Triphenylbromoethylene

Last updated
Triphenylbromoethylene
Triphenylbromoethylene.png
Clinical data
Trade names Bromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm
Other namesTPBE; Tribromophenylethylene; Bromotriphenylethylene; Phenylstilbene bromide; Fenbrostilbenum
Drug class Nonsteroidal estrogen
Identifiers
  • (1-bromo-2,2-diphenylethenyl)benzene
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.015.029 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H15Br
Molar mass 335.244 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Br)C3=CC=CC=C3
  • InChI=1S/C20H15Br/c21-20(18-14-8-3-9-15-18)19(16-10-4-1-5-11-16)17-12-6-2-7-13-17/h1-15H
  • Key:VUQVJIUBUPPCDB-UHFFFAOYSA-N

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]

Contents

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. ↑ Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1861. ISBN   978-3-527-30247-5. 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. ↑ Paterson E, Gilbert CW (May 1949). "Metabolism of the oestrogen triphenylbromoethylene". Nature. 163 (4151): 801–802. Bibcode:1949Natur.163..801P. doi:10.1038/163801a0. PMID   18128458. S2CID   13052481.
  3. ↑ Emmens CW (22 October 2013). Hormone Assay. Elsevier Science. pp. 394–. ISBN   978-1-4832-7286-3.
  4. ↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 183–. ISBN   978-1-4757-2085-3.
  5. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 139–. ISBN   978-3-88763-075-1.
  6. ↑ Dore, J. C., Gilbert, J., Bignon, E., Crastes De Paulet, A., Ojasoo, T., Pons, M., Raynaud, J. P., Miquel, J. F. (February 1992). "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. doi:10.1021/jm00081a021 . Retrieved 14 January 2026.
  7. ↑ Bignon, E., Pons, M., Crastes De Paulet, A., Dore, J. C., Gilbert, J., Abecassis, J., Miquel, J. F., Ojasoo, T., Raynaud, J. P. (September 1989). "Effect of triphenylacrylonitrile derivatives on estradiol-receptor binding and on human breast cancer cell growth". Journal of Medicinal Chemistry. 32 (9): 2092–2103. doi:10.1021/jm00129a013.
  8. ↑ Koelsch, C. F. (May 1932). "TRIPHENYLVINYLMAGNESIUM BROMIDE". Journal of the American Chemical Society. 54 (5): 2045–2048. doi:10.1021/ja01344a052.
  9. ↑ 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. doi: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.
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