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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
12
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pubmed:dateCreated |
2002-12-27
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pubmed:abstractText |
The natural cembranolide sarcophine (3) and its lactone ring-opened analogue (10) were oxidized using selenium dioxide under different reaction temperatures to prepare hydroxylated derivatives. Nine new compounds were obtained, six of them targeted hydroxylated derivatives. The determination of regio- and stereochemistry as well as the mechanistic considerations on the selectivity observed in these reactions are discussed on the basis of 2D NMR and molecular modeling. In preliminary in vitro tests on inhibition of EBV-EA activation, compounds 10 and 12-15 have shown higher activity than the known chemopreventive agent sarcophytol A.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
0163-3864
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:volume |
65
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1809-14
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:12502319-4-Butyrolactone,
pubmed-meshheading:12502319-Animals,
pubmed-meshheading:12502319-Anthozoa,
pubmed-meshheading:12502319-Anticarcinogenic Agents,
pubmed-meshheading:12502319-Antigens, Viral,
pubmed-meshheading:12502319-Chemoprevention,
pubmed-meshheading:12502319-Dose-Response Relationship, Drug,
pubmed-meshheading:12502319-Egypt,
pubmed-meshheading:12502319-Hydroxylation,
pubmed-meshheading:12502319-Indian Ocean,
pubmed-meshheading:12502319-Models, Molecular,
pubmed-meshheading:12502319-Molecular Structure,
pubmed-meshheading:12502319-Nuclear Magnetic Resonance, Biomolecular,
pubmed-meshheading:12502319-Oxidation-Reduction,
pubmed-meshheading:12502319-Selenium Compounds,
pubmed-meshheading:12502319-Stereoisomerism,
pubmed-meshheading:12502319-Structure-Activity Relationship
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pubmed:year |
2002
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pubmed:articleTitle |
Semisynthesis of new sarcophine derivatives with chemopreventive activity.
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|
pubmed:affiliation |
Department of Pharmacognosy and National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677-1848, USA.
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pubmed:publicationType |
Journal Article,
Comparative Study,
Research Support, U.S. Gov't, Non-P.H.S.,
Research Support, Non-U.S. Gov't
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