Chemistry:Triphenyliodoethylene

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Triphenyliodoethylene (TPIE), also known as iodotriphenylethylene or as phenylstilbene iodide, as well as triphenylvinyl iodide, is a synthetic nonsteroidal estrogen of the triphenylethylene group that is related to triphenylchloroethylene and triphenylbromoethylene and was never marketed.[1][2][3]

SAR

Although the effect of vinylic halogenation has already been discussed, it was discovered that Triphenylacrylonitrile [6304-33-2] also potently modulates the estrogen receptor.[4][5] The synthesis of this agent is described in the pendant literature.[6]

See also

References

  1. ↑ "Synthetic oestrogens related to triphenylethylene". Proceedings of the XIth International Congress of Pure and Applied Chemistry: Chemistry in relation to medicine and theropeutics [sic], chemistry in relation to fuel, power and transport. Hepworth. 1947. p. 149. https://books.google.com/books?id=bMMfAQAAMAAJ. "In fact the cestrogenic activity of either triphenylbromoethylene or triphenyliodoethylene (J. 3d. Robson, A. Schonberg and H. A. Fahim)(3) (Table 1) compares with that of triphenylchloroethylene. A True Oestrogen and A Pro-oestrogen." 
  2. ↑ British Abstracts. Bureau of Abstracts. 1952. p. 549. https://books.google.com/books?id=D0E_AAAAYAAJ. "Roughly quantitative data are reported for the antagonism between oestrogens (oestradiol, stilboestrol, doisynolic acid, allenolic acid, and triphenyliodoethylene) and progesterone, methyltestosterone, and testosterone propionate given [...]" 
  3. ↑ Egyptian Veterinary Medical Association (1966). Annual Veterinary Congress, Proceedings. L'Institut Francais d'Archéologie Orientale. p. 392. https://books.google.com/books?id=vztXAAAAYAAJ. "But the synthetic oestrogens tested e.g. stilboesterol, triphenyliodoethylene, diosynolic acid and allenolic acid produce constant inhibition of the uterine motility." 
  4. ↑ 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. https://pubs.acs.org/doi/abs/10.1021/jm00081a021. Retrieved 14 January 2026. 
  5. ↑ Bignon, E.; Pons, M.; Crastes De Paulet, A.; Dore, J. C.; Gilbert, J.; Abecassis, J.; Miquel, J. F.; Ojasoo, T. et al. (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. https://pubs.acs.org/doi/abs/10.1021/jm00129a013. 
  6. ↑ "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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