Abstract <p>This study involved synthesizing a new series of imides containing a 1,3,4-thiadiazole ring derived from ibuprofen via a ring-closure reaction. The first step in the synthetic route takes place with the cyclization of ibuprofen to form a thiadiazole intermediate, which was then reacted with benzoic acid via a coupling reaction. Then followed by esterification with methanol produced the methyl ester, which was converted into the benzohydrazide derivative. Finally, the imide derivatives are obtained by the fusion reaction of the acid hydrazide with suitable anhydrides. All synthesized compounds were identified using spectral methods (FT-IR, ¹H, ¹³C NMR). <i>In silico</i> molecular docking study was used to evaluate the interactions between the produced compounds and the COX-2 active site. The synthesized compounds were tested for antibacterial activity and showed good efficacy against two gram-positive bacteria (<i>Streptococcus pyogenes</i> and <i>Staphylococcus aureus</i>) and two gram-negative bacteria (<i>Escherichia coli</i> and <i>Proteus mirabilis</i>). The docking study suggested substantial overlap between the ligand and protein active site compared to the reference drug (ibuprofen).</p>