Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.1/4260
Título: Diels–alder/thiol–olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophore
Autor: O'Neill, Paul M.
Verissimo, Edite
Ward, Stephen A.
Davies, Jill
Korshin, Edward E.
Araújo, Nuna C.
Pugh, Matthew D.
Cristiano, Maria Lurdes Santos
Stocks, Paul A.
Bachi, Mario D.
Data: 2006
Editora: Elsevier
Citação: 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. Diels–Alder/thiol–olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophore, Bioorganic & Medicinal Chemistry Letters, 16, 11, 2991-2995, 2006.
Resumo: Abstract—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.
Peer review: yes
URI: http://hdl.handle.net/10400.1/4260
DOI: http://dx.doi.org/10.1016/j.bmcl.2006.02.059
ISSN: 0960-894X
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