Microwave‐assisted synthesis and biological evaluation of new thiazolylhydrazone derivatives as tyrosinase inhibitors and antioxidants. (27th January 2020)

• Record Type: Journal Article
• Authors: Zhang, Yu; Fu, Xi; Yan, Yangting; Liu, Jinbing
• Is Part Of: Journal of heterocyclic chemistry. Volume 57:Number 3(2020)
• Page Start: 991
• Page End: 1002
• Publication Date: 2020-01-27
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.3760
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract: In this work, we have synthesized a series of 2‐thiazolylhydrazone derivatives (1–27 ) and investigated their biological activities as tyrosinase inhibitors and antioxidants. Some compounds showed potent tyrosinase inhibitory activities and 4‐(2‐(2‐(1‐(4‐Aminophenyl)ethylidene)‐hydrazinyl)thiazol‐4‐yl) phenol (26 ) showed more potent inhibitory effect than the standard tyrosinase inhibitor kojic acid (IC50 : 9.8 μM vs. 23.6 μM). Compounds 2, 14, and 26 exhibited high antioxidant activities in 2, 2‐diphenyl‐1‐picrylhydrazyl (DPPH) and 2, 2′‐azinobis (3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS) assays. The structure–activity relationship (SAR) indicated that the substitutions of bromine, hydroxyl group, and amino groups cause great effect to the inhibition effect against tyrosinase. The mechanism and kinetic studies demonstrated that the inhibitory effect of compound 26 on the tyrosinase by acting as the reversible and uncompetitive inhibitor. Docking studies suggests that compound 26 interacts strongly with mushroom tyrosinase via hydrogen bonding. Abstract :