Chemistry:Triphenylbromoethylene

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Triphenylbromoethylene (TPBE; brand names Bromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm), also known as bromotriphenylethylene or as phenylstilbene bromide, is a synthetic nonsteroidal estrogen of the triphenylethylene group that was marketed in the 1940s similarly to the closely related estrogen triphenylchloroethylene.[1][2]

SAR

A diethoxylated derivative of triphenylbromoethylene, estrobin (DBE), is also an estrogen, but, in contrast, was never marketed.[3] An ethylated derivative of triphenylbromoethylene, broparestrol (BDPE), is a selective estrogen receptor modulator (SERM) that has been marketed.[4][5]

Although the vinylic halogens has already been discussed, it was discovered that Triphenylacrylonitrile [6304-33-2] also potently modulates the estrogen receptor.[6][7]

Synthesis and reactions

The synthesis of triphenylbromoethylene has been discussed previously:[8]

Grignard reaction of Triphenylbromoethylene with carbon dioxide gives a compound that is called Triphenylacrylic acid [4452-05-5].[9] The acid can then undergo esterification with Diethylethanolamine [100-37-8] (via the acid chloride for example would work).[10] This agent was claimed to have hormonal activity but was also stated to function as a coronary vasodilator. In terms of the SAR it is counselled to consider an agent that is called Cinnamaverine [1679-75-0].[11] Cinnamaverine has the same structure as the compound just described but differs in that it was made by the esterification of 2,3-diphenylacrylic acid [91-48-5]. By contrast though, Cinnamaverine was claimed to function as a Local anaesthetic, antispasmodic agent.

It does need to be said though that saponification of Triphenylacrylonitrile [6304-33-2] would also yield the Triphenylacrylic acid. It is worth pointing out that this compound was made by a reaction that is called a Knoevenagel condensation.[12] (The related Perkin reaction only works with benzaldehydes and not benzophenones.)

See also

References

  1. ↑ Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. 2001. p. 1861. ISBN 978-3-527-30247-5. https://books.google.com/books?id=zmpqAAAAMAAJ. "C20H15Br. 1607-57-4. Bromotriphenylethene = Triphenylbromoethylene = Phenylstilbene bromide = 1,1',1"-(1-Bromo-1-ethenyl-2-yli- dene)tris[benzene] (•) S Bromylene, Fenbrostilbenum, Oestronyl, Phenylstilbene bromide, Prostilban, Tribenorm U Synthetic estrogen" 
  2. ↑ "Metabolism of the oestrogen triphenylbromoethylene". Nature 163 (4151): 801–802. May 1949. doi:10.1038/163801a0. PMID 18128458. Bibcode: 1949Natur.163..801P. 
  3. ↑ Hormone Assay. Elsevier Science. 22 October 2013. pp. 394–. ISBN 978-1-4832-7286-3. https://books.google.com/books?id=cCzgBAAAQBAJ&pg=PA394. 
  4. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 183–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA183. 
  5. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 139–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA139. 
  6. ↑ "Multivariate analysis by the minimum spanning tree method of the structural determinants of diphenylethylenes and triphenylacrylonitriles implicated in estrogen receptor binding, protein kinase C activity, and MCF7 cell proliferation". Journal of Medicinal Chemistry 35 (3): 573–583. February 1992. doi:10.1021/jm00081a021. https://pubs.acs.org/doi/abs/10.1021/jm00081a021. Retrieved 14 January 2026. 
  7. ↑ "Effect of triphenylacrylonitrile derivatives on estradiol-receptor binding and on human breast cancer cell growth". Journal of Medicinal Chemistry 32 (9): 2092–2103. September 1989. doi:10.1021/jm00129a013. https://pubs.acs.org/doi/abs/10.1021/jm00129a013. 
  8. ↑ "TRIPHENYLVINYLMAGNESIUM BROMIDE". Journal of the American Chemical Society 54 (5): 2045–2048. May 1932. doi:10.1021/ja01344a052. https://pubs.acs.org/doi/abs/10.1021/ja01344a052. 
  9. ↑ "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. https://pubs.acs.org/doi/abs/10.1021/ja01345a046. Retrieved 14 January 2026. 
  10. ↑ Krimmel Carl Peter, U.S. Patent 2,690,442 (1954 to GD Searle LLC).
  11. ↑ Rorig Kurt, U.S. Patent 2,673,853 (1954 to Searle & Co).
  12. ↑ "a,b-DIPHENYLCINNAMONITRILE". Organic Syntheses 31: 52. 1951. doi:10.15227/orgsyn.031.0052. http://orgsyn.org/demo.aspx?prep=CV4P0387. 



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