Four azole derivatives of proline, namely 2-[2-( 1,3,4-oxadiazol-5-thionyl)]proline 5, 2-[2-( 4-N-amino-1,2,4- triazol-5-thiolyl)] proline 6, 2-[2-(1,2,4-triazol-5-thiolyl)] proline 7 and 2-[2-( 1,3,4-thiadiazol-5-thionyl)] proline 8 have been synthesized from proline 1via a common synthetic pathway. IR, 1H-NMR, 13C-NMR and DEPT-NMR, characterized all intermediates and final products. The antibacterial activities assessed using the paper disk diffusion method against Gram-negative bacteria: Pseudomonas aeruginosa and Escherichia coli and Grampositive bacteria, Bacillus cereus, and Staphylococcus aureus. Some of the synthetic compounds showed promising activity against microorganisms under test in comparison to commercially available antibiotics ampicillin and gentamycin.