Natural cardiac-active principles built upon the 14,16β-dihydroxy-5β,14β-androstane core and bearing a heterocyclic substituent at 17β, in particular, a cardenolide - oleandrin and a bufadienolide - bufotalin, are receiving a great deal of attention as potential anticancer drugs. The densely substituted and sterically shielded ring D is the particular structural feature of these compounds. The first synthesis of oleandrigenin from easily available steroid starting material is reported here. Furthermore, selected 17β-(4-butenolidyl)- and 17β-(3-furyl)-14,16β-dihydroxy-androstane derivatives were en route synthesized and examined for their Na⁺/K⁺-ATP-ase inhibitory properties as well as cytotoxic activities in normal and cancer cell lines. It was found that the furyl-analogue of oleandrigenin/bufatalin (7) and some related 17-(3-furyl)- derivatives (19, 21) show remarkably high Na⁺/K⁺-ATP-ase inhibitory activity as well as significant cytotoxicity in vitro. In addition, oleandrigenin 2 compared to derivatives 21 and 25 induced strong apoptosis in human cervical carcinoma HeLa cells after 24 h of treatment.

建立在14,16β-二羟基-5β，14β-雄甾烷核心上并在17β带有杂环取代基的天然心脏活性原理，尤其是心烯醇内酯-夹竹桃苷和丁二烯内酯-布佛他汀，作为潜在药物受到了广泛关注抗癌药。这些化合物的特殊结构特征是稠密取代且受空间屏蔽的环D。本文报道了从容易获得的类固醇原料中首次合成夹竹桃苷元。此外，途中合成了所选的17β-（4-丁烯丙基）-和17β-（3-呋喃基）-14,16β-二羟基-雄烷衍生物，并检查了其Na ⁺ / K ⁺在正常和癌细胞系中的-ATP酶抑制特性以及细胞毒性活性。据发现，夹竹桃的呋喃基-模拟/ bufatalin（7）和一些相关17-（3-呋喃基） -衍生物（19，21）示出了显着的高NA ⁺ / K ⁺ -ATP-酶抑制活性以及显著体外细胞毒性。另外，与衍生物21和25相比，夹竹桃皂苷元2在治疗24小时后诱导人宫颈癌HeLa细胞中的强凋亡。