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11 beta-nitrate estrane analogues: potent estrogens
R H Peters1, D F Crowe, M A Avery
1Bio-Organic Chemistry Laboratory, SRI International, Menlo Park, California 94025.
Journal of Medicinal Chemistry
|October 1, 1989
Summary
New estrane derivatives were synthesized and tested for estrogenic and antifertility activity. Several 11 beta-nitrate compounds showed potent oral activity, outperforming ethynylestradiol.
Area of Science:
- Organic Chemistry
- Endocrinology
- Pharmacology
Background:
- Estrane derivatives are crucial in hormonal research and drug development.
- Understanding structure-activity relationships is key for developing novel therapeutics.
- Ethynylestradiol is a widely used synthetic estrogen.
Purpose of the Study:
- To synthesize novel 11 beta-nitratoestranes.
- To evaluate the estrogenic and postcoital antifertility activities of these compounds.
- To compare their efficacy against ethynylestradiol.
Main Methods:
- Selective functionalization of estrane derivatives using cerium ammonium nitrate (CAN).
- Deoxygenation at C-9 using triethylsilane/boron trifluoride etherate.
- In vitro and in vivo assays for estrogenic and antifertility effects.
Main Results:
- Efficient synthesis of 9 alpha,11 beta-defunctionalized estrane derivatives.
- Successful preparation of target 11 beta-nitratoestranes.
- Compounds 2c, 2d, and 3b exhibited potent oral estrogenic and antifertility activity.
- These novel compounds demonstrated superior oral activity compared to ethynylestradiol.
Conclusions:
- The developed synthetic route provides access to novel 11 beta-nitratoestranes.
- The synthesized compounds possess significant estrogenic and postcoital antifertility properties.
- These findings suggest potential therapeutic applications for the novel estrane derivatives.