rdf:type |
|
lifeskim:mentions |
|
pubmed:issue |
11
|
pubmed:dateCreated |
2006-4-24
|
pubmed:abstractText |
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.
|
pubmed:language |
eng
|
pubmed:journal |
|
pubmed:citationSubset |
IM
|
pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Alkanes,
http://linkedlifedata.com/resource/pubmed/chemical/Alkenes,
http://linkedlifedata.com/resource/pubmed/chemical/Antimalarials,
http://linkedlifedata.com/resource/pubmed/chemical/Cyclohexenes,
http://linkedlifedata.com/resource/pubmed/chemical/Epoxy Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Oxygen,
http://linkedlifedata.com/resource/pubmed/chemical/Peroxides,
http://linkedlifedata.com/resource/pubmed/chemical/Sulfhydryl Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Terpenes,
http://linkedlifedata.com/resource/pubmed/chemical/limonene,
http://linkedlifedata.com/resource/pubmed/chemical/nonane
|
pubmed:status |
MEDLINE
|
pubmed:month |
Jun
|
pubmed:issn |
0960-894X
|
pubmed:author |
|
pubmed:issnType |
Print
|
pubmed:day |
1
|
pubmed:volume |
16
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
2991-5
|
pubmed:dateRevised |
2006-11-15
|
pubmed:meshHeading |
pubmed-meshheading:16527481-Alkanes,
pubmed-meshheading:16527481-Alkenes,
pubmed-meshheading:16527481-Animals,
pubmed-meshheading:16527481-Antimalarials,
pubmed-meshheading:16527481-Cyclization,
pubmed-meshheading:16527481-Cyclohexenes,
pubmed-meshheading:16527481-Epoxy Compounds,
pubmed-meshheading:16527481-Molecular Structure,
pubmed-meshheading:16527481-Oxygen,
pubmed-meshheading:16527481-Peroxides,
pubmed-meshheading:16527481-Plasmodium berghei,
pubmed-meshheading:16527481-Structure-Activity Relationship,
pubmed-meshheading:16527481-Sulfhydryl Compounds,
pubmed-meshheading:16527481-Terpenes
|
pubmed:year |
2006
|
pubmed:articleTitle |
Diels-Alder/thiol-olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophore.
|
pubmed:affiliation |
Department of Chemistry, University of Liverpool, PO Box 147, Liverpool L69 3BX, UK. P.M.oneill01@liv.ac.uk
|
pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
|