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Short Paper | Regular issue | Vol 85, No. 9, 2012, pp.2269-2280
Published online, 13th July, 2012
DOI: 10.3987/COM-12-12524
Synthesis, Characterization, and Tuberculostatic Activity of Novel Heterocyclic Compounds Derived from Dimethyl Heteroaroylcarbonohydrazonodithioates

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 dimethyl heteroaroylcarbonohydrazonodithioates (1-5) has been synthesized from various heterocyclic carbohydrazides. N'-(Cycloalkyldiamin-2-ylidene)heteroaroylhydrazides (9-20) were obtained by the substitution of dimethyl heteroaroylcarbonohydrazonodithioates with respective diamines in EtOH or dioxane. In water the substitution was followed by cyclization to 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidines (21-23). The compounds obtained were tested in vitro towards M. tuberculosis standard strain (H37Rv) and two “wild” strains, susceptible (Spec. 192) and resistant (Spec. 210). MIC values for all the compounds tested were within 25-100 µg/mL which indicated their activity lower than reference drugs used (INH, PZA).