139255-68-8Relevant articles and documents
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 (2007/10/03)
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.
FUNCTIONALIZATION OF 3β,28-LUPANEDIOL DIACETATE WITH CHROMIUM(VI) OXIDE
Sejbal, Jan,Klinot, Jiri,Budesinsky, Milos,Protiva, Jiri
, p. 2936 - 2949 (2007/10/02)
The oxidation of 3β,28-lupanediol diacetate (I) with chromium (VI) oxide gives low yields of products with functional groups in the ring E as products of hydroxylation at the 19β position (IV, VI, and IX) and the 11-ketone VII which has been transformed into other lupane derivatives with an oxygen functional group at 11 position (VIII, XIII - XV) or with a 9(11)-double bond (XVI, XVII).Structure of the compounds prepared has been verified by their 1H and 13C NMR spectra as well as by their mass spectra.
