Synthesis and tuberculostatic activity of novel N'-methyl-4-(pyrrolidin-1-yl)picolinohydrazide and N'-methylpyrimidine-2-carbohydrazide derivatives

The synthesis of N'-methyl-4-(pyrrolidin-1-yl)picolinohydrazide and N'-methyl-pyrimidine-2-carbohydrazide derivatives (5a and 5b) was carried out. These compounds were used as starting materials to obtain methyl N'-methylhydrazinecarbodithioates 6a and 6b, which, on reaction with either triethylamine or hydrazine, gave corresponding 1,3,4-oxadiazioles 7a and 7b or 1,2,4-triazoles 9a and 9b with the free NH2 group at the N-4 position, respectively. Compounds 8ae, particularly containing cyclic amines at N-4 of the 1,2,4-triazole ring, were also obtained. Synthesized compounds were tested in vitro for their activity against Mycobacterium tuberculosis. The structureactivity relationship analysis for obtained compounds was done. (C) 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:223230, 2012; View this article online at . DOI 10.1002/hc.21008