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Molecules 2004, 9(1), 29-38; doi:10.3390/90100029
Article

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

1,* , 1 and 2
1 Chemistry Department, College of Sciences, Shiraz University, Shiraz 71454, Iran 2 Institute of Standards and Industrial Research of Iran, Shiraz 71447, Iran
* Author to whom correspondence should be addressed.
Received: 14 June 2003 / Revised: 22 August 2003 / Accepted: 7 September 2003 / Published: 31 January 2004
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Abstract

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.
Keywords: Monocyclic sugar-based β-lactam; galactose; Schiff base; phthalimidoacetyl chloride; antimicrobial activity. Monocyclic sugar-based β-lactam; galactose; Schiff base; phthalimidoacetyl chloride; antimicrobial activity.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Jarrahpour, A.A.; Shekarriz, M.; Taslimi, A. Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams. Molecules 2004, 9, 29-38.

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