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

Acta Crystallogr C Struct Chem. 2018 Mar 1;74(Pt 3):400-405. doi: 10.1107/S205322961800284X. Epub 2018 Feb 28.

Abstract

The search for new tuberculostatics is an important issue due to the increasing resistance of Mycobacterium tuberculosis to 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 of N'-(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-1) symmetry. The structure displays N-H...S hydrogen bonding.

Keywords: Mycobacterium tuberculosis; antibacterial activity; crystal structure; heteroaryldithiocarbazic acid; structure–activity relationship; tuberculostatic.

MeSH terms

  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Mycobacterium tuberculosis / chemistry*
  • Structure-Activity Relationship

Substances

  • Antitubercular Agents