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Efficient Microwave Assisted Synthesis of Optically Active Bicyclic 2-Pyridinones via Δ2-Thiazolines
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
2003 (Engelska)Ingår i: Molecular diversity, ISSN 1381-1991, E-ISSN 1573-501X, nr 2-4, s. 165-169Artikel i tidskrift (Refereegranskat) 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.

Ort, förlag, år, upplaga, sidor
Springer Netherlands, 2003. nr 2-4, s. 165-169
Nyckelord [en]
cycloaddition, Meldrum's acid, microwave, pyridone, thiazoline, 2-pyridinone
Nationell ämneskategori
Kemi
Identifikatorer
URN: urn:nbn:se:umu:diva-3204DOI: 10.1023/B:MODI.0000006800.46154.99OAI: oai:DiVA.org:umu-3204DiVA, id: diva2:141703
Tillgänglig från: 2003-11-28 Skapad: 2003-11-28 Senast uppdaterad: 2018-06-09Bibliografiskt granskad
Ingår i avhandling
1. Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
Öppna denna publikation i ny flik eller fönster >>Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
2003 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Umeå: Department of Chemistry, Organic Chemistry, Umeå University, 2003. s. 75
Nyckelord
Organic chemistry, β-lactam, 2-pyridinone, 2-pyridone, Meldrum’s acid, Δ2-thiazoline, solid-phase synthesis, microwave assisted synthesis, antibacterial, pili, pilicide, Organisk kemi
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:umu:diva-165 (URN)91-7305-546-8 (ISBN)
Disputation
2003-12-19, Stora Hörsalen, KBC-huset,, Umeå universitet, Umeå, 13:00 (Engelska)
Opponent
Tillgänglig från: 2003-11-28 Skapad: 2003-11-28 Senast uppdaterad: 2018-03-15Bibliografiskt granskad

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Totalt: 244 träffar
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