Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols.
RichardAmewu;
PeterGibbons;
AmiraMukhtar;
Andrew VStachulski;
Stephen AWard;
CharlotteHall;
KarenRimmer;
JillDavies;
LiviaVivas;
JohnBacsa;
+4 more...
Amy EMercer;
GemmaNixon;
Paul AStocks;
Paul MO'Neill;
(2010)
Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols.
Organic & biomolecular chemistry, 8 (9).
pp. 2068-2077.
ISSN 1477-0520
DOI: 10.1039/b924319d
Thiol-Olefin Co-Oxygenation (TOCO) methodology has been applied to the synthesis of a small library of weak base and polar 1,2,4-trioxanes. The 1,2,4-trioxane units synthesised exhibit remarkable stability as they survive base catalysed hydrolysis and mixed anhydride/amine coupling reactions. This unique stability feature has enabled a range of novel substitution patterns to be incorporated within the spiro 1,2,4-trioxane unit. Selected analogues express potent in vitro nM antimalarial activity, low cytotoxicity and oral activity in the Plasmodium berghei mouse model of malaria.
Item Type | Article |
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Keywords | highly stereoselective-synthesis, antiproliferative activity, bicyclic, peroxides, artemisinin, derivatives, drug, methodology, malaria, design, potent |
ISI | 276786000013 |
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