MICROWAVE ASSISTED SYNTHESIS AND BIOLOGICAL EVALUATION OF POTENTIAL QUINOLINE-2-CARBOXYLATES OF AROMATIC COMPOUNDS
Edakot Fazal1,Pushpa S Murthy2,Kamatham A Naidu3,Ankisetty Maheshwaraiah3, Subban Nagarajan2, Belgur S Sudha1
1Department of Chemistry, Yuvaraja's College, University of Mysore, Mysore-570 005, India;
2 Department of Spice and Flavor Science, CSIR-Central Food Technological Research institute, Mysore-570005,
3Department of Biochemistry & Nutrition, CSIR-Central Food Technological Research institute, Mysore-570005.
Abstract
Quinoline, a heterocyclic scaffold which is well known for wide spectrum of biological activities.Quinoline-2-carboxylates with aromatic compounds and a terpene is synthesized under microwave which increased the yield and shortens the reaction time comparing to conventional method reported by us. The synthesized compounds are characterized by UV-vis, IR, NMR and mass spectra and other physico-chemical methods.The compounds were evaluated for their in-vitro antioxidant, antimicrobial and antiplatelet activities. The compound 3k(2-methoxyphenyl quinoline-2-carboxylate)and 3c (p-tolyl quinoline-2-carboxylate showed potential antioxidant activity evaluated by DDPH radical scavenging activity. Anti-oxidant activity of 3k is confirmed by liver microsomal lipid peroxidation inhibition.3a(2-isopropyl-4-methylcyclohexyl quinoline-2-carboxylate), 3f (4-chlorophenyl quinoline-2-carboxylate) and 3g (4-chloro-3-methylphenyl quinoline-2-carboxylate) showed significant anti-inflammatory activity. In anti-microbial studies the compounds 3i (3,4-dimethylphenyl quinoline-2-carboxylate) and 3j (3,5-dimethylphenyl quinoline-2-carboxylate) inhibited antimicrobial growth significantly where as3a and 3h(2,5-dimethylphenyl quinoline-2-carboxylate) inhibited moderately. Inhibition of fungal growth was effective by3c, 3a(phenyl quinoline-2-carboxylate), 3c, 3d (o-tolyl quinoline-2-carboxylate), 3e(m-tolyl quinoline-2-carboxylate) and 3f.3k is a potential anti-platelet agent where as 3c is a moderate one.