Linking quinoline ring to 5-nitrofuran moiety via sulfonyl hydrazone bridge: Synthesis, structural characterization, DFT studies, and evaluation of antibacterial and antifungal activity

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dc.authoridGunduz, Miyase Gozde/0000-0002-2287-9509
dc.authoridHan, Muhammed Ihsan/0000-0001-5610-0869
dc.authoridSkaro Bogojevic, Sanja/0000-0001-5159-9461
dc.authoridCetinkaya, Yasin/0000-0001-6617-5055
dc.authoridNikodinovic-Runic, Jasmina/0000-0002-2553-977X
dc.contributor.authorDogan, Sengul Dilem
dc.contributor.authorOzcan, Esma
dc.contributor.authorCetinkaya, Yasin
dc.contributor.authorHan, Muhammed Ihsan
dc.contributor.authorSahin, Onur
dc.contributor.authorBogojevic, Sanja Skaro
dc.contributor.authorNikodinovic-Runic, Jasmina
dc.date.accessioned2025-03-23T19:39:20Z
dc.date.available2025-03-23T19:39:20Z
dc.date.issued2023
dc.departmentSinop Üniversitesi
dc.description.abstractIn the present work, we report the synthesis, structural characterization, and computational studies of (E)-N'-((5nitrofuran-2-yl)methylene)quinoline-8-sulfonohydrazide (QNF) as a potential antimicrobial drug candidate. To design the target molecule, we utilized a molecular hybridization technique that connects two antimicrobial pharmacophores (quinoline and 5-nitrofuran rings) with a sulfonyl hydrazone moiety. QNF was synthesized by the condensation of quinoline-8-sulfonohydrazide with 5-nitrofuran-2-carbaldehyde, and characterized by various spectral techniques including single-crystal X-ray crystallography. QNF was extensively evaluated for its antibacterial and antifungal activity. The inhibition capacity of QNF on Candida albicans filamentation and biofilm formation was further investigated. Biofilm inhibition of QNF against C. albicans was supported by molecular docking studies in the binding site of agglutinin-like sequence 3 (Als3). Drug-like profile of QNF was confirmed by in silico calculation of its significant physicochemical properties. Additionally, the optimized geometrical structure, natural bond orbital calculations, frontier molecular orbital and molecular electrostatic potential analysis of QNF were carried out using the density functional theory method at the B3LYP with 6-31+G (d,p) basis set. The predictions of 1H and 13C NMR chemical shift values were performed using the gauge-independent atomic orbital method. Structural parameters and NMR values obtained experimentally were compared with the calculated values.
dc.description.sponsorshipAtatuerk University; Ministry of Education, Science and Technological Development of the Republic of Serbia [451-03-47/2023-01/200042]
dc.description.sponsorshipFinancial support from Atatuerk University is gratefully acknowledged. Authors also thank for the computer time provided by TUBITAK-ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). MGG would like to thank Prof. Dr. Gerhard Wolber, Freie Universitat Berlin, for providing the license for LigandScout 4.4. SSB and JNR were partially supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia, 451-03-47/2023-01/200042.
dc.identifier.doi10.1016/j.molstruc.2023.136155
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85165535055
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2023.136155
dc.identifier.urihttps://hdl.handle.net/11486/6322
dc.identifier.volume1292
dc.identifier.wosWOS:001049003500001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectAntimicrobial
dc.subjectHydrogen bond
dc.subjectIntramolecular interactions
dc.subjectDensity functional theory
dc.subjectX-ray diffraction
dc.subjectMolecular docking
dc.titleLinking quinoline ring to 5-nitrofuran moiety via sulfonyl hydrazone bridge: Synthesis, structural characterization, DFT studies, and evaluation of antibacterial and antifungal activity
dc.typeArticle

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