Antioxidant properties of 4-quinolones and structurally related flavones

作者:Greeff Jane; Joubert Jacques; Malan Sarel F; van Dyk Sandra*
来源:Bioorganic & Medicinal Chemistry, 2012, 20(2): 809-818.
DOI:10.1016/j.bmc.2011.11.068

摘要

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 (R) equivalents), ORAC (9.18-15.27 mu M Trolox (R) equivalents at 0.001 mM) 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.