Synthetic Estrogenic Compounds. I. Monosubstituted Derivatives of 1,3-Di-(p-hydroxyphenyl)-propane

Abstract

Derivatives of 1,3-Di-(^-hydroxyphenyl) -propane 1579 4-hydroxyphenyl)-ethane, in common with hexestrol, are geometrically related to estradiol but, in contrast, have no estrogenic activity.2. The amino analog of hexestrol, 3,4-bis-(£aminophenyl)-hexane, is inactive.3. Replacement of the ^-hydroxyphenyl groups of hexestrol with 3,4-dihydroxyphenyl or p-hydroxybenzyl results in decreased estrogenic activity.Pearl River, N. Y.

Artificial Estrogens

“…The earlier work of Blanchard, Stuart, and Tallman (25,474) on the diphenylpropane estrogens led to the discovery of the active compound 2,4-bis(p-hydroxyphenyl)-3-ethylhexane (CXCV), known as benzestrol. The estrogenic acp-HOC6H4CH-CH-CHCeBOH-p…”

Synthetic Estrogens and the Relation Between their Structure and their Activity.

“…Baker (6) endeavored to obtain substances still conforming to the estradiol pattern but with its hydronaphthalene skeleton ruptured at places other than in hexestrol. Among these compounds, written according to Baker, (12,206,207) at first followed similar lines and synthesized l-(m-hydroxyphenyl)-3-(p-hydroxyphenyl)hexane (CXLII), which is moderately active. These authors then disregarded the hypothetical structural resemblance and prepared a series of di(p-hydroxyphenyl)propane derivatives and concluded, on the basis of their results, that this resemblance is coincidental.…”