SYNTHESIS OF 3-ACETOXYAZETIDIN-2-ONES AND 3-HYDROXYAZETIDIN-2-ONES WITH ANTIFUNGAL AND ANTIBACTERIAL ACTIVITY

The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydro xyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-a cetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substitut ed Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7 oxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and oxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtai ned. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candi da albicans, Candida tropicalis, Candida parapsilosis, Candida glabrat a, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h con taining a free carboxylic acid group on the N-1 aryl ring displayed an tibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Es cherischia coli.