Abstract
Summary
The biological properties of some 19-nortestosterone-3-cyclopentyl enol ethers have been studied. The 17α-ethyl analogue resulted in decreased estrogenicity, increased progestational and pregnancy maintenance properties as compared to 17α-methyl and 17α-ethynyl derivatives. The methyl analogue, however, exhibited a considerable increase in androgenicity and greater anovulatory and gonadotropin inhibitory properties when compared to the other compounds, Both the methyl and ethyl substitutions resulted in masculinized female rat fetuses which in the case of the ethyl derivative demonstrated the lack of correlation between this effect and androgenic properties. Unlike the others, the 17α-methyl analogue, exhibited prolonged androgenic activity by either oral or subcutaneous administration. Our findings indicate that the nature of the parent ketone and not enol etheriftcation
The authors wish to thank Mr. Paul Nemith for his technical assistance and Mr. Neil Stasilli for his statistical analysis of the data. We also express our gratitude to Professors Dr. A. Ercoli and Dr. R. Gardi, Steroid Institute, Warner-Vister, 22064 Casatenova Brianza (Como) Italy, for the synthesis at our request of MCPE and ECPE.
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