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

• 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.

Nyckelord

2-Pyridone

Formylation

Antibacterial agent

Pilicide

Biofilm inhibitor

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ref (ämneskategori)

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