Crabbé P, Fillion H, Letourneaux Y, Diczfalusy E, Aedo A R, Goldzieher J W, Shaikh A A, Castracane D
Steroids. 1979 Jan;33(1):85-96. doi: 10.1016/s0039-128x(79)80008-2.
The chemical synthesis of 2 alpha, 17 alpha-diethynyl-A-nor-5 alpha-androstane-2 beta, 17 beta-diol dipropionate (Anordrin) and the corresponding diacetate is reported. Similarly, the preparation of the 2 alpha, 17 alpha-diethynyl-A-nor-5 alpha-estrane-2 beta, 17 beta-diol, its diacetate and dipropionate (Dinordrin I), along with the corresponding 2 beta-epimer (Dinordrin II) from 17 beta-hydroxy-A-nor-5 alpha=estran-2-one is described. In rat uterotrophic activity bioassay, the slope of ethynylestradiol differed significantly from the slopes of the other three compounds, thus vitiating potency estimates with this reference compound. Dinordrin I was 20 times more potent than Anordrin and considerably more potent then Dinordrin II. The single-dose oral antifertility effect in rats generally paralleled uterotrophic activity. Immediate postovulatory contraceptive effectiveness was assessed in adult cycling female baboons given two doses daily for 4 days. Both Anordrin and Dinordrin I showed antifertility activity worthy of further study. Moreover, a definite luteolytic effect, with depression of both plasma estrogen and progesterone levels, was observed with these two steroids.
报道了2α,17α - 二乙炔基 - A - 降 - 5α - 雄甾烷 - 2β,17β - 二醇二丙酸酯（双炔失碳酯）及相应二乙酸酯的化学合成。同样，描述了由17β - 羟基 - A - 降 - 5α - 雌甾 - 2 - 酮制备2α,17α - 二乙炔基 - A - 降 - 5α - 雌甾烷 - 2β,17β - 二醇及其二乙酸酯和二丙酸酯（炔诺酮Ⅰ），以及相应的2β - 差向异构体（炔诺酮Ⅱ）的方法。在大鼠子宫增重活性生物测定中，乙炔雌二醇的斜率与其他三种化合物的斜率有显著差异，因此用该对照化合物进行效价估计是无效的。炔诺酮Ⅰ的效力比双炔失碳酯强20倍，且比炔诺酮Ⅱ强得多。大鼠单剂量口服抗生育作用一般与子宫增重活性平行。对成年发情周期的雌性狒狒每天给药两次，连续给药4天，评估排卵后立即避孕的有效性。双炔失碳酯和炔诺酮Ⅰ均显示出值得进一步研究的抗生育活性。此外，观察到这两种甾体具有明确的溶黄体作用，同时伴有血浆雌激素和孕酮水平的降低。
