title: Antiparasitic agents. 6. Synthesis and anthelmintic activities of novel isothiocyanatophenyl-1,2,4-oxadiazoles.
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: D000724:Ancylostomiasis / Q000188:drug therapy; D000818:Animals; D002371:Cat Diseases / Q000188:drug therapy; D002415:Cats; D055598:Chemical Phenomena; D002621:Chemistry; D004283:Dog Diseases / Q000188:drug therapy; D004285:Dogs; D004353:Drug Evaluation, Preclinical; D006188:Haemonchiasis / Q000188:drug therapy; D006373:Helminthiasis / Q000188:drug therapy*; D006374:Helminthiasis, Animal; D006925:Hymenolepiasis / Q000188:drug therapy; D051379:Mice; D009349:Nematode Infections / Q000188:drug therapy; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000627:therapeutic use*; D012756:Sheep; D012757:Sheep Diseases / Q000188:drug therapy; D013622:Taeniasis / Q000188:drug therapy; D013861:Thiocyanates / Q000138:chemical synthesis / Q000627:therapeutic use*
chemical_list: D010069:Oxadiazoles; D013861:Thiocyanates