Chemistry:Triphenylethylene

From HandWiki

Triphenylethylene (TPE) is the organic compound with the formula (C
6H
5)
2C=CH(C
6H
5). It is a colorless solid.

Synthesis and reactions

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

Bioactivity

Triphenylethylene possesses weak estrogenic activity.[4][5] Its estrogenic effects were discovered in 1937.[6] TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of nonsteroidal estrogens.[7]

TPE is the parent compound of a group of nonsteroidal estrogen receptor ligands.[4][5][8] 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.[9]

The affinity of triphenylethylene for the rat estrogen receptor is about 0.002% relative to estradiol.[10][11] 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.[12][10][11]

See also

References

  1. ↑ Adkins, Homer; Zartman, Walter (1937). "Triphenylethylene". Organic Syntheses 17: 89. doi:10.15227/orgsyn.017.0089. 
  2. ↑ Mallory, Frank B.; Wood, Clelia S. (1965). "9-Phenylphenanthrene". Organic Syntheses 45: 91. doi:10.15227/orgsyn.045.0091. 
  3. ↑ Kobayashi, Yuki; Inukai, Sae; Asai, Naoki; Oyamada, Mami; Ikegawa, Shohei; Sugiyama, Yuya; Hamamoto, Hiromi; Shioiri, Takayuki et al. (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. 
  4. ↑ 4.0 4.1 "The Effect of Triphenylethylene Antiestrogens on Parameters of Multisage Hepatocarcinogenesis in the Rat". Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. 5 February 2010. pp. 95–. ISBN 978-1-59259-152-7. https://books.google.com/books?id=dM0uvBnxiN0C&pg=PA95. 
  5. ↑ 5.0 5.1 "Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens". Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. 23 July 2013. pp. 4–. ISBN 978-3-0348-0664-0. https://books.google.com/books?id=p-W5BAAAQBAJ&pg=PA4. 
  6. ↑ "Genesis of Statins". Triumph of the Heart: The Story of Statins. Oxford University Press, USA. 3 April 2009. pp. 33–. ISBN 978-0-19-532357-3. https://books.google.com/books?id=-GPl1PA5EgMC&pg=PA33. 
  7. ↑ "Anticancer Drugs that Modulate Hormone Action". Medicinal Chemistry of Anticancer Drugs. Elsevier Science. 11 June 2015. pp. 81-131 (87). doi:10.1016/B978-0-444-62649-3.00003-X. ISBN 978-0-444-62667-7. https://books.google.com/books?id=VEibBwAAQBAJ&pg=PA87. 
  8. ↑ "Clinical Pharmacology of Selective Estrogen Receptor Modulators (SERMs)". Selective Estrogen Receptor Modulators: A New Brand of Multitarget Drugs. Springer Science & Business Media. 22 September 2006. pp. 52–. ISBN 978-3-540-34742-2. https://books.google.com/books?id=heJDAAAAQBAJ&pg=PA52. 
  9. ↑ "Triphenylethylenes: a new class of protein kinase C inhibitors". Journal of the National Cancer Institute 76 (6): 1243–1246. June 1986. doi:10.1093/jnci/76.6.1243. PMID 3458960. 
  10. ↑ 10.0 10.1 "The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands". Toxicological Sciences 54 (1): 138–153. March 2000. doi:10.1093/toxsci/54.1.138. PMID 10746941. 
  11. ↑ 11.0 11.1 "Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens". Chemical Research in Toxicology 14 (3): 280–294. March 2001. doi:10.1021/tx000208y. PMID 11258977. 
  12. ↑ "Estrogens IV: Estrogen-Like Pharmaceuticals". Encyclopedia of Toxicology. Dib-L (2nd ed.). Elsevier. 2005. pp. 254–258. doi:10.1016/B0-12-369400-0/01087-5. ISBN 978-0-08-054800-5. https://books.google.com/books?id=dEnbcGW44RYC&pg=PT3318. 



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