9H-carbazole, sodium azide, and an appropriate benzyl halide. The in vitro anti-cholinesterase assay showed that the unsubstituted benzyl derivative 6p along with the 2-F, 2-Me, 3-Me, 3-MeO, and 3-F analogs (6a, 6c, and 6g-i) had significant anti-AChE activity (IC50s≤3.8μM). Among them, the 2-methylbenzyl derivative 6c with an IC50 value of 1.9μM was the most active compound. The SAR studies revealed that small halogen atoms such as the fluorine atom or electron-donating groups such as methyl or methoxy at the ortho or meta positions of the benzyl pendent group could be tolerated or improved the anti-AChE activity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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