Functionalization of bicyclic 2-pyridones targeting pilus biogenesis in uropathogenic Escherichia coli
2007 (German)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 48, no 26, 4543-4546 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
Oxford: Pergamon Press , 2007. Vol. 48, no 26, 4543-4546 p.
2-Pyridone, Formylation, Antibacterial agent, Pilicide, Biofilm inhibitor
IdentifiersURN: urn:nbn:se:umu:diva-2713DOI: 10.1016/j.tetlet.2007.04.142OAI: oai:DiVA.org:umu-2713DiVA: diva2:140962