Bioorganic & Medicinal Chemistry 2012-01-15

Antioxidant properties of 4-quinolones and structurally related flavones.

Jane Greeff, Jacques Joubert, Sarel F Malan, Sandra van Dyk

Index: Bioorg. Med. Chem. 20 , 809-18, (2012)

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Abstract

Neurodegenerative disorders are frequently associated with increased oxidative damage to the brain as a result of free radicals produced by cellular respiration. The onset and progression of neurodegeneration may therefore be curbed by exogenous hydrogen-donating antioxidant moieties such as the naturally occurring flavonoids. A series of 2-phenylquinolin-4(1H)-ones was synthesised and displayed moderate to high antioxidant activity when compared to structurally related flavones and quinolines. Activity of the hydroxy-2-phenylquinolin-4(1H)-ones (8-10) was established in reducing ferrous ions and diminishing hydrogen peroxide and hydroxyl radical production, in the FRAP (1.41-97.71% Trolox equivalents), ORAC (9.18-15.27 μM Trolox equivalents at 0.00 1mM) and TBARS (0.05-0.72 nmol MDA/mg tissue) assays, respectively. The results indicated that the additional hydrogen donating groups on the synthesised 2-phenylquinolin-4(1H)-one series increased antioxidant activity.Copyright © 2011 Elsevier Ltd. All rights reserved.