Syntheses and anthelmintic activity of alkyl 5(6)-(substituted-carbamoyl)- and 5(6)-(disubstituted-carbamoyl)benzimidazole-2-carbamates and related compounds.
A number of alkyl 5(6)-(substituted-carbamoyl)- and 5(6)-(disubstituted-carbamoyl)benzimidazole-2-carbamates and related compounds have been synthesized, and their anthelmintic activity against various intestinal helminths of experimental animals have been evaluated. A large percentage of the compounds synthesized showed noteworthy activity against Ancylostoma ceylanicum and at higher doses against Hymenolepsis nana infections. Compared to the alkyl 5(6)-(substituted-carbamoyl)benzimidazole-2-carbamates, the disubstituted carbamoyl analogues were found to exhibit better anthelmintic activity. The most active compound of the series, namely, methyl 5(6)-[(N-2-pyridylpiperazino)carbamoyl]benzimidazole-2-carbamate (90), has been screened against intestinal helminths in higher animals and as a micro- and macrofilaricidal agent. Compound 90 has been identified as a broad-spectrum anthelmintic agent. Compound 90 has been identified as a broad-spectrum anthelmintic in view of its efficacy against A. ceylanicum (hamsters and dogs), H. nana (rats), Nippostrongylus brasiliensis (rats), Syphacia obvelata (mice), A. tubaeformis (cat), Toxocara spp. (cat), and Litomosoides carinii (cotton rat).
D000724:Ancylostomiasis / Q000188:drug therapy; D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis*; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000627:therapeutic use; D002219:Carbamates / Q000138:chemical synthesis* / Q000627:therapeutic use; D002415:Cats; D002590:Cestode Infections / Q000188:drug therapy; D006224:Cricetinae; D004285:Dogs; D005260:Female; D005368:Filariasis / Q000188:drug therapy; D006725:Hookworm Infections / Q000188:drug therapy; D008297:Male; D051379:Mice; D009559:Nippostrongylus; D010123:Oxyuriasis / Q000188:drug therapy; D010124:Oxyuroidea; D051381:Rats; D013329:Structure-Activity Relationship
D000871:Anthelmintics; D001562:Benzimidazoles; D002219:Carbamates