EPR evidence for the involvement of free radicals in the iron-catalysed decomposition of qinghaosu (Artemisinin) and some derivatives; Antimalarial action of some polycyclic endoperoxides

被引:83
作者
Butler, AR
Gilbert, BC [1 ]
Hulme, P
Irvine, LR
Renton, L
Whitwood, AC
机构
[1] Univ York, Dept Chem, York YO1 5DD, N Yorkshire, England
[2] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
关键词
alkoxyl antimalarial; artemisinin; electron paramagnetic resonance; peroxides; peroxygen; qinghaosu; radical-rearrangement; radical-fragmentation; spin-trapping;
D O I
10.3109/10715769809066884
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
EPR experiments confirm that reaction of qinghaosu and some related endoperoxides with Fe2+ in aqueous acetonitrile leads to the production of carbon-centred radicals derived by rapid rearrangement of first-formed cyclic alkoxyl radicals. Signals obtained from qinghaosu itself with spin-traps DMPO and DBNBS are assigned to the adducts (15) and (16), a finding which accounts for the formation of the major products (11) and (14).
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页码:471 / 476
页数:6
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