Triphenyliodoethylene

Triphenyliodoethylene

Clinical data
Other names	TPIE; Iodotriphenylethylene; Phenylstilbene iodide; Triphenylvinyl iodide
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name (1-iodo-2,2-diphenylethenyl)benzene
CAS Number	22021-09-6  Y
PubChem CID	12139089
CompTox Dashboard (EPA)	DTXSID201337054
Chemical and physical data
Formula	C20H15I
Molar mass	382.244 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)I)C3=CC=CC=C3
InChI InChI=1S/C20H15I/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:DVJCEGLTPUEWNX-UHFFFAOYSA-N

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

• Broparestrol
• Chlorotrianisene
• Estrobin

References

1. Tadros W (1947). "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. p. 149. 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. Burton TF (1952). British Abstracts. Bureau of Abstracts. p. 549. 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. 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 . 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., 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.
6. "a,b-DIPHENYLCINNAMONITRILE". Organic Syntheses. 31: 52. 1951. doi:10.15227/orgsyn.031.0052.