Title
Synthesis and evaluation of cytotoxic and Na+/K+-ATP-ase inhibitory activity of selected 5α-oleandrigenin derivatives
Author
Karol Michalak, Lucie Rárová, Martin Kubala, Petra Čechovác, Miroslav Strnad, Jerzy Wicha
Year
2019
Journal
European Journal of Medicinal Chemistry
Abstract
Oleandrin, the major biologically active constituent of shrub Nerium oleanderpreparations of which have been used in traditional Mediterranean and Asian medicine, attracts a great deal of attention due to its pronounced anticancer activity. The synthesis of oleandrigenin model, 16β-hydroxy-3β-methoxy-5α-card-20(22)-enolide 16-acetate, from androstenolone acetate through 17β-(3-furyl)-intermediates has been developed. Several related 17β-(butenolidyl)- and 17β-(furyl)-androstane derivatives were synthesized and tested for in vitrocytotoxic and Na+/K+-ATP-ase inhibitory activities. Comparison of Na+/K+-ATP-ase inhibitory and cytotoxic activity underlines complex nature of the relationship.
Instrument
J-715
Keywords
Circular dichroism, Organic chemistry, Stereochemistry