Synthesis and evaluation of cytotoxic and Na+/K+-ATP-ase inhibitory activity of selected 5 alpha-oleandrigenin derivatives

0509603 - ÚEB 2020 RIV FR eng J - Článek v odborném periodiku
Michalak, K. - Rárová, Lucie - Kubala, M. - Čechová, P. - Strnad, Miroslav - Wicha, J.
Synthesis and evaluation of cytotoxic and Na+/K+-ATP-ase inhibitory activity of selected 5 alpha-oleandrigenin derivatives.
European Journal of Medicinal Chemistry. Roč. 180, OCT 15 (2019), s. 417-429. ISSN 0223-5234. E-ISSN 1768-3254
Grant CEP: GA ČR GA17-14007S; GA ČR(CZ) GA19-01383S
Institucionální podpora: RVO:61389030
Klíčová slova: ATP-ase inhibition * Cardenolides * Cytotoxicity * Furan transformation * Partial synthesis
Obor OECD: Organic chemistry
Impakt faktor: 5.573, rok: 2019
Způsob publikování: Open access
http://dx.doi.org/10.1016/j.ejmech.2019.07.028

Oleandrin, the major biologically active constituent of shrub Nerium oleander preparations 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 vitro cytotoxic and Na+/K+-ATP-ase inhibitory activities. Comparison of Na+/K+-ATP-ase inhibitory and cytotoxic activity underlines complex nature of the relationship.
Trvalý link: http://hdl.handle.net/11104/0300295