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Chemical synthesis and bioassay of anordrin i anordrin ii dinordrin i and dinordrin ii



Chemical synthesis and bioassay of anordrin i anordrin ii dinordrin i and dinordrin ii



Steroids 33(1): 85-96



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 3 compounds, thus vitiating potency estimates with this reference compound. Dinordrin I was 20 times more potent than Anordrin and considerably more potent than 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 2 doses daily for 4 days. Both Anordrin and Dinordrin I showed antifertility activity worthy of further study. A definite luteolytic effect, with depression of both plasma estrogen and progesterone levels, was observed with these 2 steroids.

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Accession: 004939614

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