Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones

Abstract 4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl β-aminocrotonates with dialkyl malonates or ‘magic malonates’ (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8 μg/ml). A structure-activity relationship is discussed.