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-hydroxyazetidin-2-ones 6a–j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a–h which possess a free carboxylic acid group on the N-1 aryl rin...

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Bibliographic Details
Published in:	European journal of medicinal chemistry Vol. 31; no. 12; pp. 989 - 1000
Main Authors:	Walsh, OM, Meegan, MJ, Prendergast, RM, Al Nakib, T
Format:	Journal Article
Language:	English
Published:	Oxford Elsevier Masson SAS 1996 Elsevier
Subjects:	3-acetoxyazetidin-2-one 3-hydroxyazetidin-2-one antibacterial activity Antibiotics. Antiinfectious agents. Antiparasitic agents antifungal activity Antifungal agents Biological and medical sciences Medical sciences Pharmacology. Drug treatments antibacterial activity 3-acetoxyazetidin-2-one 3-hydroxyazetidin-2-one antifungal activity Antifungal agent Four membered ring Structure activity relation Carboxylic acid Nitrogen heterocycle Benzene derivatives Lactam Antibacterial agent Chemical synthesis In vitro
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Summary:	The synthesis of a series of 3-acetoxyazetidin-2-ones 3a–n and 3-hydroxyazetidin-2-ones 6a–j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a–h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a–h with acetoxyacetyl chloride. The novel bicyclic structures 7-acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a–h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.
ISSN:	0223-5234 1768-3254
DOI:	10.1016/S0223-5234(97)86178-8