5-(Hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3 -acetamide, a reduced nitroheterocyclic derivative with potent schistosomicidal properties.
The synthesis and antischistosome properties of 5-(hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3- acetamide (1) are described. The compound was prepared by reduction of the nitrothiazoline (2) with stannous chloride in methanol, and represents the first example of a reduced nitroheterocyclic compound showing potent schistosomicidal properties. The possible relationship of compounds such as 1 to the as yet unidentified reduced active but toxic entities formed in vivo from nitroheterocyclics like metronidazole is discussed.
D000818:Animals; D008288:Malaria / Q000188:drug therapy; D051379:Mice; D009560:Niridazole / Q000627:therapeutic use; D011223:Praziquantel / Q000627:therapeutic use; D012550:Schistosoma mansoni / Q000187:drug effects; D012556:Schistosomicides / Q000138:chemical synthesis*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000627:therapeutic use
D012556:Schistosomicides; D013844:Thiazoles; D011223:Praziquantel; C046913:5-(hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3-acetamide; D009560:Niridazole