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, 1H NMR, 13C 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.