Premium
Potent Antimalarial 1,2,4‐Trioxanes through Perhydrolysis of Epoxides
Author(s) -
Hao HongDong,
Wittlin Sergio,
Wu Yikang
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300076
Subject(s) - trioxane , artesunate , epoxide , steric effects , chemistry , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , plasmodium falciparum , malaria , copolymer , medicine , immunology , polymer
Abstract Perhydrolysis of a sterically congested multifunctional epoxide was achieved in ethereal H 2 O 2 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.