triphenylethylene

The compound is prepared in two steps from benzophenone via the intermediacy of 1,2,2-triphenylethanol.{{cite journal |doi=10.15227/orgsyn.017.0089 |title=Triphenylethylene |journal=Organic Syntheses |date=1937 |volume=17 |page=89|first1=Homer|last1=Adkins|first2=Walter|last2=Zartman

}} Triphenylethylene reacts with iodine to give 9-phenylphenanthroline.{{cite journal |doi=10.15227/orgsyn.045.0091 |title=9-Phenylphenanthrene |journal=Organic Syntheses |date=1965 |volume=45 |page=91|first1=Frank B.|last1=Mallory|first2=Clelia S. |last2=Wood }} Epoxidation gives the chiral oxirane.{{cite journal |doi=10.1016/j.tetasy.2014.07.003 |title=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 |date=2014 |last1=Kobayashi |first1=Yuki |last2=Inukai |first2=Sae |last3=Asai |first3=Naoki |last4=Oyamada |first4=Mami |last5=Ikegawa |first5=Shohei |last6=Sugiyama |first6=Yuya |last7=Hamamoto |first7=Hiromi |last8=Shioiri |first8=Takayuki |last9=Matsugi |first9=Masato |journal=Tetrahedron: Asymmetry |volume=25 |issue=16–17 |pages=1209–1214 }}

Triphenylethylene possesses weak estrogenic activity.{{cite book| vauthors = Dragan YP, Pitot HC | chapter = The Effect of Triphenylethylene Antiestrogens on Parameters of Multisage Hepatocarcinogenesis in the Rat | veditors = Jordan VD, Furr BJ |title=Hormone Therapy in Breast and Prostate Cancer| chapter-url = https://books.google.com/books?id=dM0uvBnxiN0C&pg=PA95 |date=5 February 2010|publisher=Springer Science & Business Media|isbn=978-1-59259-152-7|pages=95–}}{{cite book| vauthors = Maximov PY, McDaniel RE, Jordan VC | chapter = Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens |title=Tamoxifen: Pioneering Medicine in Breast Cancer|chapter-url=https://books.google.com/books?id=p-W5BAAAQBAJ&pg=PA4 |date=23 July 2013|publisher=Springer Science & Business Media|isbn=978-3-0348-0664-0|pages=4–}} Its estrogenic effects were discovered in 1937.{{cite book| vauthors = Li JJ | chapter = Genesis of Statins |title=Triumph of the Heart: The Story of Statins| chapter-url = https://books.google.com/books?id=-GPl1PA5EgMC&pg=PA33|date=3 April 2009|publisher=Oxford University Press, USA|isbn=978-0-19-532357-3|pages=33–}} TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of nonsteroidal estrogens.{{cite book| vauthors = Avendano C, Menendez JC | chapter = Anticancer Drugs that Modulate Hormone Action |title=Medicinal Chemistry of Anticancer Drugs| chapter-url = https://books.google.com/books?id=VEibBwAAQBAJ&pg=PA87 |date=11 June 2015|publisher=Elsevier Science|isbn=978-0-444-62667-7|pages= 81-131 (87) | doi = 10.1016/B978-0-444-62649-3.00003-X }}

TPE is the parent compound of a group of nonsteroidal estrogen receptor ligands.{{cite book| vauthors = Marin F, Barbancho MC | chapter = Clinical Pharmacology of Selective Estrogen Receptor Modulators (SERMs)| veditors = Cano A, Calaf i Alsina J, Duenas-Diez JL |title=Selective Estrogen Receptor Modulators: A New Brand of Multitarget Drugs| chapter-url = https://books.google.com/books?id=heJDAAAAQBAJ&pg=PA52|date=22 September 2006|publisher=Springer Science & Business Media|isbn=978-3-540-34742-2|pages=52–}} 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.{{cite journal | vauthors = O'Brian CA, Liskamp RM, Solomon DH, Weinstein IB | title = Triphenylethylenes: a new class of protein kinase C inhibitors | journal = Journal of the National Cancer Institute | volume = 76 | issue = 6 | pages = 1243–1246 | date = June 1986 | pmid = 3458960 | doi = 10.1093/jnci/76.6.1243 }}

The affinity of triphenylethylene for the rat estrogen receptor is about 0.002% relative to estradiol.{{cite journal | vauthors = Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM | display-authors = 6 | title = The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands | journal = Toxicological Sciences | volume = 54 | issue = 1 | pages = 138–153 | date = March 2000 | pmid = 10746941 | doi = 10.1093/toxsci/54.1.138 | doi-access = free }}{{cite journal | vauthors = Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, Hass BS, Xie Q, Dial SL, Moland CL, Sheehan DM | display-authors = 6 | title = Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens | journal = Chemical Research in Toxicology | volume = 14 | issue = 3 | pages = 280–294 | date = March 2001 | pmid = 11258977 | doi = 10.1021/tx000208y }} 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.{{cite book | vauthors = Wittliff JL, Kerr II DA, Andres SA | year = 2005 | chapter = Estrogens IV: Estrogen-Like Pharmaceuticals | veditors = Wexler P | title = Encyclopedia of Toxicology | edition = 2nd | volume = Dib-L | pages = 254–258 |publisher=Elsevier | isbn = 978-0-08-054800-5 | chapter-url = https://books.google.com/books?id=dEnbcGW44RYC&pg=PT3318 | doi = 10.1016/B0-12-369400-0/01087-5 }}

• List of selective estrogen receptor modulators

{{Reflist}}

{{Estrogen receptor modulators}}

Category:Selective estrogen receptor modulators

Category:Synthetic estrogens