Identification of (Z)-2-benzylidene-dihydroimidazothiazolone derivatives as tyrosinase inhibitors: Anti-melanogenic effects and in silico studies.

ABSTRACT: As part of our continuous search for novel tyrosinase inhibitors, we designed 5,6-dihydroimindazo[2,1-b]thiazol-3(2H)-one (DHIT) derivatives based on the structure of MHY773; a potent tyrosinase inhibitor with a 2-iminothiazolidin-4-one template. Of the 11 DHIT derivatives synthesized using a Knoevenagel condensation, three DHIT derivatives 1a (IC₅₀ = 36.14 ± 3.90 μM), 1b (IC₅₀ = 0.88 ± 0.91 μM), and 1f (IC₅₀ = 17.10 ± 1.01 μM) inhibited mushroom tyrosinase more than kojic acid (IC₅₀ = 84.41 ± 2.87 μM). Notably, compound 1b inhibited mushroom tyrosinase around 100- and 3.3-fold more potently than kojic acid and MHY773, respectively. Lineweaver-Burk plots demonstrated that compounds 1b and 1f

SUBMITTER: Choi H 

PROVIDER: S-EPMC8861568 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature