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

摘要

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, 16 beta-hydroxy-3 beta-methoxy-5 alpha-card-20(22)-enolide 16-acetate, from androstenolone acetate through 17 beta-(3-furyl)-intermediates has been developed. Several related 17 beta-(butenolidyl)- and 17 beta-(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. (C) 2019 Elsevier Masson SAS. All rights reserved.