3,17 beta-Dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-trienes: synthesis, rearrangement, cytotoxicity, and estrogen-receptor binding.

doi:10.1021/JM00158A039

Paper

3,17 beta-Dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-trienes: synthesis, rearrangement, cytotoxicity, and estrogen-receptor binding.

Published Aug 1, 1986 · J. C. Gill, P. Lockey, B. Marples

Journal of medicinal chemistry

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7

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0

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Abstract

Diastereoisomers of 3,17 beta-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene have been prepared as potential antitumor agents. Both isomers undergo the base-catalyzed Payne rearrangement. The isomers were cytotoxic to mammalian cells in culture and were able to displace [3H]estradiol from binding sites in rat uterine cytosols with 1/7 and 1/70 the potency of estradiol. The reasons for this difference are discussed.

In Vitro Study

Study Snapshot

Diastereoisomers of 3,17 beta-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene show potential as antitumor agents, with 1/7 and 1/70 the potency of estradiol, and undergo Payne rearrangement

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

3,17 beta-Dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-trienes: synthesis, rearrangement, cytotoxicity, and estrogen-receptor binding.

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References

Citations

gem-disubstituent effect: theoretical basis and synthetic applications.

Gem-disubstituent effect has significant synthetic applications and biochemical and pharmaceutical implications, with potential for drug design and synthesis of complex inorganic and organometallic complexes.

Epoxide Migration (Payne Rearrangement) and Related Reactions

Epoxide migration can be a powerful synthetic method for introducing functionality into substrates containing 2,3-epoxy alcohol moiety, but can also be a significant problem when not desired.

The estradiol pharmacophore: Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site

Estradiol's binding site model suggests that all four rings contribute significantly to binding, with small hydrophobic substituents enhancing binding affinity and larger hydrophobic substituents tolerated.

Heterosteroids and drug research.

Heterosteroids are effective drugs for treating various conditions, including anti-inflammatory, anti-progestational, and anti-cancer effects.