Design, Synthesis, and Antioxidant and Anti-Tyrosinase Activities of (Z)-5-Benzylidene-2-(naphthalen-1-ylamino)thiazol-4(5H)-one Analogs: In Vitro and In Vivo Insights
2025
Hee Jin Jung | Hye Jin Kim | Hyeon Seo Park | Hye Soo Park | Jeongin Ko | Dahye Yoon | Yujin Park | Pusoon Chun | Hae Young Chung | Hyung Ryong Moon
Fifteen compounds (1&ndash:15) constructed on a hybrid structure combining a &beta:-phenyl-&alpha:,&beta:-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 &mu:M) was 11 times stronger than that of kojic acid. Lineweaver&ndash: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, without cytotoxicity. Compound 15 exhibited the most potent effect on zebrafish larval depigmentation and showed a depigmentation effect comparable to kojic acid, even at a concentration 200 times lower. Compounds 8 and 10 exhibited strong antioxidant capacities, scavenging 2,2-diphenyl-1-picrylhydrazyl, (2,2-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid)+ radicals, and reactive oxygen species. Hybrid compounds 10 and 15 are potential therapeutic agents for skin hyperpigmentation disorders.
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