Synthesis, Biological Properties, and Molecular Docking Study of Novel 1,2,3-Triazole-8-quinolinol Hybrids

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dc.authoridWarad, Ismail/0000-0001-8853-8961
dc.authoridTUZUN, BURAK/0000-0002-0420-2043
dc.contributor.authorEl Faydy, Mohamed
dc.contributor.authorLakhrissi, Loubna
dc.contributor.authorDahaieh, Naoufel
dc.contributor.authorOunine, Khadija
dc.contributor.authorTuzun, Burak
dc.contributor.authorChahboun, Nabila
dc.contributor.authorBoshaala, Ahmed
dc.date.accessioned2024-10-26T18:11:25Z
dc.date.available2024-10-26T18:11:25Z
dc.date.issued2024
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractA new series of 1,2,3-triazole-8-quinolinol hybrids were synthesized in good yields using monosubstituted acetonitriles and 5-azidomethyl-8-quinolinol as the starting reagents via a one-step protocol. The structures of 1,2,3-triazole-8-quinolinol hybrids were characterized by nuclear magnetic resonance (H-1 and C-13 NMR) spectroscopy and elemental analysis. Antibacterial activity in vitro of all the synthesized hybrids was investigated against Escherichia coli (E. coli), Xanthomonas fragariae (X. fragariae), Staphylococcus aureus (S. aureus), and Bacillus subtilis (B. subtilis) applying the methods of disk diffusion and minimal inhibition concentration (MIC). Hybrid 7 exhibited excellent antibacterial capacity, with an MIC value of 10 mu g/mL against S. aureus and 20 mu g/mL against B. subtilis, E. coli, and X. fragariae, which were comparable to those that of the standard antibiotic nitroxoline. A structure-activity relationship (SAR) study of 1,2,3-triazole-8-quinolinol hybrids showed that introducing electron-donating substituents in the 1,2,3-triazole ring at the 4-position is important for activity. Quantum chemical calculations have been undertaken to employ the Gaussian software in the B3LYP, HF, and M062X basis sets using 3-21g, 6-31g, and SDD levels to further explain linkages within the antibacterial findings. Furthermore, molecular docking investigations were also conducted to investigate the binding affinities as well as the interactions of some hybrids with the target proteins. An absorption, distribution, metabolism, excretion, and toxicity (ADME/T) investigation was carried out to scrutinize the viability of employing the 1,2,3-triazole-8-quinolinol hybrids as medicines.
dc.description.sponsorshipKing Saud University [RSP2024R381]; King Saud University, Riyadh, Saudi Arabia; National Centre for Scientific and Technical Research (CNRST) of Morocco; UATRS Division
dc.description.sponsorshipThe authors extend their appreciation to the Researchers Supporting Project number (RSP2024R381), King Saud University, Riyadh, Saudi Arabia. The authors would like to thank the National Centre for Scientific and Technical Research (CNRST) of Morocco for putting at their disposal the technical facilities of the UATRS Division
dc.identifier.doi10.1021/acsomega.4c03906
dc.identifier.endpage25409
dc.identifier.issn2470-1343
dc.identifier.issue23
dc.identifier.pmid38882066
dc.identifier.scopus2-s2.0-85195032252
dc.identifier.scopusqualityQ1
dc.identifier.startpage25395
dc.identifier.urihttps://doi.org/10.1021/acsomega.4c03906
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30665
dc.identifier.volume9
dc.identifier.wosWOS:001237227700001
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofAcs Omega
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.titleSynthesis, Biological Properties, and Molecular Docking Study of Novel 1,2,3-Triazole-8-quinolinol Hybrids
dc.typeArticle

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