MW Assisted Synthesis of New 4,6-diaryl-3,4-Didhydropyrimidines-2(1H)-thione Derivatives: Tyrosinase Inhibition, Antioxidant, and Molecular Docking Studies

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dc.contributor.authorFandaklı, Seda
dc.contributor.authorYücel, Tayyibe Beyza
dc.contributor.authorÖztürk, Elif
dc.contributor.authorUzuner, Uğur
dc.contributor.authorBarut, Burak
dc.contributor.authorAteş, Fatih Mehmet
dc.contributor.authorYaylı, Nurettin
dc.date.accessioned2024-10-04T19:06:31Z
dc.date.available2024-10-04T19:06:31Z
dc.date.issued2023
dc.departmentBayburt Üniversitesien_US
dc.description.abstractA number of new methoxy-substituted 4,6-diaryl-3,4-dihydropyrimidine-2(1H)-thiones (DH-Pyr-S, 17-28) were designed and synthesized by the reaction of methoxy-substituted chalcones (1–14) with thiourea using solid-phase microwave method (MW) in view of the structural requirements as suggested in the pharmacophore model for tyrosinase inhibition (TI). Synthesized compounds were assessed for their in vitro TI potential and compounds 16, 17, and 21 exhibited notable tyrosinase inhibitory properties at the concentrations of 31.86 ± 2.45 µM, 44.58 ± 0.46 µM, and 48.47 ± 0.66 µM, respectively. Compounds (16, 17, and 21) were exhibited experimentally more potent TI than the standard used in terms of the IC50 value (Kojic acid, 55.38 ± 2.30 µM; p<0.0001). Additionally, DPPH activity of 15-28 were evaluated and compound 17 showed the moderate DPPH activity (45.64 ± 0.34%). Binding affinities of synthesized molecules to the tyrosinase catalytic core were further investigated through in silico molecular docking studies using AutoDock Vina (version 1.2.5), discovery studio accelyrs (BIOVIA, Dassault Systèmes) and predicting small-molecule pharmacokinetic properties using graph-based signatures (pkCSM) programs were used for ADMET calculations. Among synthesized compounds 15, 21, and 24 revealed high binding affinity to tyrosinase active site with lowest binding free energy (?G) values of -7.9 kcal/mol, thereby outperformed kojic acid affinity. In conclusion most modeling results were in agreement with their experimental data, suggesting the TI potential of lead compounds.en_US
dc.identifier.doi10.17776/csj.1299843
dc.identifier.endpage696en_US
dc.identifier.issn2587-2680
dc.identifier.issn2587-246X
dc.identifier.issue4en_US
dc.identifier.startpage687en_US
dc.identifier.trdizinid1215652en_US
dc.identifier.urihttps://doi.org/10.17776/csj.1299843
dc.identifier.urihttps://search.trdizin.gov.tr/tr/yayin/detay/1215652
dc.identifier.urihttp://hdl.handle.net/20.500.12403/4559
dc.identifier.volume44en_US
dc.indekslendigikaynakTR-Dizinen_US
dc.language.isoenen_US
dc.relation.ispartofCumhuriyet Science Journalen_US
dc.relation.publicationcategoryMakale - Ulusal Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectDihydropyrimidine-2(1H)-thioneen_US
dc.subjectTyrosinase inhibitionen_US
dc.subjectDPPHen_US
dc.subjectADMETen_US
dc.subjectMolecular docking.en_US
dc.titleMW Assisted Synthesis of New 4,6-diaryl-3,4-Didhydropyrimidines-2(1H)-thione Derivatives: Tyrosinase Inhibition, Antioxidant, and Molecular Docking Studiesen_US
dc.typeArticleen_US

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