Synthesis of sulfanilamido-naphthoquinones as potential antituberculous agents

Article abstract of DOI:10.1002/jps.2600720116

p-Aminobenzoic acid, the acid hydrazides of benzoic acid, salicylic acid and isonicotinic acid, and 4,4'-diaminodiphenyl sulfone were condensed with p-aminobenzenesulfonyl chloride to give the corresponding N₁-substituted sulfanilamides. These molecules were then treated with 1,4-naphthoquinone to yield 2-substituted-1,4-naphthoquinones. The partition coefficient for the substituted quinones showed, in some cases, high diffusion rates to the organic phase, benzene, from physiological Tyrode's solution. These compounds are effective in low concentration in dioxane against the human sensitive strain of Mycobacterium tuberculosis H₃₇ Rv. Sulfanilamides obtained from p-aminosalicylic acid and thiosemicarbazide failed to react with 1,4-naphthoquinone. These sulfanilamides also showed high activity against the same Mycobacterium.