Collect. Czech. Chem. Commun. 1990, 55, 307-316

Antimycobacterial thiobenzanilides

Karel Waissera, Nestor Houngbedjia, Miloš Macháčeka, Miroslav Sekeraa, Josef Urbana and Želmíra Odlerováb

a Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 501 65 Hradec Králové
b Research Institute of Preventive Medicine, 833 01 Bratislava


A group of 30 thiobenzanilides active against Mycobacterium kansasii have been synthesized and their 1H NMR and UV spectra and RM values (TLC on silica gel impregnated with methylsilicone oil) have been measured. From the correlation between the chemical shifts of the thioamide proton in the 1H NMR spectra and the Hammett constants it can be concluded that the substituents in both aromatic rings uniformly affect the electron density of the thioamide group. The antimycobacterial activity is probably connected with local molecular parameters and can be considered to be approximately additive with respect to both parts of the molecule.