Interactions of (2E)-1-(4-chlorophenyl)-3-(3,4 dimethoxyphenyl)prop-2-en-1-one with various substituted thioureas such as thiourea, N-phenylthiourea, 2-chlorophenylthiourea, 3-chlorophenylthiourea and 4-chlorophenylthiourea in presence of isopropanol as a medium. The products isolated in these reactions were characterized on the basis of conventional elemental analysis, chemical characteristics and spectral data. All the synthesized compounds screened against various microorganisms such as gram positive Staphylococcus aureus, gram-negative Escherichia coli. Ciprofloxacin was used as a standard drug for the antimicrobial screening.