Antimycobacterial activity of some quinolyl aryl sulfides, sulfones, and ethers, in vitro

A series of 61 compounds of six different categories (nitrosulfides, nitrosulfones, aminosulfides, aminosulfones, nitroethers, and aminoethers), all heterocyclic analogues of diaminodiphenyl sulfone (DADS), were synthesized by replacing one of the benzene rings of DADS by a 5-nitro-quinoline ring and the other benzene ring by various heterocyclic nuclei. Among these compounds, 51 were found to inhibit the growth of Mycobacterium tuberculosis at a concentration of 40 mug or less per ml; 8 compounds were effective at a concentration of 1 mug/ml and 9 were effective at a concentration of 0.1 mug/ml. 5-Amino-8-quinolyl-2,4-dichlorophenyl sulfide was found to be 20 times more effective than isonicotinic acid hydrazide and 80 times more effective than streptomycin.