Synthesis, Characterization, Theoretical Analyses, and Investigation of Their Biological Activities of Acetovanillone-Derived Novel Benzyl Ethers

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dc.authoridTAHTACI, HAKAN/0000-0002-1557-6315
dc.contributor.authorCalkilic, Nazire Merve
dc.contributor.authorAlici, Hakan
dc.contributor.authorDirekel, Sahin
dc.contributor.authorTahtaci, Hakan
dc.date.accessioned2024-09-29T16:02:47Z
dc.date.available2024-09-29T16:02:47Z
dc.date.issued2022
dc.departmentKarabük Üniversitesien_US
dc.description.abstractIn this study, acetovanillone-derived novel benzyl ethers were synthesized as target compounds. For the synthesis of these target compounds, ketone derivatives (3a-b) were synthesized as the starting compounds. Compounds 4a-b, which are alcohol derivatives, were then synthesized from the reduction of these ketone derivatives. In the last stage of the synthesis study, benzyl ether derivatives (6a-h, 7a-h), the target compounds containing acetovanillone, were synthesized from the reaction of the alcohol derivatives (4a-b) with various benzyl halides (5a-h). The structures of the synthesized compounds were characterized by various spectroscopic methods (FT-IR, H-1 NMR, C-13 NMR, mass spectrometry, and elemental analysis). In vitro antileishmanial and antibacterial activity tests were then performed for all synthesized compounds. Biological activity tests showed that while only a few of the compounds had antileishmanial activity, most had antibacterial activity. In addition, the ADME parameters, pharmacokinetic properties, and drug-like nature of all compounds were theoretically investigated using the SwissADME webserver. Finally, molecular docking simulations were carried out to support in vitro investigations and evaluate the inhibition effect of the synthesized compounds on the 3IW2 (Mycobacterium tuberculosis (Mtb) Cyp125; Pdb ID: 3IW2) receptor structure. Also, possible binding sites of some compounds with high affinity to Mtb Cyp125 according to docking results were identified.en_US
dc.description.sponsorshipKarabuk University [FYL-2019-2064]en_US
dc.description.sponsorshipThe authors would like to thank the funding support from Karabuk University (FYL-2019-2064).en_US
dc.identifier.doi10.1080/10406638.2021.1950782
dc.identifier.endpage5695en_US
dc.identifier.issn1040-6638
dc.identifier.issn1563-5333
dc.identifier.issue8en_US
dc.identifier.scopus2-s2.0-85110923956en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage5671en_US
dc.identifier.urihttps://doi.org/10.1080/10406638.2021.1950782
dc.identifier.urihttps://hdl.handle.net/20.500.14619/5720
dc.identifier.volume42en_US
dc.identifier.wosWOS:000673828600001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherTaylor & Francis Ltden_US
dc.relation.ispartofPolycyclic Aromatic Compoundsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAcetovanilloneen_US
dc.subjectbenzyl ethersen_US
dc.subjectbiological activityen_US
dc.subjectADMEen_US
dc.subjectmolecular docking simulationen_US
dc.titleSynthesis, Characterization, Theoretical Analyses, and Investigation of Their Biological Activities of Acetovanillone-Derived Novel Benzyl Ethersen_US
dc.typeArticleen_US

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