374898-86-9Relevant academic research and scientific papers
New Lupane Derived Compounds with Pro-Apoptotic Activity in Cancer Cells: Synthesis and Structure-Activity Relationships
?arek, Jan,Klinot, Ji?í,D?ubák, Petr,Klinotová, Eva,Nosková, Věra,K?e?ek, Václav,Ko?ínková, Gabriela,Thomson, Jean Oliver,Jano?t'áková, Anna,Wang, Shudong,Parsons, Simon,Fischer, Peter M.,Zhelev, Nikolai Z.,Hajdúch, Marián
, p. 5402 - 5415 (2003)
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.
