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Title: In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies
Authors: Mladenović M.
Mihailovic, Mirjana
Bogojević, Desanka
Matić, Sanja
Martinović, Neda
Mihailovic, Vladimir
Vukovic, Nenad
Sukdolak S.
Solujic A.
Journal: International Journal of Molecular Sciences
Issue Date: 1-May-2011
Abstract: The series of fifteen synthesized 4-hydroxycoumarin derivatives was subjected to antioxidant activity evaluation in vitro, through total antioxidant capacity, 1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydroxyl radical, lipid peroxide scavenging and chelating activity. The highest activity was detected during the radicals scavenging, with 2b, 6b, 2c, and 4c noticed as the most active. The antioxidant activity was further quantified by the quantitative structure-activity relationships (QSAR) studies. For this purpose, the structures were optimized using Paramethric Method 6 (PM6) semi-empirical and Density Functional Theory (DFT) B3LYP methods. Bond dissociation enthalpies of coumarin 4-OH, Natural Bond Orbital (NBO) gained hybridization of the oxygen, acidity of the hydrogen atom and various molecular descriptors obtained, were correlated with biological activity, after which we designed 20 new antioxidant structures, using the most favorable structural motifs, with much improved predicted activity in vitro. © 2011 by the authors.
Type: Article
DOI: 10.3390/ijms12052822
SCOPUS: 79957795403
Appears in Collections:Faculty of Science, Kragujevac
Institute for Information Technologies, Kragujevac
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