Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones

Abstract

To find new anti-browning and whitening agents in this study, new series of isopropylquinazolinone derivatives were designed and synthesized. All derivatives were evaluated as possible tyrosinase inhibitors and compound 9q bearing 4-fluorobenzyl moieties at the R position exhibited the best potencies with an IC50 value of 34.67 ± 3.68 µM. The kinetic evaluations of 9q as the most potent derivatives recorded mix-type inhibition. Compounds 9o and 9q also exhibited potent antioxidant capacity with IC50 values of 38.81 and 40.73 µM, respectively confirming their antioxidant potential. Molecular docking studies of 9q as the most potent derivative were exacuated and it was shown that quinazolinone and acetamide moieties of compound 9q participated in interaction with critical His residues of the binding site. The obtained results demonstrated that the 9q can be considered a suitable pharmacophore to develop potent tyrosinase inhibitors.

Structure-based development of 3,5-dihydroxybenzoyl-hydrazineylidene as tyrosinase inhibitor; in vitro and in silico study

“…The tyrosinase inhibitory activities of derivatives were performed according to the previously reported procedures 26 , 27 . All the test samples were first dissolved in DMSO at dilution to the required final concentrations.…”

Design, synthesis, and molecular dynamics simulation studies of some novel kojic acid fused 2-amino-3-cyano-4H-pyran derivatives as tyrosinase inhibitors

“…According to previously reported procedures, an induced t docking study (IFD) was performed using Maestro Molecular Modeling platform to understand the interaction mode of the most potent compound over tyrosinase enzyme with PDB ID of 2Y9X (24)(25).…”