Design, Synthesis, and Anti-Tyrosinase, Anti-Melanogenic, and Antioxidant Activities of Novel <i>(Z)</i>-3-Benzyl-5-Benzylidene-2-Thioxothiazolidin-4-One Analogs.

ABSTRACT: To discover novel anti-melanogenic compounds with tyrosinase inhibitory activity, (Z)-3-benzyl-5-benzylidene-2-thioxothiazolidin-4-one ((Z)-BBTT) analogs 1-12, designed based on the hybrid structure of a β-phenyl-α,β-unsaturated carbonyl motif and a 3-benzyl-2-thioxothiazolidin-4-one scaffold, were synthesized as novel tyrosinase inhibitors. Of the 12 analogs, 2 (6 and 8) showed mushroom tyrosinase inhibitory activity similar to that of kojic acid, a representative tyrosinase inhibitor, and 3 analogs (1-3) exhibited mushroom tyrosinase inhibitory activity that was more potent than that of kojic acid. In particular, analog 3 revealed highly potent inhibition with an IC₅₀ value of 90 nM, which was 214 times lower than

SUBMITTER: Park HS 

PROVIDER: S-EPMC11820736 | biostudies-literature | 2025 Jan

REPOSITORIES: biostudies-literature