Design and synthesis of novel quinolinone-3-aminoamides and their alpha-lipoic acid adducts as antioxidant and anti-inflammatory agents.
A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the alpha-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.
Detsi
Anastasia
A
Laboratory of Organic Chemistry, School of Chemical Engineering, National Technical University of Athens, Zorgafou Campus, GR 157 73, Athens, Greece. adetsi@chemeng.ntua.gr
Bouloumbasi
Dionysia
D
Prousis
Kyriakos C
KC
Koufaki
Maria
M
Athanasellis
Giorgos
G
Melagraki
Georgia
G
Afantitis
Antreas
A
Igglessi-Markopoulou
Olga
O
Kontogiorgis
Christos
C
Hadjipavlou-Litina
Dimitra J
DJ
D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry; D002351:Carrageenan; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005260:Female; D006834:Hydrazines / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D010084:Oxidation-Reduction; D010851:Picrates; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011916:Rats, Inbred F344; D013329:Structure-Activity Relationship; D008063:Thioctic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology
D000577:Amides; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D001713:Biphenyl Compounds; D006834:Hydrazines; D016859:Lipoxygenase Inhibitors; D010851:Picrates; D015363:Quinolones; D017665:Hydroxyl Radical; D008063:Thioctic Acid; D002351:Carrageenan; C004931:1,1-diphenyl-2-picrylhydrazyl; D004121:Dimethyl Sulfoxide