Antimalarial activity of yingzhaosu A analogues.
Iodonium ion mediated cyclization of unsaturated hydroperoxides 1 afforded the expected yingzhaosu A analogues 2. In some cases, however, the corresponding cyclic ethers 5 were formed competitively with the cyclic peroxides 2, the ratios of these two products being a marked function of the structure of the starting materials. Some of the cyclic peroxides 2 showed significant antimalarial activities in vitro and in vivo.
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D002384:Catalysis; D002460:Cell Line; D003500:Cyclization; D008288:Malaria / Q000188:drug therapy; D051379:Mice; D008813:Mice, Inbred ICR; D009861:Onium Compounds; D010545:Peroxides; D010962:Plasmodium berghei; D010963:Plasmodium falciparum / Q000187:drug effects; D011725:Pyridines; D012717:Sesquiterpenes; D013329:Structure-Activity Relationship
D000962:Antimalarials; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009861:Onium Compounds; D010545:Peroxides; D011725:Pyridines; D012717:Sesquiterpenes; C080714:iodonium dicollidine; C467230:yingzhaosu A