Triphenylbromoethylene
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Trade names | Bromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm |
| Other names | TPBE; Tribromophenylethylene; Bromotriphenylethylene; Phenylstilbene bromide; Fenbrostilbenum |
| Drug class | Nonsteroidal estrogen |
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| ECHA InfoCard | 100.015.029 |
| Chemical and physical data | |
| Formula | C20H15Br |
| Molar mass | 335.244 g·mol−1 |
| 3D model (JSmol) | |
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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.)
