Next Article in Journal
Serine Proteases-Like Genes in the Asian Rice Gall Midge Show Differential Expression in Compatible and Incompatible Interactions with Rice
Next Article in Special Issue
Chemometric Analysis of the Amino Acid Requirements of Antioxidant Food Protein Hydrolysates
Previous Article in Journal
Membrane-Based Inverse Transition Cycling: An Improved Means for Purifying Plant-Derived Recombinant Protein-Elastin-Like Polypeptide Fusions
Previous Article in Special Issue
3D-QSAR and Molecular Docking Studies on Derivatives of MK-0457, GSK1070916 and SNS-314 as Inhibitors against Aurora B Kinase
Article Menu

Export Article

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

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

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 / 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)
View Full-Text   |   Download PDF [745 KB, 19 June 2014; original version 19 June 2014]   |  

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 (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top