Propylpyrazoletriol

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 ;
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,2-3H2,1H3; Key: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]

References

^ 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.
^ 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.
^ 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.
^ 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–.
^ 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.

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[OttowWeinmann2008-1] 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.

[PlantZeleznik2014-2] 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.

[pmid20977477-3] 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–.

[ProssnitzBarton2014-5] 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.

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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
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,2-3H2,1H3 Key:UOSWGERPQQOSHS-UHFFFAOYSA-N

Propylpyrazoletriol

See also

References