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 Chemistry2010Vol. 8(9), pp. 2068–2068
Citations Over TimeTop 16% of 2010 papers
Richard K. Amewu, Peter Gibbons, Amira Mukhtar, Andrew V. Stachulski, Stephen A. Ward, C. Richard Hall, Karen Rimmer, Jill Davies, Livia Vivas, John Bacsa, Amy E. Mercer, Gemma L. Nixon, Paul A. Stocks, Paul M. O’Neill
Abstract
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.
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