1227742-53-1Relevant articles and documents
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
Amewu, Richard,Gibbons, Peter,Mukhtar, Amira,Stachulski, Andrew V.,Ward, Stephen A.,Hall, Charlotte,Rimmer, Karen,Davies, Jill,Vivas, Livia,Bacsa, John,Mercer, Amy E.,Nixon, Gemma,Stocks, Paul A.,O'Neill, Paul M.
supporting information; experimental part, p. 2068 - 2077 (2010/07/03)
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.
