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In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies.

Mladenović M, Mihailović M, Bogojević D, Matić S, Nićiforović N, Mihailović V, Vuković N, Sukdolak S, Solujić S - Int J Mol Sci (2011)

Bottom Line: 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.

View Article: PubMed Central - PubMed

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.).

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.

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Designed 4-hydroxy-chromene-2H-one structures with predicted biological activity in vitro.
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f4-ijms-12-02822: Designed 4-hydroxy-chromene-2H-one structures with predicted biological activity in vitro.

Mentions: We have learned how carbonyl/carboxyl and substituted N-thiazole moieties contribute to our compounds antioxidant activity and, by the use of QSAR, we designed twenty new improved coumarin structures and calculated their values of potential scavenging and chelating activity (Figure 4).


In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies.

Mladenović M, Mihailović M, Bogojević D, Matić S, Nićiforović N, Mihailović V, Vuković N, Sukdolak S, Solujić S - Int J Mol Sci (2011)

Designed 4-hydroxy-chromene-2H-one structures with predicted biological activity in vitro.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3116159&req=5

f4-ijms-12-02822: Designed 4-hydroxy-chromene-2H-one structures with predicted biological activity in vitro.
Mentions: We have learned how carbonyl/carboxyl and substituted N-thiazole moieties contribute to our compounds antioxidant activity and, by the use of QSAR, we designed twenty new improved coumarin structures and calculated their values of potential scavenging and chelating activity (Figure 4).

Bottom Line: 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.

View Article: PubMed Central - PubMed

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.).

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.

Show MeSH
Related in: MedlinePlus