Chemistry:Estrobin
Estrobin, also known as α,α-di(p-ethoxyphenyl)-β-phenylbromoethylene and commonly abbreviated as DBE, is a synthetic, nonsteroidal estrogen of the triphenylethylene group that was never marketed.[1][2] Chlorotrianisene, and subsequently clomifene and tamoxifen, were derived from it.[1][2] Estrobin, similarly to other triphenylethylenes, is very lipophilic and hence very long-lasting in its duration of action.[1][2] Similarly to chlorotrianisene, estrobin behaves as a prodrug to a much more potent estrogen in the body.[2]
Chemistry
Synthesis
The chemical synthesis of estrobin has been described:[3][4]
Grignard reaction between two equivalents of 4-bromophenetole (1) and ethyl phenylacetate (2) gives 1,1-bis(4-ethoxyphenyl)-2-phenylethanol (3). Treatment with molecular bromine in glacial acetic acid then completes the synthesis of estrobin (5).
Related compounds
Other bromotriphenylethylenes with estrogenic activity include M2613, oeplexyl, and ovobrene.[5][6]
The chief metabolite is thought to elicit a stronger degree of estrogenicity than estrobin itself.[7][8] This analogy is like comparing methoxychlor to HPTE. In the SAR study that followed, it was elucidated that an olefinic (aka vinylic) halogen atom is not in fact actually requisite for there to be a high degree of binding to the estrogen receptor. However, in later work it was confirmed that BHPE proved to be a weak "impeded" estrogen with minor antiestrogenic potency.[9]
See also
Further reading
- "D.B.E. in Treatment of Menopausal Symptoms". British Medical Journal 1 (4435): 10–1. January 1946. doi:10.1136/bmj.1.4435.10. PMID 20786485.
- "D.B.E.: A New Synthetic Oestrogen". British Medical Journal 1 (4435): 9–10. January 1946. doi:10.1136/bmj.1.4435.9. PMID 20786497.
References
- ↑ 1.0 1.1 1.2 Jordan, Virgil Craig (1986). Estrogen/antiestrogen Action and Breast Cancer Therapy. Univ of Wisconsin Press. pp. 23–. ISBN 978-0-299-10480-1. https://books.google.com/books?id=7WmLZfGXST0C&pg=PA23.
- ↑ 2.0 2.1 2.2 2.3 "Use of synthetic estrogenic substance chlorotrianisene (TACE) in treatment of acne". Archives of Dermatology 69 (4): 418–27. April 1954. doi:10.1001/archderm.1954.01540160020004. PMID 13147544.
- ↑ Donald Hey and Philip Carter, GB586493 (1947 to BRITISH SCHERING RES LAB Ltd).
- ↑ Frederick Robert Basford, GB567807 (1945 to Imperial Chemical Industries Ltd).
- ↑ "Syntheses with Triarylvinylmagnesium Bromides. Triarylacrylic Acids and the Indones Derived from Them". Journal of the American Chemical Society 54 (6): 2487–2493. June 1932. doi:10.1021/ja01345a046. Bibcode: 1932JAChS..54.2487K. https://pubs.acs.org/doi/abs/10.1021/ja01345a046. Retrieved 8 January 2026.
- ↑ "Pharmacological studies on some synthetic estrogens D.B.E. and ovobrene". Archives Internationales de Pharmacodynamie et de Therapie 114 (3–4): 282–90. April 1958. PMID 13534819.
- ↑ Charles F Longfellow & Arnold O Jackson, U.S. Patent 2,429,556 (1947 to G W CARNRICK Co).
- ↑ "Synthesis and estrogen receptor selectivity of 1,1-bis(4-hydroxyphenyl)-2-(p-halophenyl)ethylenes". Journal of Medicinal Chemistry 31 (7): 1471–5. July 1988. doi:10.1021/jm00402a037. PMID 3385736.
- ↑ "Crystal structure and hormonal activity of 1,1-bis(4-hydroxyphenyl)-2-phenylethene". Monatshefte für Chemie - Chemical Monthly 124 (11–12): 1181–1193. November 1993. doi:10.1007/BF00810027. http://link.springer.com/10.1007/BF00810027.
 |  |
