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

Author(s): Shyamal Baruah, Amrit Puzari*, Farhana Sultana, Jayanta Barman.

Journal Name: Anti-Infective Agents
Anti-Infective Agents in Medicinal Chemistry

Volume 16 , Issue 2 , 2018

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Graphical 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.

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Article Details

Year: 2018
Page: [104 - 113]
Pages: 10
DOI: 10.2174/2211352516666180619153317
Price: $25

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