Synthesis, Characterization and Evaluation of Antimicrobial Properties of (R)-(-)-4-Phenyl-2 Oxazolidinone Based Azetidinones

Introduction: A series of (R)-(-)-4-Phenyl-2 oxazolidinone based azetidinones (4a-i) were synthesized from the reaction of (2-Oxo-4-phenyl-oxazolidin-3-yl) acetic acid with aromatic imines (3a-i) in the presence of Thionyl chloride and Triethylamine as a base. Methods: The transformation proceeds through the formation of acid chloride to ketene which finally forms the azetidinones through [2+2] cycloaddition with aromatic imines. Products obtained were screened to evaluate their antibacterial activity with respect to known bacteria like Escherichia Coli (E. Coli) and Bacillus subtilis. Results and Conclusion: In most of the cases, azetidinones were found to exhibit superior antimicrobial properties than oxazolidinones. They were found to be a good inhibitor of gram-positive and gramnegative bacteria. Enhancement of antibacterial property can be attributed to the presence of azetidinone ring and hydrophobic alkyl side chain in the scaffolds.