摘要
In this work,we studied the synthesis,cytotoxicity assay,and molecular docking of hydroxychalcone derivatives as tyrosinase inhibitors.Synthesis of chalcone derivatives was carried out through a Claisen-Schmidt condensation reaction between acetophenone and benzaldehyde derivatives under alkaline conditions for 48 h.The synthesized products were characterized by using Fourier transform infrared(FTIR),gas chromatography-mass spectrometry(GC-MS),proton and carbon nuclear magnetic resonance(1H and 13C NMR)spectrometer.The in vitro inhibitory activity was evaluated against tyrosinase enzyme by employing L-3,4-dihydroxyphenylalanine(L-DOPA)as the substrate.We successfully synthesized 4-hydroxychalcone(HC)and 4-hydroxy-3-methoxychalcone(HMC)with a yield of 60%and 76%,respectively.While the tyrosinase inhibitory test of HC and HMC gave the IC50 value of 64.35 and 21.56μg/mL,respectively,demonstrating that their inhibitory activities against tyrosinase enzyme were better compared with kojic acid and hydroquinone as the positive controls.We also found that HC gave 2025μg/m L as the IC50 value against Vero cells,confirming that it was not toxic to the normal cell line.The molecular docking study gave the root-mean-square deviation value of less than 2?.Furthermore,the binding energies of hydroxychalcone derivatives were found as-30.13 and-31.38 kJ/mol,showing that those compounds could be potentially used as the alternative tyrosinase inhibitors in medical application.
