Synthesis of selectively deuterated and tritiated lupane derivatives

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F13%3A33147739" target="_blank" >RIV/61989592:15310/13:33147739 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15110/13:33147739
Result on the web
<a href="http://dx.doi.org/10.1007/s10967-013-2533-8" target="_blank" >http://dx.doi.org/10.1007/s10967-013-2533-8</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1007/s10967-013-2533-8" target="_blank" >10.1007/s10967-013-2533-8</a>

Result language
angličtina
Original language name
Synthesis of selectively deuterated and tritiated lupane derivatives
Original language description
The aim of this work was to synthesize deuterated and tritiated analogues of highly oxidized lupane derivatives known from our group. We selected compounds that previously showed very high cytotoxic activity on multiple cancer cell lines in order to further investigate the mechanism of their action. From starting material (compounds 1-4), we obtained benzyl platanate (5) and its reaction with deuteromethyltriphenylphosphonium iodide gave deuterated compound 6. Following benzyl deprotection gave free acid 7 and oxidation with SeO2 gave 30-oxo-[29-H-2(2)]lup-20(29)-en-28-oic acid (8), which is one of the most active compounds synthesized in our group to date (IC50 6 mu mol/L on CEM cell line). The alkylation of benzyl 2-hydroxy-3-oxolupa-1,20(29)-dien-28-oate (9) with methyliodide or deuteromethyliodide followed by a series of deprotection and hydrogenation steps gave compounds 10-14, where 2 beta-[31-H-2(3)]methoxy-3-oxolupan-20(29)-en-28-oic acid (13) is especially interesting, it show
Czech name
—
Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
<a href="/en/project/GA305%2F09%2F1216" target="_blank" >GA305/09/1216: Study of mechnism of action and structure optimalization of triterpenoids with anti-tumor activity.</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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