Synthesis and evaluation of dihydroimidazolo and dihydrooxazolo ring-fused 2-pyridones—targeting pilus biogenesis in uropathogenic bacteria

N Pemberton, JS Pinkner, S Edvinsson, SJ Hultgren…

Index: Pemberton, Nils; Pinkner, Jerome S.; Edvinsson, Sofie; Hultgren, Scott J.; Almqvist, Fredrik Tetrahedron, 2008 , vol. 64, # 40 p. 9368 - 9376

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Citation Number: 17

Abstract

Dihydrothiazolo ring-fused 2-pyridones have previously been shown to inhibit pilus assembly in uropathogenic Escherichia coli. Methods have now been developed to synthesize both dihydroimidazolo and dihydrooxazolo ring-fused 2-pyridones. To obtain the nitrogen analogs, Cbz-protected imidazolines were reacted with an acyl-Meldrum's acid derivative under acidic conditions. To prepare the oxygen analogs, a one-pot procedure ...