7.alpha.-Substituted derivatives of androstenedione as inhibitors of estrogen biosynthesis

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Abstract
In an effort to obtain more information on the structure-activity relationship among the 7.alpha.-(phenylthio)endrostenedione inhibitors of the enzyme aroamatase, 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 the iododerivative, appeared to be quite potent inhibitors. The 125I analog of the iododerivative was synthesized in order to evaluate the possibility of side-chain elimination under the assay conditions. Approximately 90% of [125I]-analog remained intact for up to 1 h under assay conditions. [Agents that control estrogen biosynthesis may be of therapeutic usefulness. Estrogens have been implicated in the development or maintenance of endometrial and mammary carcinoma.].