18-甲基雌二醇-3-甲醚11位的结构改变及与抗生育作用的关系

MODIFICATION AT THE 11 POSITION OF 18-METHYL ESTRADIOL-3-METHYL ETHER AND STUDIES ON STRUCTURE-ANTIFERTILITY RELATIONSHIP

摘要: 为了寻找新的甾体雌激素类抗生育药物,从18-甲基炔诺酮中间体——13-乙基-3-甲氧基-雌甾-1,3,5(10),8-四烯-17-酮(1)始,分别合成了六个11取代的18-甲基雌二醇衍生物:11α-羟基物(5)、11α-甲氧基物(12)、11β-羟基物(14)、11β-甲氧基物(16)、9β-11α-羟基物(19)和9β-11α-甲氧基物(21),其中化合物(12)、(16)、(19)、(21)未见文献报道。其结构和构型系根据光谱分析(UV、IR、NMR、MS)和化学转化确定的。

Abstract: In a search for new estrogenic antifertility drugs, six 11-substituted compounds (11α-hydroxyl (5), 11α-methoxyl (12),11βt-hydroxyl (14), 11β-methoxyl (16), 9β-H-11α-hydroxyl (19) and 9β-H-11α-methoxyl (21)) were synthesized from 13-ethyl-3-methoxy-gena-1,3,5 (10), 8-tetraene-17-one (1). The .synthetic route was shown in diagram. Among these compounds, (12),(16), (19) and (21) have not been cited in the literature. Their structures and configurations were confirmed by spectral analysis and chemical transformation.