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

Molecules

A. A. Jarrahpour¹  M. Shekarriz¹ 

[1] Chemistry Department, College of Sciences, Shiraz University, Shiraz 71454, Iran. Tel.: [phone], Fax: [phone]

关键词: Monocyclic sugar-based β-lactam;    galactose;    Schiff base;    phthalimidoacetyl chloride;    antimicrobial activity;   

DOI  :  10.3390/90100029

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
© 2004 by MDPI (http://www.mdpi.org).