Our previous studies on antituberculosis agents resulted in synthesis of 2-pyrazinecarbamoildithiocarbazate acid esters and amides and also acethylpyrazine thiosemicarbazone derivatives with various tuberculostatic activity [1,2]. Continuing those studies we have synthesized of N’-(6-methoxypyrazin-2-carbonyl)dithiocarbazic acid esters and their amidrazone analogs. Acid hydrolysis of methyl 6-methoxypyrazine-2-carbimidate 1 led to methyl ester 2 while treatment with hydrazine hydrate afforded amidrazone 3. Ester 2 applied to the reaction with hydrazine hydrate or methylhydrazine gave corresponding hydrazides 4,5 which when treated with carbon disulfide and appropriate halides in the presence of triethylamine reacted giving N’-(6-methoxypyrazine-2-carbonyl)dithiocarbazic acid esters 6-26. Similar reactions performed for amidrazone 3 resulted with corresponding structural analogs 29-33.

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] C. Orlewska, H. Foks, M. Janowiec, Z. Zwolska-Kwiek: Pharmazie 50 (1995) 565-566.
[2] B. Milczarska, H. Foks, Z. Trapkowski, A. Milżyńska-Kołaczek, M. Janowiec, Z. Zwolska, Z. Andrzejczyk: Acta Pol. Pharm. – Drug Res. 55 (1998) 289-295.

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