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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
Received: 14 June 2003; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Jarrahpour, A.A.; Shekarriz, M.; Taslimi, A. Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams. Molecules 2004, 9, 29-38.

AMA Style

Jarrahpour AA, Shekarriz M, Taslimi A. Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams. Molecules. 2004; 9(1):29-38.

Chicago/Turabian Style

Jarrahpour, A. A.; Shekarriz, M.; Taslimi, A. 2004. "Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams." Molecules 9, no. 1: 29-38.



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