Propylpyrazoletriol (original) (raw)

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Chemical compound

Pharmaceutical compound

Propylpyrazoletriol
Identifiers
IUPAC name 4-[2,3-bis(4-hydroxyphenyl)-4-propyl-1H-pyrazol-5-ylidene]cyclohexa-2,5-dien-1-one
CAS Number 263717-53-9
PubChem CID 6095481
ChemSpider 16142497
UNII 0T83Y6JZPF
CompTox Dashboard (EPA) DTXSID9040392 Edit this at Wikidata
Chemical and physical data
Formula C24H22N2O3
Molar mass 386.451 g·mol−1
3D model (JSmol) Interactive image
SMILES CCCC1=C(N(NC1=C2C=CC(=O)C=C2)C3=CC=C(C=C3)O)C4=CC=C(C=C4)O
InChI InChI=1S/C24H22N2O3/c1-2-3-22-23(16-4-10-19(27)11-5-16)25-26(18-8-14-21(29)15-9-18)24(22)17-6-12-20(28)13-7-17/h4-15,25,28-29H,2-3H2,1H3Key:UOSWGERPQQOSHS-UHFFFAOYSA-N

Propylpyrazoletriol (PPT) is a synthetic, nonsteroidal agonist of ERα with 400-fold selectivity over ERβ[1] that is used widely in scientific research to study the function of ERα.[2][3][4] Though originally thought to be highly selective for ERα, PPT has subsequently been found to also act as an agonist of the GPER (GPR30).[5]

  1. ^ Weatherman RV (8 September 2008). "Untangling the Estrogen Receptor Web: Tools to Selectively Study Estrogen‐Binding Receptors". In Ottow E, Weinmann H (eds.). Nuclear Receptors as Drug Targets. Methods and Principles in Medicinal Chemistry. John Wiley & Sons. pp. 47–64 (50). doi:10.1002/9783527623297.ch3. ISBN 978-3-527-62330-3.
  2. ^ Pfaus JG, Jones SL, Flanagan-Cato LM, Blaustein JD (15 November 2014). "Female sexual behavior: Hormonal Priming and Control". In Plant TM, Zeleznik AJ (eds.). Knobil and Neill's Physiology of Reproduction: Two-Volume Set. Vol. 2. Academic Press. pp. 2287-2370 (2311). ISBN 978-0-12-397769-4.
  3. ^ Aguirre C, Jayaraman A, Pike C, Baudry M (December 2010). "Progesterone inhibits estrogen-mediated neuroprotection against excitotoxicity by down-regulating estrogen receptor-β". Journal of Neurochemistry. 115 (5): 1277–87. doi:10.1111/j.1471-4159.2010.07038.x. PMC 3010223. PMID 20977477.
  4. ^ Mann MK (2008). Synthesis of Non-steroidal Estrogen Receptor Proteolysis Targeting Chimeric Molecules (PROTACS) (Ph.D. thesis). University of Illinois at Urbana-Champaign. pp. 11–.
  5. ^ Prossnitz ER, Barton M (May 2014). "Estrogen biology: new insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. PMC 4040308. PMID 24530924.