Synthesis of N-substituted indole-2-carboxamides and investigation of their biochemical responses against free radicals.
The antioxidant role of novel N-substituted indole-2-carboxamides (I2CDs) was investigated for their inhibitory effects on superoxide anion (O2-) and lipid peroxidation (LP). Among the synthesized I2CDs, 3, 4, 6, 8 and 9 significantly inhibited O2*- with an inhibition range at 70-98%. Examination of substituent effects on activity showed that both the ortho- and para- positions of the benzamide residue needs to be dichlorinated in order to get a maximum inhibitory effect on superoxide anion. In general, halogenated derivatives were found more active then the non-halogenated ones. However, none of the I2CDs had a significant inhibitory effects on the level of lipid peroxidation; only compounds 7 and 10 moderately decreased LP levels by over 50% at 10(-3) M concentrations.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ankara, Tandogan, Ankara, Turkey.
Pinar
P
Bozkaya
Sureyya
S
Olgen
Tulay
T
Coban
Dogu
D
Nebioglu
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D066298:In Vitro Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015227:Lipid Peroxidation / Q000187:drug effects; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000378:metabolism
D000975:Antioxidants; D016166:Free Radical Scavengers; D007211:Indoles; D013481:Superoxides