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Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis Publisher



Tehrani MB1 ; Emani P1 ; Rezaei Z1 ; Khoshneviszadeh M2 ; Ebrahimi M3 ; Edraki N2 ; Mahdavi M4 ; Larijani B4 ; Ranjbar S5 ; Foroumadi A1 ; Khoshneviszadeh M2
Authors

Source: Journal of Molecular Structure Published:2019


Abstract

A novel series of phthalimide-1,2,3-trizole hybrids linked to benzyl ring containing different substituents were synthesized and evaluated for their tyrosinase inhibitory activity (inhibitory activity and inhibition kinetic). It was found that compounds 2-((1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl)isoindoline-1,3-dione (6m) and 2-((1-(2-bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl)isoindoline-1,3-dione (6k), exhibited the best tyrosinase inhibitory activity, with IC50 values of 26.20 ± 1.55 and 26.55 ± 2.31 μM, respectively. The inhibition kinetic analysis of 6m indicated that the compound inhibited tyrosinase in a competitive manner. Moreover, molecular docking analysis was performed to study the interactions and binding modes of the tested compounds. Docking results confirmed that the active inhibitors well accumulated in the mushroom tyrosinase active site. © 2018
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