Antiparasitic agents. 6. Synthesis and anthelmintic activities of novel isothiocyanatophenyl-1,2,4-oxadiazoles

J Med Chem. 1985 Sep;28(9):1234-41. doi: 10.1021/jm00147a019.

Abstract

The syntheses and anthelmintic activities of 31 3- and 5-(isothiocyanatophenyl)-1,2,4-oxadiazoles are reported. In the primary anthelmintic screen, 3-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (39) showed 100% nematocidal activity and 3-(2-furanyl)-5-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (63), 3-(2-furanyl)-5-(2-chloro-4-isothiocyanatophenyl)-1,2,4-oxadiazole (64), and 3-(2-furanyl)-5-(4-chloro-3-isothiocyanatophenyl)-1,2,4-oxadiazole (66) showed 100% taeniacidal activity when administered orally to mice. The two most active members of this series, 39 and 63, were active against the gastrointestinal nematodes of sheep at 100 mg/kg. In addition, 39 was also found to be active against hookworms in dogs at a single, oral dose of 200 mg/kg.

MeSH terms

  • Ancylostomiasis / drug therapy
  • Animals
  • Cat Diseases / drug therapy
  • Cats
  • Chemical Phenomena
  • Chemistry
  • Dog Diseases / drug therapy
  • Dogs
  • Drug Evaluation, Preclinical
  • Haemonchiasis / drug therapy
  • Helminthiasis / drug therapy*
  • Helminthiasis, Animal
  • Hymenolepiasis / drug therapy
  • Mice
  • Nematode Infections / drug therapy
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / therapeutic use*
  • Sheep
  • Sheep Diseases / drug therapy
  • Taeniasis / drug therapy
  • Thiocyanates / chemical synthesis
  • Thiocyanates / therapeutic use*

Substances

  • Oxadiazoles
  • Thiocyanates