2,3-Dichloronaphthoquinone derivatives: Synthesis, antimicrobial activity, molecular modelling and ADMET studies

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dc.authoridOzcan, hafize/0000-0002-8031-6755
dc.authoridEce, Abdulilah/0000-0002-3087-5145
dc.authorwosidOzcan, hafize/KJM-5364-2024
dc.authorwosidEce, Abdulilah/W-4165-2017
dc.contributor.authorKolancilar, Hakan
dc.contributor.authorOzcan, Hafize
dc.contributor.authorYilmaz, Ays en uekinci
dc.contributor.authorSalan, Alparslan Semih
dc.contributor.authorEce, Abdulilah
dc.date.accessioned2024-06-12T11:12:25Z
dc.date.available2024-06-12T11:12:25Z
dc.date.issued2024
dc.departmentTrakya Üniversitesien_US
dc.description.abstractIn the present study, an intermediate namely 2-(3-bromopropylamino)-3-chloronaphthalene-1,4-dione was initially synthesized via the nucleophilic addition-elimination reaction between 2,3-dichloro-1,4-naphthoquinone and 3-bromo-1-aminopropane. Then a coupling reaction between the intermediate and piperazine derivatives yielded a number of 1,4-naphthoquinone derivatives. Spectroscopic analysis successfully characterized the products that were obtained in good yields. In vitro antibacterial properties of the compounds were examined against different bacterial strains. In vitro antibacterial properties of the compounds were examined against the bacterial strains S. Aureus, E. Faecalis, E. Coli and P. Aeruginosa. While compound 9 was found to be effective against all bacterial strains used, compound 12 was active against three strains and compounds 10 and 11 were effective against the two. None of the compounds are effective against C. albicans strain. In silico molecular docking studies revealed that all compounds had docking scores comparable to the antibacterial drugs ciprofloxacin and gentamicin and might be considered as DNA gyrase B inhibitors. Molecular dynamics simulations were also conducted for a better understanding of the stability and the selected docked complexes. Additionally, the drug similarity of the synthesized compounds and ADMET characteristics were examined in conjunction with the antibiotic ciprofloxacin, and drug potentials were then evaluated. Compatible predictions were found with the drug similarity and ADMET parameters.en_US
dc.identifier.doi10.1016/j.bioorg.2024.107300
dc.identifier.issn0045-2068
dc.identifier.issn1090-2120
dc.identifier.pmid38522391en_US
dc.identifier.scopus2-s2.0-85188696075en_US
dc.identifier.scopusqualityQ1en_US
dc.identifier.urihttps://doi.org/10.1016/j.bioorg.2024.107300
dc.identifier.urihttps://hdl.handle.net/20.500.14551/23167
dc.identifier.volume146en_US
dc.identifier.wosWOS:001214629100001en_US
dc.identifier.wosqualityN/Aen_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherAcademic Press Inc Elsevier Scienceen_US
dc.relation.ispartofBioorganic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectPiperazineen_US
dc.subject4-Naphthoquinoneen_US
dc.subjectDNA Gyraseen_US
dc.subjectMicrodilution Methoden_US
dc.subjectMolecular Dynamicsen_US
dc.subjectDrug -Likenessen_US
dc.subject1,4-Naphthoquinone Derivativesen_US
dc.subjectDna Gyraseen_US
dc.subjectAntifungalen_US
dc.subjectAnticanceren_US
dc.subjectDockingen_US
dc.subjectDesignen_US
dc.title2,3-Dichloronaphthoquinone derivatives: Synthesis, antimicrobial activity, molecular modelling and ADMET studiesen_US
dc.typeArticleen_US

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