Triphenylethylene

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Triphenylethylene
Identifiers
  • 1,1',1''-(Ethene-1,1,2-triyl)tribenzene
JSmol)
  • C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
  • InChI=1S/C20H16/c1-4-10-17(11-5-1)16-20(18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-16H
  • Key:MKYQPGPNVYRMHI-UHFFFAOYSA-N

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

References

  1. ^
    ISBN 978-1-59259-152-7
    .
  2. ^
    ISBN 978-3-0348-0664-0
    .
  3. ISBN 978-0-19-532357-3
    .
  4. ISBN 978-0-444-62667-7
    .
  5. ISBN 978-3-540-34742-2
    .
  6. PMID 3458960
    .
  7. ^
    PMID 10746941
    .
  8. ^
    PMID 11258977
    .
  9. ISBN 978-0-08-054800-5
    .
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