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Design and Parallel Solid Phase Synthesis of Ring Fused 2-Pyridinones that Target Pilus Biogenesis in Pathogenic Bacteria
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- Emtenäs, Hans (author)
- Umeå universitet,Kemiska institutionen
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- Åhlin, Kristoffer (author)
- Umeå universitet,Kemiska institutionen
- Pinkner, Jerome S. (author)
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- Hultgren, Scott J. (author)
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- (creator_code:org_t)
- 2002-10-05
- 2002
- English.
- In: Journal of Combinatorial Chemistry. - : American Chemical Society (ACS). - 1520-4766 .- 1520-4774. ; 4, s. 630-639
- Journal article (peer-reviewed)
Abstract
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- 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.
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