Study of two combined series of triketones with HPPD inhibitory activity by molecular modelling

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorCapucho, L. R.-
Autor(es): dc.creatorCunha, E. F. F. da-
Autor(es): dc.creatorFreitas, M. P.-
Data de aceite: dc.date.accessioned2026-02-09T11:36:17Z-
Data de disponibilização: dc.date.available2026-02-09T11:36:17Z-
Data de envio: dc.date.issued2023-10-18-
Data de envio: dc.date.issued2023-10-18-
Data de envio: dc.date.issued2022-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/58434-
Fonte completa do material: dc.identifierhttps://www.tandfonline.com/doi/full/10.1080/1062936X.2023.2192521-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1143343-
Descrição: dc.descriptionTriketones are suitable compounds for 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibition and are important compounds for eliminating agricultural weeds. We report herein quantitative structure-activity relationship (QSAR) modelling and docking studies for a series of triketone-quinoline hybrids and 2-(aryloxyacetyl)cyclohexane-1,3-diones with the aim of proposing new chemical candidates that exhibit improved performance as herbicides. The QSAR models obtained were reliable and predictive (average r2, q2, and r2pred of 0.72, 0.51, and 0.71, respectively). Guided by multivariate image analysis of the PLS regression coefficients and variable importance in projection scores, the substituent effects could be analysed, and a promising derivative with R1 = H, R2 = CN, and R3 = 5,7,8-triCl at the triketone-quinoline scaffold (P18) was proposed. Docking studies demonstrated that π–π stacking interactions and specific interactions between the substituents and amino acid residues in the binding site of the Arabidopsis thaliana HPPD (AtHPPD) enzyme support the desired bioactivity. In addition, compared to a benchmark commercial triketone (mesotrione), the proposed compounds are more lipophilic and less mobile in soil rich in organic matter and are less prone to contaminate groundwater.-
Idioma: dc.languageen-
Publicador: dc.publisherTaylor and Francis Online-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceSAR and QSAR in Environmental Research-
Palavras-chave: dc.subjectTriketones-
Palavras-chave: dc.subjectHPPD enzyme-
Palavras-chave: dc.subjectQuantitative structure-activity relationship (QSAR)-
Palavras-chave: dc.subjectDocking-
Palavras-chave: dc.subjectHerbicide-
Título: dc.titleStudy of two combined series of triketones with HPPD inhibitory activity by molecular modelling-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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