Studies on Steroidal Ethers: Uterotrophic, Oviductotrophic and Lipid-Shifting Properties of Some 3-Ethers of Estrone1

Abstract

Several 3-ethers of estrone were assayed both orally and parenterally for the following activities: 1) ability tb induce uterine growth in immature mice; 2) ability to increase the serum phospholipid level and to decrease the cholesterol-phospholipid ratio in chicks fed a cholesterol-enriched diet; 3) ability to induce oviduct growth in chicks. The uterotrophic activity of the assayed ethers was very low following parenteral administration, whereas, by mouth, n-butyl, n-amyl, isoamyl and cyclopentyl derivatives were found to be more potent than estrone itself. As to the lipid-shifting properties displayed in chicks by estrone ethers, those carrying straight chain alcohols with an odd number of carbon atoms were in general much more potent, both orally and parenterally, than those derived from even-numbered carbon chain alcohols. Particular emphasis was put on n-heptyl ether of estrone, which was highly active in the lipid assay but scarcely effective in the uterotrophic test and therefore had a very high lipid-estrogenic ratio by either route of administration. It must be pointed out, however, that the oviductotrophic activity of estrone ethers closely paralleled the lipid-shifting one.