Design and Synthesis of (Z)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights.

ABSTRACT: Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (Z)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log p values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the ³J_C4-Hβ values of C4 measured in proton-coupled ¹³C mode. Analogs 2 (IC₅₀ = 5.21 ± 0.86 µM) and 3 (IC₅₀ = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC

SUBMITTER: Ko J 

PROVIDER: S-EPMC9598926 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature