Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F14%3A33152497" target="_blank" >RIV/61989592:15310/14:33152497 - isvavai.cz</a>
Alternative codes found
RIV/61389030:_____/14:00429932
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S0040402014003123" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402014003123</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2014.03.006" target="_blank" >10.1016/j.tet.2014.03.006</a>

Result language
angličtina
Original language name
Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain
Original language description
A concise synthesis of lupane triterpenes with an elongated carbon chain at the C-28 position, as well as saponins containing D-mannose, L-arabinose, and L-rhamnose moieties at the C-3 position is described. The overall synthesis of the new triterpenes involved seven linear steps starting from natural betulin: selective protection of a hydroxyl group, oxidation, elongation of the carbon chain by Grignard reaction, and deoxygenation. O-Glycosides were obtained by glycosylation of triterpenes with classical Schmidt's donors. Additionally, all new compounds were evaluated in vitro for their cytotoxic activities. Several triterpenes and the corresponding saponins exhibited an interesting cytotoxic activity profile against human cancer cell lines. The therapeutical index of active triterpenes is very high, since almost none of them were cytotoxic for normal BJ fibroblasts. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compoun
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
ED - Physiology
OECD FORD branch
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Project
<a href="/en/project/LO1204" target="_blank" >LO1204: Sustainable development of research in the Centre of the Region Haná</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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