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Paper | Regular issue | Vol 81, No. 4, 2010, pp.917-934
Published online, 19th February, 2010
DOI: 10.3987/COM-09-11888
Synthesis and Tuberculostatic Activity of Novel 1,2,4-Triazoles Obtained from Heterocyclic Carbohydrazides

Katarzyna Gobis,* Henryk Foks, Zofia Zwolska, and Ewa Augustynowicz-Kopeć

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

Abstract

The novel 1,2,4-triazole derivatives have been synthesized by a few different pathways. Heterocyclic carbohydrazides were used to obtain monoesters of hydrazine acids (1-6), thiosemicarbazide derivatives (7-17), and finaly 1,2,4-triazole-5-thiones (18-38). Carbohydrazides were also cyclized with methyl carbamodithioates in the presence of DBU giving 1,2,4-triazole-5-thiones (18, 19, 39-47). Two of final products (39, 40) were undergone alkylation in alkaline solution to appropriate sulfides (48-53). Then methylsulfides (48, 49) were oxidized with peroxyacetic acid to sulfoxides (54, 55). The obtained compounds were tested in vitro towards Mycobacterium tuberculosis.