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.

Richard Amewu; Peter Gibbons; Amira Mukhtar; Andrew V Stachulski; Stephen A Ward; Charlotte Hall; Karen Rimmer; Jill Davies; Livia Vivas; John Bacsa; +4 more... Amy E Mercer; Gemma Nixon; Paul A Stocks; Paul M O'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
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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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