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Paper | Regular issue | Vol 85, No. 4, 2012, pp.871-885
Published online, 28th February, 2012
DOI: 10.3987/COM-12-12436
Synthesis and Tuberculostatic Activity of Novel Diverse Heterocyclic Compounds Derived from Heterocyclic Carbohydrazides and Methyl 2-Heteroaroylhydrazinecarbodithioates

Katarzyna Gobis,* Henryk Foks, Ewa Augustynowicz-Kopeć, and Agnieszka Napiórkowska

*Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, Poland

Abstract

A series of 1,3,4-oxadiazole-2-thiones (4, 5), 2-methylthio-1,3,4-thiadiazoles (15, 16) and 1,2,4-triazole-3-thiones (17-32) have been synthesized using high reactivity of various methyl 2-heteroaroylhydrazinecarbodithioates, that underwent cyclization in alkaline or acidic solution. Reaction of 4-(2-(methylthiocarbonothioyl)hydrazine) carbonyl)pyridine 1-oxide with morpholine led to 4-(5-morpholino-1,3,4-oxadiazol-2-yl)pyridine 1-oxide (11). 2-Methylthio-1,3,4-oxadiazoles (12-14) were obtained by the methylation of 1,3,4-oxadiazole-2-thiones (1, 4, 5) in alkaline solution. 1,2,4-Triazole-3-thiones (21-23, 31) obtained in reaction with aminoalcohols gave 1,2,4-triazolo[3,4-b][1,3]thiazines when refluxed in conc. HCl. The obtained compounds were tested in vitro towards Mycobacterium tuberculosis standard strain (H37Rv) and two “wild” strains, susceptible (Spec. 192) and resistant (Spec. 210).