Synthesis of 2,5-disubstituted benzimidazoles, 1,3,4-thiadiazoles and 3,5-diiodosalicylanilides as structural congeners of rafoxanide and closantel.
The synthesis of a series of 2,5-disubstituted benzimidazoles (8-10, 13), substituted 3,5-diodosalicylanilides (6, 7, 11, 12, 16-29), 2-(4-substituted phenyl)-4-aroylamino-1,3,4-thiadiazoles (33-38) and benzoxazines (14, 30, 31) has been carried out as the structural congeners of rafoxanide and closantel. All the compounds have been tested for their anthelmintic activity against Ancylostoma ceylanicum, Nippostrongylus brasiliensis, Hymenolepis nana and Cysticecus fasciolaris in rodents. Compounds 8, 22 and 23 exhibited 90-100% elimination of the hookworms A. ceylanicum and tapeworms H. nana from hamsters and rats, respectively, at an oral dose 50-250 mg/kg body mass.
Srivastava
R P
RP
Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India.
Sharma
S
S
D000722:Ancylostoma / Q000187:drug effects; D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis*; D001562:Benzimidazoles / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003552:Cysticercus / Q000187:drug effects; D006926:Hymenolepis / Q000187:drug effects; D009559:Nippostrongylus / Q000187:drug effects; D011888:Rafoxanide / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D012457:Salicylamides / Q000138:chemical synthesis*; D012458:Salicylanilides / Q000138:chemical synthesis* / Q000494:pharmacology; D013830:Thiadiazoles / Q000138:chemical synthesis*
D000871:Anthelmintics; D001562:Benzimidazoles; D012457:Salicylamides; D012458:Salicylanilides; D013830:Thiadiazoles; D011888:Rafoxanide; C023342:closantel