Synthesis and antimicrobial activity of some new sugar-based monocyclic beta-lactams.
The syntheses of some new sugar-based monocyclic beta-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 beta-lactam 6 as a single isomer. Treatment of protected beta-lactams 6 and 8 with methylhydrazine afforded the free amino beta-lactams 9 and 10. Acylation of these free amino beta-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded beta-lactams 11a-d and 12a-d. Some of these novel beta-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis.
Jarrahpour
A A
AA
Chemistry Department, College of Sciences, Shiraz University, Shiraz 71454, Iran. jarrah@susc.ac.ir
Shekarriz
M
M
Taslimi
A
A
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D002241:Carbohydrates / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry; D006801:Humans; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D008997:Monobactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D000900:Anti-Bacterial Agents; D002241:Carbohydrates; D008997:Monobactams; D005690:Galactose