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化学学报
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化学学报 ›› 1980, Vol. 38 ›› Issue (5): 489-491. 上一篇    下一篇

研究简报

炔雌醚-6-酮-(O-羧甲基)肟和炔雌醇-6-酮-(O-羧甲基)肟的合成

邴圣民1, 陆锦山2   

  1. 1. 上海第一医学院妇产科研究所;
    2. 上海第九制药厂中心试验室
  • 投稿日期:1978-08-29 发布日期:2013-06-03

SYNTHESIS OF 6-OXO-QUINESTROL-6-(O-CARBOXYMETHYL) OXIME AND 6-OXO-ETHYNYLESTRADIOL-6-(O-CARBOXYMETHYL) OXIME

BING SHENG-MIN1, LU JIN-SHAN2   

  1. 1. Research Institute of Obstetrics and Gynecology, Shanghai First Medical College;
    2. Central Laboratory, Shanghai No.9 Pharmaceutical Works
  • Received:1978-08-29 Published:2013-06-03

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为了研究长效口服避孕药复方炔雌醚的作用机理,我们采用放射免疫测定法,测定服药者血中炔雌醚(17α-乙炔雌二醇-3-环戊醚)及其代谢产物炔雌醇(17α-乙炔雌二醇)的浓度,以观察它们的动态变化规律.甾体化合物的分子量较小,本身没有抗原性,所以须先制备半抗原,然后再与大分子载体,如牛血清白蛋白结合,方能使动物免疫而产生抗血清.目前甾体雌激素的半抗原多采用6-(O-羧甲基)肟衍生物.通常先用铬酐-乙酸氧化雌激素,引入6-酮基,再制成肟衍生物.但是铬酐-乙酸的氧化产物甚为复杂,得率亦低.

A synthesis of the haptens of the long acting oral contraceptive quinestrol and its metabolic product ethynylestradiol has been described.Norlutin was used as the Starting material and oxidized according to the method of yeild the ld the 6-oso-ethynylestradiol,which was than reached with cyclopentyl bromide to give-the 6-oxo-ethynylestradiol.Both 6-oxo-ethynylestradiol and 6-oxo-quinestrol were then reacted respectively with carhoxy-methoxylamine hemihydro-chloride to give the corresponding 6-(O-carboxymethyl) oxime derivatives of 6-oxo-quinestrol and 6-oxo-ethynylestradiol.