A new quinolinone-chalcone hybrid with potential antibacterial and herbicidal properties using in silico approaches

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dc.creatorDuarte, Vitor Santos
dc.creatorPaula, Renata Layse Gonçalves de
dc.creatorCustodio, Jean Marcos Ferreira
dc.creatorD´Oliveira, Giulio Demetrius Creazzo
dc.creatorBorges, Leonardo Luiz
dc.creatorNoda Pérez, Caridad
dc.creatorPerjesi, Pal
dc.creatorOliver, Allen G.
dc.creatorNapolitano, Hamilton Barbosa
dc.date.accessioned2023-08-21T13:05:17Z
dc.date.available2023-08-21T13:05:17Z
dc.date.issued2022
dc.description.abstractQuinolinone-chalcones are hybrid compounds consisting of chalcone and quinolone moieties with biological activity related to their hybrid structure. This work seeks to describe the structural and theoretical parameters related to the physicochemical properties and biological activity of a new quinolinone-chalcone. The synthesis, structural characterization by X-ray diffraction, molecular topology by Hirshfeld surfaces and QTAIM, molecular electronic calculations, and pharmacophore analysis were described. The weak interactions C–H…O, C–H…π, and C–H…Br were responsible for crystal growth and stabilized the crystalline state. The DFT analysis shows that the sulfonamide group region is susceptible to observed interactions, and the frontier molecular orbitals indicate high kinetic stability. Also, pharmacophore analysis revealed potential antibacterial and herbicidal activity; by docking within the active site of TtgR, a transcription regulator for the efflux pump TtgABC from the highly resistant Pseudomonas putida (P. putida) strain DOT-TIE, we showed that the activation of TtgR relies upon the binding of aromatic-harboring compounds, which plays a crucial role in bacterial evasion. In this context, a new quinolinone-chalcone has a higher binding affinity than tetracycline, which suggests it might be a better effector for TtgR.pt_BR
dc.identifier.citationDUARTE, Vitor S. et al. A new quinolinone-chalcone hybrid with potential antibacterial and herbicidal properties using in silico approaches. Journal of Molecular Modeling, London, v. 28, e176, 2022. DOI: 10.1007/s00894-022-05140-9. Disponível em: https://link.springer.com/article/10.1007/s00894-022-05140-9. Acesso em: 17 ago. 2023.pt_BR
dc.identifier.doi10.1007/s00894-022-05140-9
dc.identifier.issne- 0948-5023
dc.identifier.issn1610-2940
dc.identifier.urihttps://link.springer.com/article/10.1007/s00894-022-05140-9
dc.language.isoengpt_BR
dc.publisher.countryGra-bretanhapt_BR
dc.publisher.departmentInstituto de Química - IQ (RMG)pt_BR
dc.rightsAcesso Restritopt_BR
dc.subjectQuinolinone-chalconept_BR
dc.subjectQTAIM analysispt_BR
dc.subjectMolecular modelingpt_BR
dc.subjectPotential herbicide activitypt_BR
dc.titleA new quinolinone-chalcone hybrid with potential antibacterial and herbicidal properties using in silico approachespt_BR
dc.typeArtigopt_BR

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