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

被引：80

作者：

Mladenovic, Milan ^{[1
]}

Mihailovic, Mirjana ^{[2
]}

Bogojevic, Desanka ^{[2
]}

Matic, Sanja ^{[3
]}

Niciforovic, Neda ^{[1
]}

Mihailovic, Vladimir ^{[1
]}

Vukovic, Nenad ^{[1
]}

Sukdolak, Slobodan ^{[1
]}

Solujic, Slavica ^{[1
]}

机构：

[1] Univ Kragujevac, Fac Sci, Dept Chem, Kragujevac 34000, Serbia

[2] Univ Belgrade, Inst Biol Res, Dept Mol Biol, Belgrade 11000, Serbia

[3] Univ Kragujevac, Fac Sci, Dept Biol End Ecol, Kragujevac 34000, Serbia

来源：

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES | 2011年 / 12卷 / 05期

关键词：

4-hydroxycoumarins; antioxidant activity in vitro; DFT; BDEs; QSAR; design; CORTEX;

D O I：

10.3390/ijms12052822

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

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.

引用

页码：2822 / 2841

页数：20

共 36 条

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