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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
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Molecular Dermatology Research Center and Department of Dermatology, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  5. 5. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran
  6. 6. Department of Pharmacology, School of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran
  7. 7. Cardiovascular Diseases Research Center, Department of Cardiology, Heshmat Hospital, School of Medicine, Guilan University of Medical Sciences, Rasht, Iran
  8. 8. Department of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical Sciences, Shiraz, Iran
  9. 9. Student Research Committee, Shiraz University of Medical Sciences, Shiraz, Iran

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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