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Efficient Microwave Assisted Synthesis of Optically Active Bicyclic 2-Pyridinones via Δ2-Thiazolines
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2003 (English)In: Molecular diversity, ISSN 1381-1991, E-ISSN 1573-501X, no 2-4, 165-169 p.Article in journal (Refereed) Published
Abstract [en]

A new efficient synthesis of optically active bicyclic 2-pyridiones has been developed using microwave irradiation. The synthesis is a two-step procedure via 2-thiazolines, which only requires a 3 + 2 min reaction time compared to 2 days when using conventional heating. The optimized conditions proved to be suitable for the synthesis of a small library in excellent yields and with limited racemizations.

Place, publisher, year, edition, pages
Springer Netherlands, 2003. no 2-4, 165-169 p.
Keyword [en]
cycloaddition, Meldrum's acid, microwave, pyridone, thiazoline, 2-pyridinone
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-3204DOI: 10.1023/B:MODI.0000006800.46154.99OAI: oai:DiVA.org:umu-3204DiVA: diva2:141703
Available from: 2003-11-28 Created: 2003-11-28 Last updated: 2012-06-14Bibliographically approved
In thesis
1. Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
Open this publication in new window or tab >>Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
2003 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

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.

Place, publisher, year, edition, pages
Umeå: Department of Chemistry, Organic Chemistry, Umeå University, 2003. 75 p.
Keyword
Organic chemistry, β-lactam, 2-pyridinone, 2-pyridone, Meldrum’s acid, Δ2-thiazoline, solid-phase synthesis, microwave assisted synthesis, antibacterial, pili, pilicide, Organisk kemi
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-165 (URN)91-7305-546-8 (ISBN)
Public defence
2003-12-19, Stora Hörsalen, KBC-huset,, Umeå universitet, Umeå, 13:00 (English)
Opponent
Available from: 2003-11-28 Created: 2003-11-28 Last updated: 2012-05-15Bibliographically approved

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