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|Title: ||New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure−activity relationships|
|Authors: ||Šarek, Jan|
Thomson, Jean Oliver
Fischer, Peter M.
Zhelev, Nikolai Z.
|Affiliation: ||University of Abertay Dundee. School of Social and Health Sciences|
|Keywords: ||Cancer cells|
|Issue Date: ||2003|
|Publisher: ||American Chemical Society|
|Type: ||Journal Article|
|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.|
|Appears in Collections:||Social & Health Sciences Collection|
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