Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents

A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the α-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and fo...

Full description

Saved in:
Bibliographic Details
Published in:Journal of medicinal chemistry 2007-05, Vol.50 (10), p.2450-2458
Main Authors: Detsi, Anastasia, Bouloumbasi, Dionysia, Prousis, Kyriakos C, Koufaki, Maria, Athanasellis, Giorgos, Melagraki, Georgia, Afantitis, Antreas, Igglessi-Markopoulou, Olga, Kontogiorgis, Christos, Hadjipavlou-Litina, Dimitra J
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Amides - pharmacology
Animals
Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Antioxidants - chemical synthesis
Antioxidants - pharmacology
Biological and medical sciences
Biphenyl Compounds - chemistry
Bones, joints and connective tissue. Antiinflammatory agents
Carrageenan
Dimethyl Sulfoxide - chemistry
Edema - chemically induced
Edema - drug therapy
Female
Hydrazines - chemistry
Hydroxyl Radical - chemistry
Lipoxygenase Inhibitors - chemical synthesis
Lipoxygenase Inhibitors - pharmacology
Male
Medical sciences
Oxidation-Reduction
Pharmacology. Drug treatments
Picrates
Quinolones - chemical synthesis
Quinolones - pharmacology
Rats
Rats, Inbred F344
Structure-Activity Relationship
Thioctic Acid - analogs & derivatives
Thioctic Acid - chemical synthesis
Thioctic Acid - pharmacology
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the α-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure−activity relationships and an attempt is made to define the structural features required for activity.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm061173n