7 alpha-substituted derivatives of androstenedione as inhibitors of estrogen biosynthesis.
In an effort to obtain more information on the structure-activity relationship among the 7 alpha-(phenylthio)androstenedione inhibitors of the enzyme aromatase, a series of compounds containing both electron-donating and electron-withdrawing ring substituents was synthesized and tested for aromatase inhibitory activity. No linear correlation between substituent electronic effects and inhibitory activity was observed. The halogen-containing compounds, particularly 8, appeared to be quite potent inhibitors. The 125I analogue of 8 was synthesized in order to evaluate the possibility of side-chain elimination under the assay conditions. Approximately 90% of [125I]-8 remained intact for up to 1 h under assay conditions.
D000735:Androstenedione / Q000031:analogs & derivatives*; D047072:Aromatase Inhibitors; D004967:Estrogens / Q000096:biosynthesis*; D005260:Female; D006801:Humans; D010088:Oxidoreductases / Q000037:antagonists & inhibitors*; D010920:Placenta / Q000201:enzymology; D011247:Pregnancy; D013329:Structure-Activity Relationship
D047072:Aromatase Inhibitors; D004967:Estrogens; D000735:Androstenedione; D010088:Oxidoreductases