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Int. J. Mol. Sci. 2011, 12(5), 2822-2841; doi:10.3390/ijms12052822
Article

In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies

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Received: 3 February 2011 / Revised: 15 March 2011 / Accepted: 13 April 2011 / Published: 29 April 2011
(This article belongs to the Special Issue Recent Advances in QSAR/QSPR Theory)
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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.
Keywords: 4-hydroxycoumarins; antioxidant activity in vitro; DFT; BDEs; QSAR; design 4-hydroxycoumarins; antioxidant activity in vitro; DFT; BDEs; QSAR; design
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Mladenović, M.; Mihailović, M.; Bogojević, D.; Matić, S.; Nićiforović, N.; Mihailović, V.; Vuković, N.; Sukdolak, S.; Solujić, S. In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies. Int. J. Mol. Sci. 2011, 12, 2822-2841.

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