A new series of cinnamic acid amide and cinnamaldehyde Schiff base were synthesized by coupling cinnamic acid to different amino acids. The synthesized compounds were characterized and compared by reported NMR spectroscopy and analytical data. All the synthesized compounds were evaluated for in vitro antimicrobial activities. Among the tested compounds 6c and 6e showed potential antimicrobial activities. Further antimicrobial results were supported by in silico molecular docking study. Compounds 6c and 6e were found to be more selective toward HpPDF(PDB ID: 4E9A). Among all these synthesized compounds, 2-(cinnamamido)-3-(1H-imidazol-4-yl)propanoic acid (6e) emerged as most potent active molecule with antimicrobial activity for Klebbsiella pneumoniae.