Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents.
In the present work, new indole-based chalcone derivatives were obtained via the reaction of 5-substituted-1H-indole-3-carboxaldehydes/1-methylindole-3-carboxaldehyde with appropriate acetophenones. The synthesized compounds were investigated for their in vitro COX-1 and COX-2 inhibitory activity. The most effective COX inhibitors were also evaluated for their in vivo antiinflammatory and antioxidant activities in LPS induced sepsis model. Furthermore, the CCK-8 assay was carried out to determine cytotoxic effects of all compounds against NIH/3T3 mouse embryonic fibroblast cells. 3-(5-Bromo-1H-indol-3-yl)-1-(4-cyanophenyl)prop-2-en-1-one (6) can be considered as a non-selective COX inhibitor (COX-1 IC50 = 8.1 ± 0.2 μg/mL, COX-2 IC50 = 9.5 ± 0.8 μg/mL), whereas 3-(5-methoxy-1H-indol-3-yl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one (1) inhibited only COX-1 (IC50 = 8.6 ± 0.1 μg/mL). According to in vivo studies, these compounds also displayed antiinflammatory and antioxidant activities.
['Özdemir|Ahmet|A|', 'Altintop|Mehlika Dilek|MD|', 'Turan-Zitouni|Gülhan|G|', 'Çiftçi|Gülşen Akalın|GA|', 'Ertorun|İpek|İ|', 'Alataş|Özkan|Ö|', 'Kaplancikli|Zafer Asim|ZA|']
D000818:Animals D002470:Cell Survival D047188:Chalcones D051545:Cyclooxygenase 1 D051546:Cyclooxygenase 2 D016861:Cyclooxygenase Inhibitors D004195:Disease Models, Animal D015195:Drug Design D004353:Drug Evaluation, Preclinical D007211:Indoles D015227:Lipid Peroxidation D008111:Liver Function Tests D008565:Membrane Proteins D051379:Mice D015394:Molecular Structure D041681:NIH 3T3 Cells D018384:Oxidative Stress D018805:Sepsis
Chalcone Cyclooxygenase Indole