Abstract
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
Medicinal Chemistry
Title:Antioxidant Activity of New Benzo[de]quinolines and Lactams: 2DQuantitative Structure-Activity Relationships
Volume: 8 Issue: 5
Author(s): Alina Ghinet, Amaury Farce, Souhila Oudir, Jean Pommery, Joseph Vamecq, Jean-Pierre Henichart, Benoit Rigo and Philippe Gautret
Affiliation:
Keywords: Lactam, hydroxyketolactam, benzo[de]quinoline, antioxidant agent, 2D-QSAR, melatonin, methanol, chromatography, silica gel, NaHCO3
Abstract: 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.
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Cite this article as:
Ghinet Alina, Farce Amaury, Oudir Souhila, Pommery Jean, Vamecq Joseph, Henichart Jean-Pierre, Rigo Benoit and Gautret Philippe, Antioxidant Activity of New Benzo[de]quinolines and Lactams: 2DQuantitative Structure-Activity Relationships, Medicinal Chemistry 2012; 8 (5) . https://dx.doi.org/10.2174/157340612802084216
DOI https://dx.doi.org/10.2174/157340612802084216 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |
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