In this work, several oxadiazole, thiadiazole, and triazole derivatives, as well as new Schiff bases, were prepared. Cholic acid was used as a starting material to prepare the five-membered heterocyclic compounds. The synthesized compounds were identified by FTIR and 1H,13C-NMR spectroscopy, which elucidated and confirmed the structure of the target molecules. Estimation of the biological activity of the newly produced compounds has been conducted against two types of Gram-positive and Gram-negative pathogenic bacteria.