Chemistry:Triphenylethylene
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| Formula | C20H16 |
| Molar mass | 256.348 g·mol−1 |
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Triphenylethylene (TPE) is a simple aromatic hydrocarbon that possesses weak estrogenic activity.[1][2] Its estrogenic effects were discovered in 1937.[3] TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of nonsteroidal estrogens.[4]
TPE is the parent compound of a group of nonsteroidal estrogen receptor ligands.[1][2][5] 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.[6]
The affinity of triphenylethylene for the rat estrogen receptor is about 0.002% relative to estradiol.[7][8] 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.[9][7][8]
See also
- List of SERMs
- Benzothiophene – parent compound for another group of nonsteroidal SERMs that includes raloxifene
- Phenanthrene – parent compound of steroidal estrogens like estradiol
- Chrysene – parent compound of a group of nonsteroidal weak estrogens that includes 2,8-DHHHC and tetrahydrochrysene
- Doisynolic acid – parent compound of a group of nonsteroidal estrogens that includes doisynoestrol
- Allenolic acid – parent compound of a group of nonsteroidal estrogens that includes methallenestril
References
- ↑ 1.0 1.1 "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.
- ↑ 2.0 2.1 "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.
- ↑ "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.
- ↑ "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.
- ↑ "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.
- ↑ "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.
- ↑ 7.0 7.1 "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.
- ↑ 8.0 8.1 "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.
- ↑ "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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