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Related Experiment Videos

17-Desoxy estrogen analogues.

R H Peters1, D F Crowe, M A Avery

  • 1Bio-Organic Chemistry Laboratory, SRI International, Menlo Park, California 94025.

Journal of Medicinal Chemistry
|July 1, 1989
PubMed
Summary
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New 17-desoxyestratrienes show potent postcoital antifertility effects with low estrogenicity. Modifications, including a 17 beta-ethyl side chain and nuclear alterations, enhance this separation for potential contraceptive development.

Area of Science:

  • Medicinal Chemistry
  • Endocrinology
  • Reproductive Biology

Background:

  • Estrogen derivatives are crucial in reproductive health.
  • Developing effective and safe postcoital antifertility agents remains a priority.
  • Previous research indicated a necessity for 17-oxygen functionality in potent estrogenic activity.

Purpose of the Study:

  • To synthesize and evaluate novel 17-substituted, 17-desoxyestratrienes as potential postcoital antifertility agents.
  • To investigate the structure-activity relationships of these compounds regarding antifertility and estrogenic effects.
  • To identify compounds with a high separation ratio between antifertility and estrogenicity.

Main Methods:

  • Synthesis of a series of 17-substituted, 17-desoxyestratrienes.

Related Experiment Videos

  • Determination of estrogen-relative binding affinities.
  • In vivo assays in rats to assess estrogenic and postcoital antifertility activity.
  • Estrogenic activity testing in monkeys for selected compounds.

    • Main Results:

    • Several 17-desoxyestratriene derivatives (8a, 8b, 30) demonstrated potent postcoital antifertility activity in rats with low estrogenic effects.
    • The omission of the 17-oxygen functionality did not impede antifertility potency.
    • A 17 beta-ethyl side chain yielded the highest antifertility activity and separation ratio.
    • Nuclear modifications at positions 7 and 11, particularly an 11-hydroxy moiety, further improved the separation of antifertility from estrogenicity.

    Conclusions:

    • 17-desoxyestratrienes represent a promising class of compounds for postcoital antifertility applications.
    • Structural modifications, specifically the 17 beta-ethyl group and nuclear substitutions, are key to optimizing antifertility efficacy while minimizing estrogenic side effects.
    • These findings challenge previous assumptions about the necessity of 17-oxygen functionality and open new avenues for contraceptive drug design.