Synthesis and molluscicidal activity of some new thiophene, thiadiazole and pyrazole derivatives

Eur J Med Chem. 2009 Mar;44(3):1250-6. doi: 10.1016/j.ejmech.2008.09.006. Epub 2008 Sep 16.

Abstract

The base-catalyzed reaction of benzoyl acetone 1 with phenyl isothiocyanate yields the non-isolable intermediate 2. Treatment of 2 with dilute HCl afforded the corresponding thiocarbamoyl derivative 3. Reaction of the intermediate 2 with phenacyl bromide, ethyl bromoacetate, chloroacetonitrile, chloroacetyl chloride, bromodiethyl malonate and chloroacetone afforded the corresponding thiophene derivatives 5, 8, 15 and 17. The thiocarbamoyl derivative 3 reacts with arylazophenacyl bromide and/or hydrazine hydrate to afford the corresponding thiadiazole and pyrazole derivatives 20a-c and 22, respectively. These new synthesized compounds show generally a moderate molluscicidal activity to Biomphalaria alexandrina snails.

MeSH terms

  • Animals
  • Biomphalaria / drug effects*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Spectrum Analysis / methods
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / chemistry
  • Thiadiazoles / pharmacology
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry
  • Thiophenes / pharmacology

Substances

  • Pyrazoles
  • Thiadiazoles
  • Thiophenes