Bilingual day care in Zurich Kinderkrippe Zürich
Kinderbetreuung in Zürich Kinderkrippe Zürich
Kita in Zürich Kinderkrippe Zürich
Kinderkrippe in Zürich Seebach Kinderkrippe Seebach
Academic Journals Database
disseminating
quality controlled scientific knowledge



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.

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.