833-38-5Relevant articles and documents
Diels-Alder/thiol-olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophore
O'Neill, Paul M.,Verissimo, Edite,Ward, Stephen A.,Davies, Jill,Korshin, Edward E.,Araujo, Nuna,Pugh, Matthew D.,Cristiano, M. Lurdes S.,Stocks, Paul A.,Bachi, Mario D.
, p. 2991 - 2995 (2008/09/20)
A Diels-Alder/thiol-olefin co-oxygenation approach to the synthesis of novel bicyclic endoperoxides 17a-22b is reported. Some of these endoperoxides (e.g., 17b, 19b, 22a and 22b) have potent nanomolar in vitro antimalarial activity equivalent to that of the synthetic antimalarial agent arteflene. Iron(II)-mediated degradation of sulfone-endoperoxide 19b and spin-trapping with TEMPO provide a spin-trapped adduct 25 indicative of the formation of a secondary carbon centered radical species 24. Reactive C-radical intermediates of this type may be involved in the expression of the antimalarial effect of these bicyclic endoperoxides.