The œstrogenic activity of some condensed-ring compounds in relation to their other biological activities

Abstract

The very rapid progress which has been made recently in the chemistry of the œstrogenic hormones, of which an excellent has been given by Girard (1933) has established that these substances are hydrogenated phenanthrene derivatives containing oxygen in the molecule ( cf . Butenandt, Weidlich, and Thompson, 1933). On the assumption of a biological relationship between these hormones and the sterols and bile acids, an assumption which seems justifiable, although it cannot yet be regarded as rigidly proved, œstrone (= ketohydroxyœstratriene) is probably represented by formula I or II. The present communication describes the examination for œstrogenic properties of a number of condensed carbon-ring compounds of somewhat analogous structure in an attempt to elucidate the molecular conditions necessary for œstrogenic activity. A preliminary account of some of these experiments has already been given (cook, Dodds, and Hewett, 1933; cook and Dodds, 1933). Our investigations have brought to light a number of pure synthetic compounds, of known molecular structure, which show this physiological activity, and in some of the compounds studied the activity is of a very high order. It will be observed that one of two oxygen atoms in œstrone is ketonic and the other hydroxylic. Girard (1933) has suggested that these two types of oxygen-containing groups are biologically equivalent, and our own experiments group but no hydroxyl group, whereas others contain only hydroxyl groups in a similar type of molecule.