Solo A J, Bejba N, Hebborn P, May M
J Med Chem. 1975 Feb;18(2):165-8. doi: 10.1021/jm00236a011.
The benzyl (2), allyl (4), propyl (10), 3-hydroxypropyl (12), 2,3-dihydroxypropyl (11), 4 pentenyl (7), and pentyl (8) ethers of testosterone were synthesized. Compounds 2, 4, 7, 8, 10, and 12 were found to be almost devoid of anabolic or androgenic activity in a modified Hershberger Assay, but 2,4,10, and 12 were found to be effective inhibitors of testosterone 5alpha-reductase from human skin. These findings suggest that esters of testosterone and of 19-nortestosterone must hydrolyze before interacting with the hormonal receptors, but that the esters may competitively compete with the parent alchohols for interaction with enzymes. The latter effect may shift the distribution of metabolites of the esters relative to the alchohols and thus influence the pharmacological effect of these compounds.
合成了睾酮的苄基醚（2）、烯丙基醚（4）、丙基醚（10）、3-羟丙基醚（12）、2,3-二羟丙基醚（11）、4-戊烯基醚（7）和戊基醚（8）。在改良的赫希伯格试验中，发现化合物2、4、7、8、10和12几乎没有合成代谢或雄激素活性，但发现2、4、10和12是人体皮肤睾酮5α-还原酶的有效抑制剂。这些发现表明，睾酮和19-去甲睾酮的酯在与激素受体相互作用之前必须水解，但酯可能会与母体醇竞争与酶的相互作用。后一种效应可能会改变酯相对于醇的代谢产物分布，从而影响这些化合物的药理作用。
