Institute of Organic Chemistry, Polish Academy of Sciences, ul. Marcina Kasprzaka 44/52, 01-224, Warsaw, Poland.
Laboratory of Growth Regulators, Institute of Experimental Botany ASCR & Palacky University, Šlechtitelů 27, 783 71, Olomouc, Czech Republic.
Eur J Med Chem. 2019 Oct 15;180:417-429. doi: 10.1016/j.ejmech.2019.07.028. Epub 2019 Jul 9.
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.
由于其显著的抗癌活性，夹竹桃苷，灌木夹竹桃制剂中的主要生物活性成分，引起了人们的极大关注。通过 17β-（呋喃基）中间体，从雄甾酮乙酸酯合成了夹竹桃苷元模型，16β-羟基-3β-甲氧基-5α-card-20（22）-烯醇内酯 16-乙酸酯。合成了几种相关的 17β-（丁烯内酯基）和 17β-（呋喃基）雄烷衍生物，并测试了它们的体外细胞毒性和 Na/K-ATP-ase 抑制活性。Na/K-ATP-ase 抑制活性和细胞毒性活性的比较突出了这种关系的复杂性。
