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Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones : Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria

New methods have been developed for the synthesis of bicyclic β-lactams and 2-pyridinones by combining acyl Meldrum’s acids and Δ2-thiazolines. The 2-pyridinones were synthesised both in solution using conventional heating or microwave assisted heating as well as by solid supported chemistry. The compounds (pilicides) were designed to interfere with the assembly of pili in uropathogenic E. coli by inhibiting the periplasmic chaperones. The affinity of the pilicides to the chaperones was investigated with surface plasmon resonance technique (Biacore) and with relaxation-edited 1H NMR spectroscopy experiments. Finally, the pilicides were investigated for their ability to inhibit pili formation in uropathogenic E. coli in a hemagglutination assay, where members of the 2-pyridinone family proved to be able to cause depiliation.

Identiferoai:union.ndltd.org:UPSALLA1/oai:DiVA.org:umu-165
Date January 2003
CreatorsEmtenäs, Hans
PublisherUmeå universitet, Kemiska institutionen, Umeå : Department of Chemistry, Organic Chemistry, Umeå University
Source SetsDiVA Archive at Upsalla University
LanguageEnglish
Detected LanguageEnglish
TypeDoctoral thesis, comprehensive summary, info:eu-repo/semantics/doctoralThesis, text
Formatapplication/pdf
Rightsinfo:eu-repo/semantics/openAccess

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