Triphenylethylene

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Triphenylethylene
Triphenylethylene.svg
Names
IUPAC name
1,1',1''-(Ethene-1,1,2-triyl)tribenzene
Identifiers
3D model (JSmol)
ECHA InfoCard 100.000.359 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
Properties
C20H16
Molar mass 256.348 g·mol−1
Appearancewhite solid
Density 1.163 g/cm3 [1]
Melting point 65–67.5 °C (149.0–153.5 °F; 338.1–340.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Triphenylethylene (TPE) is the organic compound with the formula (C6H5)2C=CH(C6H5). It is a colorless solid.

Contents

Synthesis and reactions

The compound is prepared in two steps from benzophenone via the intermediacy of 1,2,2-triphenylethanol. [2] Triphenylethylene reacts with iodine to give 9-phenylphenanthroline. [3] Epoxidation gives the chiral oxirane. [4]

Bioactivity

Triphenylethylene possesses weak estrogenic activity. [5] [6] Its estrogenic effects were discovered in 1937. [7] TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of nonsteroidal estrogens. [8]

TPE is the parent compound of a group of nonsteroidal estrogen receptor ligands. [5] [6] [9] It includes the estrogens chlorotrianisene, desmethylchlorotrianisene, estrobin (DBE), M2613, triphenylbromoethylene, triphenylchloroethylene, triphenyliodoethylene, triphenylmethylethylene; the selective estrogen receptor modulators (SERMs) afimoxifene, brilanestrant, broparestrol, clomifene, clomifenoxide, droloxifene, endoxifen, etacstil, fispemifene, idoxifene, miproxifene, miproxifene phosphate, nafoxidine, ospemifene, panomifene, and toremifene. The antiestrogen ethamoxytriphetol (MER-25) is also closely related, but is technically not a derivative of TPE and is instead a triphenylethanol derivative. The tamoxifen metabolite and aromatase inhibitor norendoxifen is also a TPE derivative. In addition to their estrogenic activity, various TPE derivatives like tamoxifen and clomifene have been found to act as protein kinase C inhibitors. [10]

The affinity of triphenylethylene for the rat estrogen receptor is about 0.002% relative to estradiol. [11] [12] For comparison, the relative binding affinities of derivatives of triphenylethylene were 1.6% for tamoxifen, 175% for afimoxifene (4-hydroxytamoxifen), 15% for droloxifene, 1.4% for toremifene (4-chlorotamoxifen), 0.72% for clomifene, and 0.72% for nafoxidine. [13] [11] [12]

See also

References

  1. ↑ Seki, Tomohiro; Mashimo, Takaki; Ito, Hajime (2020). "Crystal Jumping of Simple Hydrocarbons: Cooling-induced Salient Effect of Bis-, Tri-, and Tetraphenylethene through Anisotropic Lattice Dimension Changes without Thermal Phase Transitions". Chemistry Letters. 49 (2): 174–177. doi:10.1246/cl.190768.
  2. ↑ Adkins, Homer; Zartman, Walter (1937). "Triphenylethylene". Organic Syntheses. 17: 89. doi:10.15227/orgsyn.017.0089.
  3. ↑ Mallory, Frank B.; Wood, Clelia S. (1965). "9-Phenylphenanthrene". Organic Syntheses. 45: 91. doi:10.15227/orgsyn.045.0091.
  4. ↑ Kobayashi, Yuki; Inukai, Sae; Asai, Naoki; Oyamada, Mami; Ikegawa, Shohei; Sugiyama, Yuya; Hamamoto, Hiromi; Shioiri, Takayuki; Matsugi, Masato (2014). "A comparative study of the asymmetric epoxidation of aromatic olefins using the first generation manganese salen epoxidation catalysts and their light fluorous variants: An interesting discovery on the use of benzotrifluoride as a cosolvent". Tetrahedron: Asymmetry. 25 (16–17): 1209–1214. doi:10.1016/j.tetasy.2014.07.003.
  5. 1 2 Dragan YP, Pitot HC (5 February 2010). "The Effect of Triphenylethylene Antiestrogens on Parameters of Multisage Hepatocarcinogenesis in the Rat". In Jordan VD, Furr BJ (eds.). Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. pp. 95–. ISBN   978-1-59259-152-7.
  6. 1 2 Maximov PY, McDaniel RE, Jordan VC (23 July 2013). "Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens". Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 4–. ISBN   978-3-0348-0664-0.
  7. ↑ Li JJ (3 April 2009). "Genesis of Statins". Triumph of the Heart: The Story of Statins. Oxford University Press, USA. pp. 33–. ISBN   978-0-19-532357-3.
  8. ↑ Avendano C, Menendez JC (11 June 2015). "Anticancer Drugs that Modulate Hormone Action". Medicinal Chemistry of Anticancer Drugs. Elsevier Science. pp. 81-131 (87). doi:10.1016/B978-0-444-62649-3.00003-X. ISBN   978-0-444-62667-7.
  9. ↑ Marin F, Barbancho MC (22 September 2006). "Clinical Pharmacology of Selective Estrogen Receptor Modulators (SERMs)". In Cano A, Calaf i Alsina J, Duenas-Diez JL (eds.). Selective Estrogen Receptor Modulators: A New Brand of Multitarget Drugs. Springer Science & Business Media. pp. 52–. ISBN   978-3-540-34742-2.
  10. ↑ O'Brian CA, Liskamp RM, Solomon DH, Weinstein IB (June 1986). "Triphenylethylenes: a new class of protein kinase C inhibitors". Journal of the National Cancer Institute. 76 (6): 1243–1246. doi:10.1093/jnci/76.6.1243. PMID   3458960.
  11. 1 2 Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, et al. (March 2000). "The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands". Toxicological Sciences. 54 (1): 138–153. doi: 10.1093/toxsci/54.1.138 . PMID   10746941.
  12. 1 2 Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, et al. (March 2001). "Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens". Chemical Research in Toxicology. 14 (3): 280–294. doi:10.1021/tx000208y. PMID   11258977.
  13. ↑ Wittliff JL, Kerr II DA, Andres SA (2005). "Estrogens IV: Estrogen-Like Pharmaceuticals". In Wexler P (ed.). Encyclopedia of Toxicology. Vol. Dib–L (2nd ed.). Elsevier. pp. 254–258. doi:10.1016/B0-12-369400-0/01087-5. ISBN   978-0-08-054800-5.
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