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Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams

Author(s): A. A. Jarrahpour | M. Shekarriz | A. Taslimi

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 1;
Start page: 29;
Date: 2004;
Original page

Keywords: Monocyclic sugar-based β-lactam | galactose | Schiff base | phthalimidoacetyl chloride | antimicrobial activity.

The syntheses of some new sugar-based monocyclic β-lactams possessing several other functionalities in addition to the carbohydrate moiety are described. The key step was the Staudinger [2+2] cycloaddition of chiral carbohydrate Schiff base 5 with phthalimidoacetyl chloride to yield the sugar-based monocyclic β-lactam 6 as a single isomer. Treatment of protected β-lactams 6 and 8 with methylhydrazine afforded the free amino β-lactams 9 and 10. Acylation of these free amino β-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded β-lactams 11a-d and 12a-d. Some of these novel β-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis.
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