Planarity of heteroaryldithiocarbazic acid derivatives showing tuberculostatic activity: structure–activity relationships

Abstract

The search for new tuberculostatics is an important issue due to the increasing resistance ofMycobacterium tuberculosisto existing agents and the resulting spread of the pathogen. Heteroaryldithiocarbazic acid derivatives have shown potential tuberculostatic activity and investigations of the structural aspects of these compounds are thus of interest. Three new examples have been synthesized. The structure of methyl 2-[amino(pyridin-3-yl)methylidene]hydrazinecarbodithioate, C8H10N4S2, at 293 K has monoclinic (P21/n) symmetry. It is of interest with respect to antibacterial properties. The structure displays N—H...N and N—H...S hydrogen bonding. The structure ofN′-(pyrrolidine-1-carbonothioyl)picolinohydrazonamide, C11H15N5S, at 100 K has monoclinic (P21/n) symmetry and is also of interest with respect to antibacterial properties. The structure displays N—H...S hydrogen bonding. The structure of (Z)-methyl 2-[amino(pyridin-2-yl)methylidene]-1-methylhydrazinecarbodithioate, C9H13N4S2, has triclinic (P\overline{1}) symmetry. The structure displays N—H...S hydrogen bonding.