umu.sePublikasjoner
Endre søk
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Design and Parallel Solid Phase Synthesis of Ring Fused 2-Pyridinones that Target Pilus Biogenesis in Pathogenic Bacteria
Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
Vise andre og tillknytning
2002 (engelsk)Inngår i: Journal of Combinatorial Chemistry, Vol. 4, s. 630-639Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

A new method for the solid-phase synthesis of enantiomerically enriched highly substituted ring-fused 2-pyridinones 13 has been developed. The synthesis mediates introduction of substituents at two positions in the 2-pyridinone ring in a diverse manner and is suitable for parallel synthesis. 19F NMR spectroscopy was used as a tool to monitor each of the five steps in the reaction sequence. The optimized conditions thus obtained were then used to prepare a library of 20 2-pyridinones with high yields. The library members were chosen from a statistical multivariate design to ensure diversity and reliable data for structure−activity relationships. Screening of the library against the bacterial periplasmic chaperone PapD was performed using surface plasmon resonance. Three new 2-pyridinones with a higher affinity for the chaperone PapD than the previous best 13{10,1} were found, and important structural features could be deduced.

sted, utgiver, år, opplag, sider
2002. Vol. 4, s. 630-639
Identifikatorer
URN: urn:nbn:se:umu:diva-3203DOI: 10.1021/cc020032dOAI: oai:DiVA.org:umu-3203DiVA, id: diva2:141702
Tilgjengelig fra: 2003-11-28 Laget: 2003-11-28 Sist oppdatert: 2018-06-09bibliografisk kontrollert
Inngår i avhandling
1. Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
2003 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Umeå: Department of Chemistry, Organic Chemistry, Umeå University, 2003. s. 75
Emneord
Organic chemistry, β-lactam, 2-pyridinone, 2-pyridone, Meldrum’s acid, Δ2-thiazoline, solid-phase synthesis, microwave assisted synthesis, antibacterial, pili, pilicide, Organisk kemi
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:umu:diva-165 (URN)91-7305-546-8 (ISBN)
Disputas
2003-12-19, Stora Hörsalen, KBC-huset,, Umeå universitet, Umeå, 13:00 (engelsk)
Opponent
Tilgjengelig fra: 2003-11-28 Laget: 2003-11-28 Sist oppdatert: 2018-03-15bibliografisk kontrollert

Open Access i DiVA

Fulltekst mangler i DiVA

Andre lenker

Forlagets fulltekst

Personposter BETA

Almqvist, Fredrik

Søk i DiVA

Av forfatter/redaktør
Almqvist, Fredrik
Av organisasjonen

Søk utenfor DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric

doi
urn-nbn
Totalt: 98 treff
RefereraExporteraLink to record
Permanent link

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