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Evaluating the Effects of Disubstituted 3-Hydroxy-1H-Pyrrol-2(5H)-One Analog As Novel Tyrosinase Inhibitors Publisher Pubmed



Alizadeh N7 ; Hossein Sayahi M2 ; Iraji A3, 4 ; Yazzaf R7 ; Moazzam A1 ; Mobaraki K5 ; Adib M7 ; Attarroshan M6 ; Larijani B1 ; Rastegar H8 ; Khoshneviszadeh M5, 6 ; Mahdavi M1
Authors
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Authors Affiliations
  1. 1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Chemistry, Payam Noor University, Tehran, Iran
  3. 3. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran
  5. 5. Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
  6. 6. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  7. 7. School of Chemistry, College of Science, University of Tehran, Tehran, PO Box, 14155-6455, Iran
  8. 8. Cosmetic Products Research Center, Iranian Food and Drug Administration, Tehran, MOHE, Iran

Source: Bioorganic Chemistry Published:2022


Abstract

In the present study, a series of 3-hydroxy-1H-pyrrol-2(5H)-one derivative were rationally designed and synthesized. The structure of targeted compounds was confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. Next, all derivatives were evaluated as tyrosinase inhibitors, and among the synthesized derivatives, compound 6a was proved to be the most potent inhibitor with an IC50 value of 6.98 ± 1.05 µM. Kinetic study of compound 6a confirmed the mixed type of inhibitory activity towards tyrosinase. Furthermore, the results of the molecular docking study showed that this compound fitted well in the active site of tyrosinase and exhibited interaction with important residues of the binding site. © 2022
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