Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial activities

Eur J Med Chem. 2010 Nov;45(11):4726-32. doi: 10.1016/j.ejmech.2010.07.018. Epub 2010 Aug 19.

Abstract

Acetohydrazide derivative containing both antipyrine and triazole nuclei (5) was obtained starting from ethyl hydrazinecarboxylate derivative (2) and 4-aminoantipyrine (1) by three steps. The treatment of compound 5 with CS(2) afforded the conversion of hydrazide function into 5-mercapto-1,3,4-oxadiazole ring leading to the formation of 7. Then, 7 gave the product containing triazolotriazine moiety (9) by the reaction with hydrazine hydrate. The synthesis of the compounds incorporating the 1,3,4-thiadiazole (10a-c), 1,2,4-triazole (11a-c) or 1,3-thiazole (12, 13) nucleus as third heterocycle was performed by the acidic or basic treatment of compounds 6a-c which were obtained from the reaction of 5 with several isothiocyanates, or by the condensation of 6a with two different phenacyl bromides, respectively. The antimicrobial activity study revealed that all the compounds showed good activities except 3-5.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Antipyrine / chemistry*
  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Spectrophotometry, Infrared
  • Triazoles / chemistry*

Substances

  • Anti-Infective Agents
  • Triazoles
  • Antipyrine