title: Potent antimalarial 1,2,4-trioxanes through perhydrolysis of epoxides.
abstract: Perhydrolysis of a sterically congested multifunctional epoxide was achieved in ethereal H2O2 with the aid of a recently developed Mo catalyst. The resulting hydroperoxide cyclized to give a 1,2,4-trioxane, which could be readily elaborated into qinghaosu and a range of novel analogues. Some of the compounds with two such trioxane moieties showed in vitro antimalarial activity comparable to or even better than that of artesunate or chloroquine.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institution of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, PR China.
authors.forename: Hong-Dong
authors.initials: HD
authors.lastname: Hao
authors.forename: Sergio
authors.initials: S
authors.lastname: Wittlin
authors.forename: Yikang
authors.initials: Y
authors.lastname: Wu
mesh_terms: D000962:Antimalarials / Q000737:chemistry* / Q000494:pharmacology; D037621:Artemisinins / Q000737:chemistry*; D000077332:Artesunate; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000494:pharmacology*; D006861:Hydrogen Peroxide / Q000737:chemistry*
chemical_list: C503429:1,2,4-trioxane; D000962:Antimalarials; D037621:Artemisinins; D004852:Epoxy Compounds; D006571:Heterocyclic Compounds; D000077332:Artesunate; C031327:artemisinin; D006861:Hydrogen Peroxide