Thiazolopyrimidine derivatives as novel class of small molecule tyrosinase inhibitor
Nastaran Ghasemi, Shahram Moradi, Aida Iraji, Mohammad Mahdavi
Abstract
Abstract Tyrosinase, the rate-limiting enzyme of melanogenesis, plays a crucial role in hyperpigmentation. As a result, in this study, a novel class of thiazolopyrimidine derivatives was developed and synthesized as tyrosinase inhibitor. The structure of derivatives was characterized using various spectroscopy techniques, including FTIR, Mass, 1 H-NMR, and 13 C-NMR. Next, the inhibitory activities of all derivatives were examined against tyrosinase, and, 6a as the most potent compound, exhibited an IC 50 value of 28.50 µM. Furthermore, the kinetic study of 6a was performed to better understand the inhibitory mechanism and its type of inhibition. The UV/Vis spectra analysis was also executed to provide valuable evidence supporting the inhibitory mechanism of compound 6a in the context of tyrosinase inhibition. Also, molecular docking and dynamic molecular study of 6a were executed to study its interactions within the enzyme’s binding site.