In the current study, an efficient synthesis of new triazole-linked chalcone 3a-g scaffold was performed by multistep reaction sequence and was screened for their antibacterial activity against Pseudomonas aeruginosa, Escherchia coli, Staphylococcus aureus and Bacillus subtilis. The preliminary result revealed that 3f exhibited a promising antibacterial activity. Furthermore, 3f was modified at alpha, beta- unsaturated carbonyl segment to isoxazoline 4a, pyrimidines 5a, 6a-b, pyrazoles 7a-c and cyanopyridine 8a. Within the modified compounds 7b (4-nitro-substituted pyrazole) turn to be more potent against all bacterial strains. In addition compounds, 5a and 8a showed promising free radical scavenging activity.