Estrobin
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| Formula | C24H23BrO2 |
| Molar mass | 423.350 g·mol−1 |
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
[edit]Synthesis
[edit]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
[edit]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
[edit]Further reading
[edit]- Way S (January 1946). "D.B.E. in Treatment of Menopausal Symptoms". British Medical Journal. 1 (4435): 10–1. doi:10.1136/bmj.1.4435.10. PMC 2057841. PMID 20786485.
- Greene R (January 1946). "D.B.E.: A New Synthetic Oestrogen". British Medical Journal. 1 (4435): 9–10. doi:10.1136/bmj.1.4435.9. PMC 2057848. PMID 20786497.
References
[edit]- ^ a b c Jordan VC (1986). Estrogen/antiestrogen Action and Breast Cancer Therapy. Univ of Wisconsin Press. pp. 23–. ISBN 978-0-299-10480-1.
- ^ a b c d Welsh AL (April 1954). "Use of synthetic estrogenic substance chlorotrianisene (TACE) in treatment of acne". Archives of Dermatology. 69 (4): 418–27. 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).
- ^ Koelsch, C. F. (June 1932). "Syntheses with Triarylvinylmagnesium Bromides. Triarylacrylic Acids and the Indones Derived from Them". Journal of the American Chemical Society. 54 (6): 2487–2493. Bibcode:1932JAChS..54.2487K. doi:10.1021/ja01345a046. Retrieved 8 January 2026.
- ^ EL BOROLOSSY AW, BOUTROS M (April 1958). "Pharmacological studies on some synthetic estrogens D.B.E. and ovobrene". Archives Internationales de Pharmacodynamie et de Therapie. 114 (3–4): 282–90. PMID 13534819.
- ^ Charles F Longfellow & Arnold O Jackson, U.S. patent 2,429,556 (1947 to G W CARNRICK Co).
- ^ Ruenitz PC, Bagley JR, Nanavati NT (July 1988). "Synthesis and estrogen receptor selectivity of 1,1-bis(4-hydroxyphenyl)-2-(p-halophenyl)ethylenes". Journal of Medicinal Chemistry. 31 (7): 1471–5. doi:10.1021/jm00402a037. PMID 3385736.
- ^ Gust, R., Schönenberger, H., Range, K.-J., Klement, U., Schneider, M. (November 1993). "Crystal structure and hormonal activity of 1,1-bis(4-hydroxyphenyl)-2-phenylethene". Monatshefte für Chemie - Chemical Monthly. 124 (11–12): 1181–1193. doi:10.1007/BF00810027.