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Yaghoub Sarrafi

Yaghoub Sarrafi

Academic rank: Professor
ORCID:
Education: PhD.
ScopusId:
Faculty: Faculty of Chemistry
Address:
Phone: 9121978350

Research

Title
Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2 (TMS-EDTA)
Type
JournalPaper
Keywords
magnetic nanoparticle catalyst, novel Thiazolone-triazole, Tyrosinase inhibitor
Year
2020
Journal APPLIED ORGANOMETALLIC CHEMISTRY
DOI
Researchers Mahdieh Darroudi ، sara ranjbar ، mohammad esfandiar ، mahsima khoshneviszadeh ، Mahshid Hamzehloueian ، mehdi khoshneviszadeh ، Yaghoub Sarrafi

Abstract

In the present work, novel 5-((1-benzyl-1,2,3-triazol-4-yl)methoxybenzylidene)- 2-(arylamino)thiazol-4-one thiazolone incorporated triazole derivatives have been designed as tyrosinase inhibitors. The compounds were synthesized through click reaction in good yield. Moreover, the antityrosinas activity of the synthesized derivatives was evaluated. In the search for establishing a click copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction under strict conditions, in terms of a novel air-stable, a recyclable and efficient magnetic catalyst was planned for new triazole derivatives as a well-organized copper iodide supported on the functionalized Fe3O4@SiO2 core-shell (CuI/Fe3O4@SiO2 (TMS-EDTA) nanoparticles). The engineered nanocatalyst synthesized for the first time and characterized by different methods, including FT-IR spectroscopy, XRD, FESEM, EDX, TEM, TGA, and BET analysis. The excellent catalytic performance in ethanol with high surface area (351.7 m2g−1) and short reaction time for diverse functional groups (120 200 min), no use of toxic solvents, reusability of the catalyst, and using eco-friendly conditions are the advantageous of this work. Moreover,the nanocatalyst can be used at least five times without any significant decrease in the yield of the reaction. The thiazolidine-triazole derivatives 9a, 9c, 9e, and 9 g showed promising tyrosinase inhibitory activity with IC50 values in the range of 5.90–9.81 μM. The compounds were found to be considerably more potent tyrosinase inhibitors than the reference inhibitor kojic acid (IC50 = 18.36 μM).