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

Milan Mladenović 1,* email, Mirjana Mihailović 2 email, Desanka Bogojević 2 email, Sanja Matić 3 email, Neda Nićiforović 1 email, Vladimir Mihailović 1 email, Nenad Vuković 1 email, Slobodan Sukdolak 1 email and Slavica Solujić 1 email
1 Department of Chemistry, Faculty of Science, P.O. Box 60, University of Kragujevac, Radoja Domanovića 12, 34000 Kragujevac, Serbia 2 Department of Molecular Biology, Institute for Biological Research, University of Belgrade, Bulevar Despota Stefana 142, 11000 Beograd, Serbia 3 Department of Biology end Ecology, Faculty of Science, P.O. Box 60, University of Kragujevac, Radoja Domanovića 12, 34000 Kragujevac, Serbia
* Author to whom correspondence should be addressed.
Received: 3 February 2011; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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. International Journal of Molecular Sciences. 2011; 12(5):2822-2841.

Chicago/Turabian Style

Mladenović, Milan; Mihailović, Mirjana; Bogojević, Desanka; Matić, Sanja; Nićiforović, Neda; Mihailović, Vladimir; Vuković, Nenad; Sukdolak, Slobodan; Solujić, Slavica. 2011. "In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies." Int. J. Mol. Sci. 12, no. 5: 2822-2841.

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