Chemotherapeutic agents, XV. Synthesis of 4-amino-3-pyrazolo-1,2,4-triazoles as antimicrobial agents

Arch Pharm (Weinheim). 1989 Feb;322(2):63-6. doi: 10.1002/ardp.19893220202.

Abstract

4-Amino-3-hydrazino-5-H/methyl-1,2,4-triazole dihydrochlorides (2a,b) were obtained by cyclization of triamino-guanidine-HCl in formic and acetic acids, respectively. Condensation of 2a with pyrazol-4-carbaldehydes in ethanol yielded 3a,b. Cyclocondensation of 2a,b with dimethylmercaptocyanoacrylonitrile, methyl dimethylmercapto-cyanoacrylate, ethoxymethylenemalononitrile and ethyl ethoxymethylenecyanoacetate individually provided 4a-d and 5a-d, respectively. The hydrazones 6a,b were obtained by refluxing 4-amino-3-(5-amino-4-ethoxycarbonyl pyrazol-1-yl)-1,2,4-triazole (5b) with aryl aldehydes in ethanol. Interaction of 2a with acetylacetone and 2-ethoxycarbonylcyclopentanone separately yielded 7 and 8 while reaction with 2-ethoxycarbonylcyclohexanone provided the bicyclic compounds 9a,b. Some of the compounds were screened for antibacterial and antifungal activities but none of them showed any significant activity.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Microbial Sensitivity Tests
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology

Substances

  • Anti-Infective Agents
  • Pyrazoles
  • Triazoles