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

[ Vol. 16 , Issue. 2 ]

Author(s):

Shyamal Baruah, Amrit Puzari*, Farhana Sultana and Jayanta Barman   Pages 104 - 113 ( 10 )

Abstract:


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.

Keywords:

(R)-(-)-4-Phenyl-2-oxazolidinone, Azetidinone, Antibacterial, Drug-resistant, Gram-positive, Gram-negative.

Affiliation:

Department of Chemistry, National Institute of Technology Nagaland, Chumukedima, Dimapur, Nagaland, Department of Chemistry, National Institute of Technology Nagaland, Chumukedima, Dimapur, Nagaland, Department of Physics, ADP College, Nagaon, Nagaon, Assam, Department of Physics, ADP College, Nagaon, Nagaon, Assam

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