title: In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies.
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.
authors.affiliation: Department of Chemistry, Faculty of Science, P.O. Box 60, University of Kragujevac, Radoja Domanovića 12, 34000 Kragujevac, Serbia; E-Mails: nneda@kg.ac.rs (N.N.); vladam@kg.ac.rs (V.M.); nvukovic@kg.ac.rs (N.V.); duda@kg.ac.rs (S.S.); ssolujic@kg.ac.rs (S.S.).
authors.forename: Milan
authors.initials: M
authors.lastname: Mladenović
authors.forename: Mirjana
authors.initials: M
authors.lastname: Mihailović
authors.forename: Desanka
authors.initials: D
authors.lastname: Bogojević
authors.forename: Sanja
authors.initials: S
authors.lastname: Matić
authors.forename: Neda
authors.initials: N
authors.lastname: Nićiforović
authors.forename: Vladimir
authors.initials: V
authors.lastname: Mihailović
authors.forename: Nenad
authors.initials: N
authors.lastname: Vuković
authors.forename: Slobodan
authors.initials: S
authors.lastname: Sukdolak
authors.forename: Slavica
authors.initials: S
authors.lastname: Solujić
mesh_terms: D015110:4-Hydroxycoumarins / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D008054:Lipid Peroxides / Q000737:chemistry; D008958:Models, Molecular; D010851:Picrates / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship; D013329:Structure-Activity Relationship
chemical_list: D015110:4-Hydroxycoumarins; D000975:Antioxidants; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D005609:Free Radicals; D008054:Lipid Peroxides; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl