The 1,2,4-oxadiazole is a heterocycle which has seen utility in producing bioactive compounds extensively used in many research programs. Among others some 1,2,4-oxadiazole derivatives are known as antibacterial agents active against Mycobacterium tuberculosis.¹

Our previous studies on antituberculosis agents resulted in synthesis of 3-pyrazine-1,2,4-oxadiazoles with high tuberculostatic activity even against resistant strains. ² That fact prompted us to synthesize a series of new disubstituted 1,2,4-oxadiazoles bearing pyrazine or pyridine ring in 3-position and amine or amide functional group in 5-position. The amides were obtained from appropriate amidoximes in reaction with carbamoyl chlorides. Some of the amides have undergone thermal decarboxylation to tertiary amines. All reactions were performed according to the following scheme:

The structures of novel compounds were confirmed by IR, ¹H NMR and MS spectra. The tuberculostatic activity was tested using M. tuberculosis strain H₃₇Rv and wild strains isolated from tuberculotic patients and resistant to common applied antituberculosis drugs.

References:

1. M. H. Gezginici, A. R. Martin, S. G. Franzblau: J. Med. Chem. 44 (2001)1560-1563.
2. D. Pancechowska-Ksepko, H. Foks, M. Janowiec, Z. Zwolska-Kwiek: Acta Polon. Pharm. 33 (1986) 211-217.

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