2013Arabian Journal of ChemistryOpen access

Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents

Rajappa S. Kenchappa, Yadav D. Bodke, A. Chandrashekar, Sandeep Telkar, K. S. Manjunatha, M. Aruna Sindhe

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Abstract

A convenient one-pot, three-component synthesis of 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives ( 3a–k ) by Chichibabin reaction has been reported. These compounds were synthesized by the reaction of 3-acetyl coumarin ( 1a ) or 5-bromo 3-acetyl coumarin ( 1b ) with substituted aromatic aldehydes ( 2a–k ) and ammonium acetate under acidic conditions and the structure was confirmed by FT-IR, 1 H NMR, 13 C NMR and Mass spectroscopic methods. The newly synthesized compounds ( 3a–k ) were evaluated for antimicrobial activity, DPPH free radical scavenging activity and ferrous ion-chelating ability. The mode of action of these active compounds was carried out by docking receptor GlcN6P synthase. Compounds 3a , 3b , 3c , and 3d have displayed potential antimicrobial activity and some of the compounds have shown promising antioxidant properties.

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A convenient one-pot, three-component synthesis of 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives ( 3a–k ) by Chichibabin reaction has been reported. These compounds were synthesized by the reaction of 3-acetyl coumarin ( 1a ) or 5-bromo 3-acetyl coumarin ( 1b ) with substituted aromatic aldehydes ( 2a–k ) and ammonium acetate under acidic conditions and the structure was confirmed by FT-IR, 1 H NMR, 13 C NMR and Mass spectroscopic methods. The newly synthesized compounds ( 3a–k ) were evaluated for antimicrobial activity, DPPH free radical scavenging activity and ferrous ion-chelating ability. The mode of action of these active compounds was carried out by docking receptor GlcN6P synthase. Compounds 3a , 3b , 3c , and 3d have displayed potential antimicrobial activity and some of the compounds have shown promising antioxidant properties.

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Available abstract

A convenient one-pot, three-component synthesis of 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives ( 3a–k ) by Chichibabin reaction has been reported. These compounds were synthesized by the reaction of 3-acetyl coumarin ( 1a ) or 5-bromo 3-acetyl coumarin ( 1b ) with substituted aromatic aldehydes ( 2a–k ) and ammonium acetate under acidic conditions and the structure was confirmed by FT-IR, 1 H NMR, 13 C NMR and Mass spectroscopic methods. The newly synthesized compounds ( 3a–k ) were evaluated for antimicrobial activity, DPPH free radical scavenging activity and ferrous ion-chelating ability. The mode of action of these active compounds was carried out by docking receptor GlcN6P synthase. Compounds 3a , 3b , 3c , and 3d have displayed potential antimicrobial activity and some of the compounds have shown promising antioxidant properties.

Key concepts: Chemistry, Coumarin, Antimicrobial, Pyridine, Ammonium acetate, Proton NMR, Chelation, DPPH

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