Synthetic Œstrogenic Agents without the Phenanthrene Nucleus

@article{Dodds1936SyntheticA,
  title={Synthetic {\OE}strogenic Agents without the Phenanthrene Nucleus},
  author={Edward Charles Dodds and W R Lawson},
  journal={Nature},
  year={1936},
  volume={137},
  pages={996-996}
}
THE preparation and physiological properties of synthetic œstrogenic agents were first described in these columns and elsewhere1,2,3. The active compounds described in these publications were derivatives of phenanthrene or 1:2:5:6-dibenzanthracene, and it was noted that at the time of writing no active substances had been discovered which did not contain the phenanthrene nucleus. 
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A Simple Aromatic (Œstrogenic Agent with an Activity of the Same Order as that of Œstrone
TLDR
This work has shown that the phenan-threne nucleus is not an essential part in the molecule of an œstrogenic substance1, and further experiments with compounds of this type have been made, and the following table indicates the potency of some new substances.
Possibilities in the Realm of Synthetic Estrogens
Diphenyl Compounds and Mammary Growth
DODDS and Lawson1 have found that it is possible to obtain the œstrus response in castrated animals with substances which do not contain the phenanthrene nucleus. Various dihydroxydiphenyl compounds…
Impurities in industrial grade 4,4'-isopropylidene diphenol (bisphenol A): possible implications for estrogenic activity.
Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens
TLDR
The application of synthetic organic chemistry to establish the simplest basic structure of estrogenic compounds was a major triumph for medicinal chemistry in the 1930s and would evolve into the nonsteroidal antiestrogens that in the 1960s were predicted to be potential postcoital contraceptives in women based on compelling rodent studies.
Structural Features of Alkylphenolic Chemicals Associated with Estrogenic Activity*
TLDR
The aim of this project was to identify the important structural features responsible for the estrogenic activity of AP chemicals by incubating APs with different structural features in a medium containing a previously described estrogen-inducible strain of yeast expressing the human estrogen receptor.
Expanding the structural footprint of xenoestrogens
Many synthetic chemicals with structural similarity to estradiol bind to the estrogen receptor and disrupt the normal estrogen physiology in humans and other vertebrates. Most of these xenoestrogens…
Bisphenol-A: a new diabetogenic factor?
TLDR
In rodents it has been demonstrated that small doses of bisphenol-A have profound effects on glucose metabolism, and altered blood glucose homeostasis may enhance the development of type 2 diabetes.
Microbial metabolism of the environmental estrogen bisphenol A
TLDR
Preliminary microbial metabolism studies of bisphenol A (BPA) on twenty six microorganisms have shown that Aspergillus fumigatus is capable of metabolizing BPA, and its structure was established as bispenol A-O-β-D-glucopyranoside ( BPAG) based on spectroscopic analyses.
Re-evaluation of the first synthetic estrogen, 1-keto-1,2,3, 4-tetrahydrophenanthrene, and bisphenol A, using both the ovariectomised rat model used in 1933 and additional assays.
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References

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The Oestrogenic Activity of some Condensed-Ring Compounds in Relation to their other Biological Activities
TLDR
Investigations have brought to light a number of pure synthetic compounds, of known molecular structure, which show this physiological activity, and in some of the compounds studied the activity is of a very high order.
A Synthetic Oestrus-Exciting Compound
TLDR
Ketohydroxy-oestrin is possibly represented by formula (i) in conformity with the hypothesis that the ovarian hormones are formed by degradation of sterols, and in the light of recent developments in the chemistry of the sterols.
Sex Hormones and Cancer-Producing Compounds
TLDR
It seems probable that the formation of a carcinogenic compound from a sterol would involve dehydrogenation to the aromatic state, for reduction of 1:2:5: 6-dibenzanthracene to an octahydro compound results in loss of carcinogenic activity.
Observations on the standardization of the water‐soluble, œstrus‐producing hormone