Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 5402–5415 |
| Number of pages | 14 |
| Journal | Journal of Medicinal Chemistry |
| Volume | 46 |
| Issue number | 25 |
| DOIs | |
| State | Published - 2003 |
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New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure−activity relationships. / 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; Hajdúch, Marián.
In: Journal of Medicinal Chemistry, Vol. 46, No. 25, 2003, p. 5402–5415.Research output: Contribution to journal › Article
TY - JOUR
T1 - New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure−activity relationships
AU - Šarek,Jan
AU - Klinot,Jiří
AU - Džubák,Petr
AU - Klinotová,Eva
AU - Nosková,Věra
AU - Křeček,Václav
AU - Kořínková,Gabriela
AU - Thomson,Jean Oliver
AU - Janošťáková,Anna
AU - Wang,Shudong
AU - Parsons,Simon
AU - Fischer,Peter M.
AU - Zhelev,Nikolai
AU - Hajdúch,Marián
PY - 2003
Y1 - 2003
N2 - 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.
AB - 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.
U2 - 10.1021/jm020854p
DO - 10.1021/jm020854p
M3 - Article
VL - 46
SP - 5402
EP - 5415
JO - Journal of Medicinal Chemistry
T2 - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
SN - 0022-2623
IS - 25
ER -