Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic ÃŽÂ²-LactamsAuthor(s): A. A. Jarrahpour | M. Shekarriz | A. Taslimi
Journal: Molecules ISSN 1420-3049
Volume: 9; Issue: 1; Start page: 29; Date: 2004;
Keywords: Monocyclic sugar-based ÃŽÂ²-lactam | galactose | Schiff base | phthalimidoacetyl chloride | antimicrobial activity.
The syntheses of some new sugar-based monocyclic ÃŽÂ²-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 ÃŽÂ²-lactam 6 as a single isomer. Treatment of protected ÃŽÂ²-lactams 6 and 8 with methylhydrazine afforded the free amino ÃŽÂ²-lactams 9 and 10. Acylation of these free amino ÃŽÂ²-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded ÃŽÂ²-lactams 11a-d and 12a-d. Some of these novel ÃŽÂ²-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis.