CHEMOTHERAPEUTIC NITROHETEROCYCLES . DERIVATIVES OF 5-NITROTHIAZOLE-2-CARBOXALDEHYDE AND 5-NITROTHIAZOLE-2-CARBOXYLIC ACID

A series of new 5-nitrothiazoles bearing carbon substituents in the 2 position has been prepared. Treatment of 2-bromo-5-nitrothiazole with CuCN provided 5-nitrothiazole-2-carbonitrile, a key intermediate for subsequent conversion to other derivatives of 5-nitrothiazole-2-carboxylic acid. The corresponding aldehyde was obtained by condensing 2-methl,-5-nitrothiazole with benzaldehyde and oxidatively cleaving the resulting styryl intermediate. The compounds prepared in this study were evaluated in vivo for antimalarial and antischistosomal activity and in vitro for activity against bacteria, yeast, and a fungus. Little activity was noted in the malaria and schistosomiasis tests, but broad-spectrum inhibitory effects were widely evident in the in vitro assays. The most potent compound, 5-nitrothiazole-2-carboxaldehyde acethvdrazone, was inhibitory at 1 μg/ml or less in all but one of the latter tests. © 1969, American Chemical Society. All rights reserved.