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Synthesis of Novel Chromenones Linked to 1,2,3-Triazole Ring System: Investigation of Biological Activities Against Alzheimer's Disease Publisher Pubmed



Saeedi M1, 2 ; Safavi M3 ; Karimpourrazkenari E2 ; Mahdavi M4 ; Edraki N5 ; Moghadam FH6 ; Khanavi M7 ; Akbarzadeh T2, 8
Authors
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Authors Affiliations
  1. 1. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, 3353-5111, Iran
  4. 4. Drug Design and Research Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, 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 Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2017


Abstract

In this work, novel chromenones linked to 1,2,3-triazole ring system were synthesized and evaluated for their anti-ChE activity. Among them, N-((1-(2-chlorobenzyl)-1H-1,2,3-triazol-5-yl)methyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide (6m) showed good anti-acetylcholinesterase activity (IC50 = 15.42 μM). Also, compound 6m demonstrated neuroprotective effect against H2O2-induced cell death in PC12 neurons, however, it showed no beta-secretase (BACE1) inhibitory activity. Docking and kinetic studies separately confirmed dual binding activity of compound 6m since it targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. © 2016 Elsevier Inc.
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