Antibacterially Active Substituted Anilides of Carboxylic and Sulfonic Acids

Article abstract of DOI:10.1021/jm00366a016

Anilides of carboxylic and sulfonic acids were prepared and tested for antimicrobial activity.While these anilides were ineffective against Gram-negative organisms, there was good correlation between chemical structure and biological activity against Gram-positive species.Both the nature and position of the benzene ring substituents and the length of the carbon side chain affected the activity and specificity of the compounds.The highest activity was observed when the acyl or sulfuryl moiety had a C7-C9 side chain attached.The CONH and SO2NH bridging groups wereequally effective.The attachment of COOH or COOCH3 groups in the ω-position did not effect activity, but the substitution of the acidic proton of the sulfonamide group by an alkyl group rendered the compound inactive.Six compounds, which were substituted anilides of sulfonic acids, fatty acids, or the analogues α-methylene-substituted acids, were bacteriostatic at 10 ppm against Bacillus cereus, Staphylococcus aureus, Streptococcus faecalis and Lactobacillus plantarum .One of these compounds, 2-hydroxy-5-nitroanilide of α-methylenedecanoic acid, was bactericidal at 1 ppm.