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Synthesis of New Benzimidazole-1,2,3-Triazole Hybrids As Tyrosinase Inhibitors Publisher Pubmed



Mahdavi M1 ; Ashtari A2 ; Khoshneviszadeh M3, 4 ; Ranjbar S3, 5 ; Dehghani A3, 4 ; Akbarzadeh T6, 7 ; Larijani B1 ; Khoshneviszadeh M3, 4 ; Saeedi M7, 8
Authors
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Authors Affiliations
  1. 1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, 1411713137, Iran
  2. 2. School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran
  3. 3. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, P.O. Box 71345-3388, Shiraz, Iran
  4. 4. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, P.O. Box 1583, Shiraz, 71345, Iran
  5. 5. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, P.O. Box 1583, Shiraz, 71345, Iran
  6. 6. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155, Tehran, 6451, Iran
  7. 7. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, P.O. Box 14155, Tehran, 6451, Iran
  8. 8. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155, Tehran, 6451, Iran

Source: Chemistry and Biodiversity Published:2018


Abstract

A novel series of benzimidazole-1,2,3-triazole hybrids containing substituted benzyl moieties were designed, synthesized and evaluated for their inhibitory activity against mushroom tyrosinase. The results indicated that 2-(4-{[1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}phenyl)-1H-benzimidazole (6g) and 2-(4-{[1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}phenyl)-1H-benzimidazole (6h) exhibited effective inhibitory activity with IC50 values of 9.42 and 10.34 μm, respectively, comparable to that of kojic acid as the reference drug (IC50 = 9.28 μm). Kinetic study of compound 6g confirmed mixed-type inhibitory activity towards tyrosinase indicating that it can bind to free enzyme as well as enzyme-substrate complex. Also, molecular docking analysis was performed to determine the binding mode of the most potent compounds (6g and 6h) in the active site of tyrosinase. Consequently, 6g and 6h derivatives might serve as promising candidates in cosmetics, medicine or food industry, and development of such compounds may be of an interest. © 2018 Wiley-VHCA AG, Zurich, Switzerland
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