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Synthesis and Anticholinergic Activity of 4-Hydroxycoumarin Derivatives Containing Substituted Benzyl-1,2,3-Triazole Moiety Publisher Pubmed



Bagheri SM1, 2 ; Khoobi M1 ; Nadri H3 ; Moradi A3 ; Emami S4 ; Jalilibaleh L1 ; Jafarpour F2 ; Homayouni Moghadam F5 ; Foroumadi A1 ; Shafiee A1
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, 14176, Iran
  2. 2. School of Chemistry, College of Science University of Tehran, PO Box 14155-6455, Tehran, Iran
  3. 3. Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
  4. 4. Department of Medicinal Chemistry, Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran
  5. 5. Neurobiomedical Research Center, School of Medicine, Shahid Sadoughi University of Medical Sciences, Yazd, Iran

Source: Chemical Biology and Drug Design Published:2015


Abstract

A series of 4-hydroxycoumarin-derived compounds 8a-p containing N-benzyl-1,2,3-triazole motif were designed as AChE inhibitors. The title compounds were obtained conveniently using multicomponent click reaction. The in vitro anticholinesterase evaluation of synthesized compounds against AChE and BuChE showed that some of them are potent and selective inhibitors of AChE. Among them, 2-chlorobenzyl derivative 8k showed the most potent activity against AChE (IC50 = 0.18 μm). Its activity was also superior to that of standard drug tacrine. The kinetic study and molecular docking simulation of the most potent compound 8k were also described. A series of 4-hydroxycoumarin derivatives 8a-p containing N-benzyl-1,2,3-triazole motif were designed and synthesized as AChE inhibitors. Among them, 2-chlorobenzyl derivative 8k showed the most potent activity against AChE (IC50 = 0.18 μm). © 2015 John Wiley & Sons A/S.
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