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Synthesis of New Benzimidazole-1,2,3-triazole Hybrids as Tyrosinase Inhibitors.
Chem Biodivers. 2018 Jul; 15(7):e1800120.CB

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.

Authors+Show Affiliations

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, 1411713137, Iran.School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran.Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, P.O. Box 71345-3388, Shiraz, Iran. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, P.O. Box 1583, 71345, Shiraz, Iran.Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, P.O. Box 71345-3388, Shiraz, Iran. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, P.O. Box 1583, 71345, Shiraz, Iran.Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, P.O. Box 71345-3388, Shiraz, Iran. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, P.O. Box 1583, 71345, Shiraz, Iran.Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155, 6451, Tehran, Iran. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, P.O. Box 14155, 6451, Tehran, Iran.Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, 1411713137, Iran.Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, P.O. Box 71345-3388, Shiraz, Iran. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, P.O. Box 1583, 71345, Shiraz, Iran.Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, P.O. Box 14155, 6451, Tehran, Iran. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155, 6451, Tehran, Iran.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29766648

Citation

Mahdavi, Mohammad, et al. "Synthesis of New Benzimidazole-1,2,3-triazole Hybrids as Tyrosinase Inhibitors." Chemistry & Biodiversity, vol. 15, no. 7, 2018, pp. e1800120.
Mahdavi M, Ashtari A, Khoshneviszadeh M, et al. Synthesis of New Benzimidazole-1,2,3-triazole Hybrids as Tyrosinase Inhibitors. Chem Biodivers. 2018;15(7):e1800120.
Mahdavi, M., Ashtari, A., Khoshneviszadeh, M., Ranjbar, S., Dehghani, A., Akbarzadeh, T., Larijani, B., Khoshneviszadeh, M., & Saeedi, M. (2018). Synthesis of New Benzimidazole-1,2,3-triazole Hybrids as Tyrosinase Inhibitors. Chemistry & Biodiversity, 15(7), e1800120. https://doi.org/10.1002/cbdv.201800120
Mahdavi M, et al. Synthesis of New Benzimidazole-1,2,3-triazole Hybrids as Tyrosinase Inhibitors. Chem Biodivers. 2018;15(7):e1800120. PubMed PMID: 29766648.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of New Benzimidazole-1,2,3-triazole Hybrids as Tyrosinase Inhibitors. AU - Mahdavi,Mohammad, AU - Ashtari,Arsalan, AU - Khoshneviszadeh,Mahsima, AU - Ranjbar,Sara, AU - Dehghani,Ameneh, AU - Akbarzadeh,Tahmineh, AU - Larijani,Bagher, AU - Khoshneviszadeh,Mehdi, AU - Saeedi,Mina, Y1 - 2018/06/21/ PY - 2018/03/18/received PY - 2018/05/04/accepted PY - 2018/5/17/pubmed PY - 2018/7/28/medline PY - 2018/5/17/entrez KW - 1,2,3-triazole KW - benzimidazole KW - click reaction KW - synthesis KW - tyrosinase inhibitor SP - e1800120 EP - e1800120 JF - Chemistry & biodiversity JO - Chem. Biodivers. VL - 15 IS - 7 N2 - 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. SN - 1612-1880 UR - https://www.unboundmedicine.com/medline/citation/29766648/Synthesis_of_New_Benzimidazole_123_triazole_Hybrids_as_Tyrosinase_Inhibitors_ L2 - https://doi.org/10.1002/cbdv.201800120 DB - PRIME DP - Unbound Medicine ER -