Antioxidant Activity of New Benzo[de]quinolines and Lactams: 2DQuantitative Structure-Activity Relationships

Author(s): Alina Ghinet, Amaury Farce, Souhila Oudir, Jean Pommery, Joseph Vamecq, Jean-Pierre Henichart, Benoit Rigo, Philippe Gautret.

Journal Name: Medicinal Chemistry

Volume 8 , Issue 5 , 2012

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In order to predict the antioxidant activity of 7 polycyclic lactams, a two dimensional quantitative-structure activity relationships (2D-QSAR) study based on a 5-descriptor model was performed. The synthetic compounds built from a condensed lactam scaffold were screened for their abilities to inhibit the autoxidation of pyrogallol, a superoxide anion radical-dependent process. The ketone 2 (8,9-dihydro-7H-benzo[de]pyrrolo[1,2-a]quinoline-7,10(7aH)-dione) exhibited the most potent antioxidant activity in vitro. The oxidation mechanism was proved by the isolation and characterization of alcohol 5 formed in the reaction of ketone 2 with dissolved oxygen in methanol.

Keywords: Lactam, hydroxyketolactam, benzo[de]quinoline, antioxidant agent, 2D-QSAR, melatonin, methanol, chromatography, silica gel, NaHCO3

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Article Details

Year: 2012
Page: [942 - 946]
Pages: 5
DOI: 10.2174/157340612802084216
Price: $58

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