Functionalization of bicyclic 2-pyridones targeting pilus biogenesis in uropathogenic Escherichia coli

Nils Pemberton, Jerome S. Pinkner, Jennifer M. Jones, Lotta Jakobsson, Scott J. Hultgren, Fredrik Almqvist

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Substituted bicyclic 2-pyridones, termed pilicides, prevent pilus assembly in uropathogenic Escherichia coli. Based on the bioactive methyl ester protected 2-pyridone 4, further functionalization at C-6 has yielded a set of new compounds, which have been evaluated for their ability to inhibit pilus formation in uropathogenic E. coli. The key intermediate in the synthesis was formylated 2-pyridone 5, which could be obtained via a Vilsmeier reaction. This versatile intermediate was converted into secondary and tertiary amines via reductive amination and could also be converted to other interesting functionalities using simple chemical transformations.

Original languageEnglish
Pages (from-to)4543-4546
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number26
DOIs
StatePublished - Jun 25 2007

Keywords

  • 2-Pyridone
  • Antibacterial agent
  • Biofilm inhibitor
  • Formylation
  • Pilicide

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