Collect. Czech. Chem. Commun. 2002, 67, 336-352

Cardenamides from Cardenolides: Cardiac and Anticancer Activities

Rudolf Meggesa,b,*, Jürgen Weilanda, Rudolf Schöna, Heinrich Repkeb and Kurt R. H. Repke

a Max Delbrück Center for Molecular Medicine (MDC), D-13092 Berlin-Buch, Germany
b German-American Institute for Applied Biomedical Research GmbH (GAIFAR), D-14 473 Potsdam, Germany


Two ways are shown to transform cardioactive cardenolides into cardenamides [17β-(5-oxo-2,5-dihydropyrrol-3-yl)-5β,14β-androstane derivatives], and their derivatives by replacement of their ring oxygen by N-R. Cardioactivity is strongly decreased by this transformation. The comparatively easily accessible 21-oxocardenamides [17β-(2-maleimidyl)steroids] are strongly thiol reactive and show remarkable anticancer activity.

Keywords: Na+/K+-ATPase inhibition; Cardenolides; Cardenamides; Steroids; Lactams; 21-Oxocardenamides; Anticancer activity.

References: 28 live references.