Design, Synthesis, and Antioxidant and Anti-Tyrosinase Activities of (<i>Z</i>)-5-Benzylidene-2-(naphthalen-1-ylamino)thiazol-4(5<i>H</i>)-one Analogs: In Vitro and In Vivo Insights.

ABSTRACT: Fifteen compounds (1-15) constructed on a hybrid structure combining a β-phenyl-α,β-unsaturated carbonyl template and a 2-aminothiazol-4(5H)-one scaffold were designed and synthesized as potential novel anti-tyrosinase substances. Two compounds (10 and 15) showed more potent inhibition against mushroom tyrosinase than kojic acid, and the inhibitory activity of 10 (IC₅₀ value: 1.60 μM) was 11 times stronger than that of kojic acid. Lineweaver-Burk plots indicated that these two compounds were competitive inhibitors that bound to the mushroom tyrosinase active site, which was supported by in silico experiments. Compound 10 was an anti-tyrosinase and anti-melanogenic substance in B16F10 cells and was more potent than kojic acid, with

SUBMITTER: Jung HJ 

PROVIDER: S-EPMC11767423 | biostudies-literature | 2025 Jan

REPOSITORIES: biostudies-literature