Skip to main content
padlock icon - secure page this page is secure

Planarity of heteroaryldithiocarbazic acid derivatives showing tuberculostatic activity. III. Mono‐ and diesters of 3‐(pyrazin‐2‐ylcarbonyl)dithiocarbazic acid

Buy Article:

$52.00 + tax (Refund Policy)

Methyl 2‐(pyrazin‐2‐ylcarbonyl)hydrazinecarbodithioate, C7H8N4OS2, (E1), N′‐[bis(methylsulfanyl)methylidene]pyrazine‐2‐carbohydrazide, C8H10N4OS2, (F1), N′‐[bis(methylsulfanyl)methylidene]‐6‐methoxypyrazine‐2‐carbohydrazide, C9H12N4O2S2, (F2), and methyl 1‐methyl‐2‐(pyrazin‐2‐ylcarbonyl)hydrazinecarbodithioate, C8H10N4OS2, (G1), can be considered as derivatives of classical (thio)amide‐type tuberculostatics, and all are moderately active against Mycobacterium tuberculosis. This study was undertaken in a search for relationships between activity and specific intramolecular interactions, especially conjugations and hydrogen‐bond contacts, and the molecular structures were compared with respective amine analogues, also active against the pathogen. Despite the differences between the amine and carbonyl groups with opposite functions in the hydrogen bond, the two types of structure show a surprisingly similar planar geometry, mostly due to the conjugations aided by the bifurcated intramolecular hydrogen‐bond contact between the N—H group of the central hydrazide group as donor and a pyrazine N atom and an S atom of the dithio function as acceptors. Planarity was suggested to be crucial for the tuberculostatic activity of these compounds. The N‐methylated derivative (G1) showed a significant twist at the N—N bond [torsion angle = −121.9 (3)°] due to the methyl substitution, which precludes an intramolecular N—H...S contact and the planarity of the whole molecule. Nonetheless, the compound shows moderate tuberculostatic activity.
No References
No Citations
No Supplementary Data
No Article Media
No Metrics

Document Type: Research Article

Publication date: July 15, 2011

  • Access Key
  • Free content
  • Partial Free content
  • New content
  • Open access content
  • Partial Open access content
  • Subscribed content
  • Partial Subscribed content
  • Free trial content
Cookie Policy
Cookie Policy
Ingenta Connect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more