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Design, Synthesis, Biological Evaluation, and Molecular Docking Study of Thioxo-2,3-Dihydroquinazolinone Derivative As Tyrosinase Inhibitors Publisher



Sepehri N1 ; Khoshneviszadeh M2, 3 ; Farid SM4 ; Moayedi SS2 ; Asgari MS5 ; Moazzam A4 ; Hosseini S6 ; Adibi H4 ; Larijani B4 ; Pirhadi S3 ; Attarroshan M3 ; Sakhteman A2 ; Kabiri M2 ; Hamedifar H7 Show All Authors
Authors
  1. Sepehri N1
  2. Khoshneviszadeh M2, 3
  3. Farid SM4
  4. Moayedi SS2
  5. Asgari MS5
  6. Moazzam A4
  7. Hosseini S6
  8. Adibi H4
  9. Larijani B4
  10. Pirhadi S3
  11. Attarroshan M3
  12. Sakhteman A2
  13. Kabiri M2
  14. Hamedifar H7
  15. Iraji A8, 9
  16. Mahdavi M4
Show Affiliations
Authors Affiliations
  1. 1. Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
  3. 3. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  6. 6. Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
  7. 7. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  8. 8. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  9. 9. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran

Source: Journal of Molecular Structure Published:2022


Abstract

Tyrosinase is known to be a key enzyme in melanogenesis and hyperpigmentation. In this study, a series of thioxo-dihydroquinazolinone compounds were designed and synthesized as tyrosinase inhibitors. Among the investigated compounds, 4m demonstrated the best inhibitory activity with an IC50 value of 15.48 µM compared to kojic acid as a positive control with IC50 value of 9.30 µM. In kinetic evaluation against tyrosinase, 4m depicted a mixed inhibition pattern. Additionally, antioxidant evaluations exhibited moderate to weak potency in 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The detailed interactions and binding mode toward tyrosinase of the most potent derivative were explicated by molecular docking study. Moreover, the computer-aided drug-likeness and pharmacokinetic studies were also carried out. © 2021
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