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

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

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
2. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
3. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
5. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

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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Mohammad Mahdavi (7)

Bagher Larijani (4)

Style	Citing Format
MLA	Tehrani MB, et al.. "Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis." Journal of Molecular Structure, vol. 1176, no. , 2019, pp. 86-93.
APA	Tehrani MB, Emani P, Rezaei Z, Khoshneviszadeh M, Ebrahimi M, Edraki N, Mahdavi M, Larijani B, Ranjbar S, Foroumadi A, Khoshneviszadeh M (2019). Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis. Journal of Molecular Structure, 1176(), 86-93.
Chicago	Tehrani MB, Emani P, Rezaei Z, Khoshneviszadeh M, Ebrahimi M, Edraki N, Mahdavi M, et al.. "Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis." Journal of Molecular Structure 1176, no. (2019): 86-93.
Harvard	Tehrani MB et al. (2019) 'Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis', Journal of Molecular Structure, 1176(), pp. 86-93.
Vancouver	Tehrani MB, Emani P, Rezaei Z, Khoshneviszadeh M, Ebrahimi M, Edraki N, et al.. Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis. Journal of Molecular Structure. 2019;1176():86-93.
BibTex	@article{ author = {Tehrani MB and Emani P and Rezaei Z and Khoshneviszadeh M and Ebrahimi M and Edraki N and Mahdavi M and Larijani B and Ranjbar S and Foroumadi A and Khoshneviszadeh M}, title = {Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis}, journal = {Journal of Molecular Structure}, volume = {1176}, number = {}, pages = {86-93}, year = {2019} }
RIS	TY - JOUR AU - Tehrani MB AU - Emani P AU - Rezaei Z AU - Khoshneviszadeh M AU - Ebrahimi M AU - Edraki N AU - Mahdavi M AU - Larijani B AU - Ranjbar S AU - Foroumadi A AU - Khoshneviszadeh M TI - Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis JO - Journal of Molecular Structure VL - 1176 IS - SP - 86 EP - 93 PY - 2019 ER -

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