原创力文档synthesis and antimicrobial activity of some new sugar-based monocyclic β-lactams合成及抗菌活性的一些新的糖基单环β-lactams.pdfVIP
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synthesis and antimicrobial activity of some new sugar-based monocyclic β-lactams合成及抗菌活性的一些新的糖基单环β-lactams
Molecules 2004, 9, 29-38
molecules
ISSN 1420-3049
/
Synthesis and Antimicrobial Activity of Some New Sugar-Based
Monocyclic β-Lactams
A. A. Jarrahpour 1,*, M. Shekarriz 1 and A. Taslimi 2
1 Chemistry Department, College of Sciences, Shiraz University, Shiraz 7 1454, Iran. Tel.: +98 711 228
4822, Fax: +98 711 228 0926.
2 Institute of Standards and Industrial Research of Iran, Shiraz 71447, Iran.
* Author to whom correspondence should be addressed; e-mail: jarrah@susc.ac.ir;
aliasghar6683@
Received: 14 June 2003; in revised form: 22 August 2003 / Accepted: 7 September 2003 / Published:
31 January 2004
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, phthalimidoace
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