Source:http://linkedlifedata.com/resource/pubmed/id/14640549
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
25
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pubmed:dateCreated |
2003-12-3
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pubmed:abstractText |
Cellular screening of various synthetic triterpenoid compounds formally derived from lupane has identified a number of analogues as potential anticancer drug candidates. Here we describe the synthesis and structure-activity relationships of betulin and betulinic acid derivatives containing an E-ring modified with different oxygen functions. Thus compounds containing the lup-18-en-21-one, lup-18-ene-21,22-dione, 18,19-secolupane, and the highly oxygenated 18,19-secolupane systems, as well as des-E-lupane derivatives, were prepared from the readily available natural pentacyclic triterpene betulin using oxidative procedures. These compounds were named betulinines. We demonstrate that only selected compounds, particularly those containing a lupane E-ring-derived unsaturated ketone or diketone function, possessed in vitro cytotoxic activity against tumor cell lines, suggesting a structure-activity relationship.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
0022-2623
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pubmed:author |
pubmed-author:DzubákPetrP,
pubmed-author:FischerPeter MPM,
pubmed-author:HajdúchMariánM,
pubmed-author:Janost'ákováAnnaA,
pubmed-author:KlinotJiríJ,
pubmed-author:KlinotováEvaE,
pubmed-author:KorínkováGabrielaG,
pubmed-author:KrecekVáclavV,
pubmed-author:NoskováVeraV,
pubmed-author:ParsonsSimonS,
pubmed-author:SarekJanJ,
pubmed-author:ThomsonJean OliverJO,
pubmed-author:WangShudongS,
pubmed-author:ZhelevNikolai ZNZ
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pubmed:issnType |
Print
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pubmed:day |
4
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pubmed:volume |
46
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
5402-15
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:14640549-Animals,
pubmed-meshheading:14640549-Antineoplastic Agents,
pubmed-meshheading:14640549-Apoptosis,
pubmed-meshheading:14640549-Cell Line, Tumor,
pubmed-meshheading:14640549-Crystallography, X-Ray,
pubmed-meshheading:14640549-Drug Resistance, Neoplasm,
pubmed-meshheading:14640549-Drug Screening Assays, Antitumor,
pubmed-meshheading:14640549-Humans,
pubmed-meshheading:14640549-Mice,
pubmed-meshheading:14640549-Stereoisomerism,
pubmed-meshheading:14640549-Structure-Activity Relationship,
pubmed-meshheading:14640549-Triterpenes
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pubmed:year |
2003
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pubmed:articleTitle |
New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure-activity relationships.
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pubmed:affiliation |
Department of Organic and Nuclear Chemistry, Charles University in Prague, Hlavova 8, 128 43 Prague 2, Czech Republic.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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