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Synthesis and Tyrosinase Inhibitory Activities of Novel Isopropylquinazolinones Publisher



Hashemi A1 ; Noori M2, 4 ; Dastyafteh N2 ; Sadatebrahimi SE1 ; Fazelzadeh Haghighi N3 ; Mehrpour K4, 5 ; Sattarinezhad E6 ; Jalali Zafrei F7 ; Irajie C8 ; Daneshmehr MA1 ; Heydari M9 ; Larijani B2 ; Iraji A4, 5 ; Mahdavi M2
Authors

Source: BMC Chemistry Published:2023


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. © 2023, The Author(s).
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