Synthesis and biological activity of some new 1,3,4-thiadiazole and 1,2,4-triazole compounds containing a phenylalanine moiety

Molecules. 2009 Jul 16;14(7):2621-31. doi: 10.3390/molecules14072621.

Abstract

New 1,3,4-thiadiazole, 6, 7 and 1,2,4-triazole derivatives, 8, 9 containing a phenylalanine moiety have been synthesized by intramolecular cyclization of 1,4-disubstituted thiosemicarbazides, 4, 5, in acid and alkaline media, respectively; the thiosemicarbazides were obtained by reaction of hydrazide 3 with appropriate aromatic isothiocyanates. The toxicity of the synthesized compounds was evaluated and the anti-inflammatory study of the triazole compound 9 established an appreciable anti-inflammatory activity that is comparable with that of other nonsteroidal anti-inflammatory agents.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Male
  • Mice
  • Phenylalanine / chemistry
  • Rats
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / chemistry
  • Thiadiazoles / pharmacology*
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Thiadiazoles
  • Triazoles
  • 1,3,4-thiadiazole
  • 1,2,4-triazole
  • Phenylalanine