d‐Secoestrone derivatives. V

The two title 16,17‐secoestrone derivatives, 3‐methoxy‐17‐oxo‐17‐phenyl‐16,17‐secoestra‐1,3,5(10)‐triene‐16‐nitrile, C₂₅H₂₇NO₂, (I) (17‐oxo substituent), and 17‐hydroxy‐3‐methoxy‐17‐phenyl‐16,17‐secoestra‐1,3,5(10)‐triene‐16‐nitrile, C₂₅H₂₉NO₂, (II) (17‐hydroxy substituent), have quite different conformations in the solid state. These conformational differences can be minimized by molecular mechanics calculations. Thus, the remarkable difference in the biological activity of the two compounds, e.g. the strong oestrogenic characteristics of (I) and the moderate antioestrogenic action of (II), must be caused by the difference in substitution at C17. In (II), the mol­ecules are linked by O—H?N hydrogen bonds, forming spirals along the b direction.