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Novel Tacrine-1,2,3-Triazole Hybrids: In Vitro, in Vivo Biological Evaluation and Docking Study of Cholinesterase Inhibitors Publisher Pubmed



Najafi Z1 ; Mahdavi M2 ; Saeedi M3, 4 ; Karimpourrazkenari E4 ; Asatouri R5 ; Vafadarnejad F1 ; Moghadam FH6 ; Khanavi M7 ; Sharifzadeh M8 ; Akbarzadeh T1, 4
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Department of Biology, Science and Research Branch Islamic Azad, Tehran, Iran
  6. 6. Department of Cellular Biotechnology at Cell Science Research Center, Royan Institute for Biotechnology, ACECR, Isfahan, Iran
  7. 7. Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  8. 8. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: European Journal of Medicinal Chemistry Published:2017


Abstract

A new series of tacrine-1,2,3-triazole hybrids were designed, synthesized, and evaluated as potent dual cholinesterase inhibitors. Most of synthesized compounds showed good in vitro inhibitory activities toward both acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Among them, 7-chloro-N-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-1,2,3,4-tetrahydroacridin-9-amine (5l) was found to be the most potent anti-AChE derivative (IC50= 0.521 μM) and N-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-1,2,3,4-tetrahydroacridin-9-amine (5j) demonstrated the best anti-BChE activity (IC50= 0.055 μM). In vivo studies of compound 5l in Morris water maze task confirmed memory improvement in scopolamine-induced impairment. Also, molecular modeling and kinetic studies showed that compounds 5l and 5j bound simultaneously to the peripheral anionic site (PAS) and catalytic sites (CS) of the AChE and BChE. © 2016 Elsevier Masson SAS
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