umu.sePublikationer
Ändra sökning
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
An Enantioselective Ketene-Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
2001 (Engelska)Ingår i: The Journal of Organic Chemistry, Vol. 66, nr 20, s. 6756-61Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Previously, a method for the stereoselective synthesis of -lactams, starting from 2H-2-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-2-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 78 C. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 64 C led to the desired 2-pyridinones in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different 2-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.

Ort, förlag, år, upplaga, sidor
2001. Vol. 66, nr 20, s. 6756-61
Nationell ämneskategori
Kemi
Identifikatorer
URN: urn:nbn:se:umu:diva-9584DOI: doi:10.1021/jo015794uOAI: oai:DiVA.org:umu-9584DiVA, id: diva2:149255
Tillgänglig från: 2008-04-28 Skapad: 2008-04-28 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

Open Access i DiVA

Fulltext saknas i DiVA

Övriga länkar

Förlagets fulltext

Personposter BETA

Almqvist, Fredrik

Sök vidare i DiVA

Av författaren/redaktören
Almqvist, Fredrik
Av organisationen
Kemiska institutionen
Kemi

Sök vidare utanför DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetricpoäng

doi
urn-nbn
Totalt: 143 träffar
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf