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Triphenyliodoethylene

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Triphenyliodoethylene
Clinical data
Other namesTPIE; Iodotriphenylethylene; Phenylstilbene iodide; Triphenylvinyl iodide
Drug classNonsteroidal estrogen
Identifiers
  • (1-iodo-2,2-diphenylethenyl)benzene
CAS Number
PubChemCID
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H15I
Molar mass382.244 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)I)C3=CC=CC=C3
  • 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 asiodotriphenylethylene or asphenylstilbene iodide, as well astriphenylvinyl iodide, is asyntheticnonsteroidal estrogen of thetriphenylethylene group that is related totriphenylchloroethylene andtriphenylbromoethylene and was never marketed.[1][2][3]

SAR

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Although the effect of vinylic halogenation has already been discussed, it was discovered thatTriphenylacrylonitrile [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

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References

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  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. Retrieved14 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.


ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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