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Please use this identifier to cite or link to this item: http://hdl.handle.net/10373/252

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Title: New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure−activity relationships
Authors: Šarek, Jan
Klinot, Jiří
Džubák, Petr
Klinotová, Eva
Nosková, Věra
Křeček, Václav
Kořínková, Gabriela
Thomson, Jean Oliver
Janošťáková, Anna
Wang, Shudong
Parsons, Simon
Fischer, Peter M.
Zhelev, Nikolai Z.
Hajdúch, Marián
Affiliation: University of Abertay Dundee. School of Social and Health Sciences
Keywords: Cancer cells
Issue Date: 2003
Publisher: American Chemical Society
Type: Journal Article
Refereed: peer-reviewed
Rights: Published version © American Chemical Society, available from www.pubs.acs.org
Citation: Šarek, J. 2003. New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure−activity relationships. Journal of Medicinal Chemistry. 46(25): pp.5402–5415. [Online] Available from: DOI: http://dx.doi.org/10.1021/jm020854p
Abstract: 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.
URI: http://hdl.handle.net/10373/252
ISSN: 0022-2623
Appears in Collections:Social & Health Sciences Collection

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