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883531-28-0

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Influence of chlorine or fluorine substitution on the estrogenic properties of 1-alkyl-2,3,5-tris(4-hydroxyphenyl)-1H-pyrroles
In continuation of our previous work, several 1-alkyl-2,3,5-tris(4- hydroxyphenyl)aryl-1H-pyrroles with chlorine or fluorine substituents in the aryl residues were synthesized and tested for estrogen receptor (ER) binding at isolated ERα/ERβ receptors (HAP assay) and in transactivation assays using ERα-positive MCF-7/2a as well as U2-OS/ERα and U2-OS/ERβ cells. In the competition experiment at ERα the compounds displayed very high relative binding affinities of up to 37% (determined for 8m) but with restricted subtype selectivity (e.g., ERα/ERβ (8m) = 9). The highest estrogenic potency in ERα-positive MCF-7/2a cells was determined for 2,3,5-tris(2-fluoro-4-hydroxyphenyl)-1-propyl-1H-pyrrole 8m (EC50 = 23 nM), while in U2-OS/ERα cells 2-(2-fluoro-4-hydroxyphenyl)-3,5-bis(4- hydroxyphenyl)-1-propyl-1H-pyrrole 8b (EC50 = 0.12 nM) was the most potent agonist, only 30-fold less active than estradiol (E2, EC50 = 0.004 nM). In U2-OS/ERβ cells for all pyrroles no transactivation could be observed, which indicates that they are selective ERα agonists in cellular systems.
Sch?fer, Anja,Wellner, Anja,Strauss, Martin,Sch?fer, Andreas,Wolber, Gerhard,Gust, Ronald
supporting information
p. 9607 - 9618
(2013/01/16)

Method of treating diabetes and related disease states.
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(2008/06/13)

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Chemical Properties

Boiling Point: 290.6 °C at 760 mmHg
Flash Point:129.5 °C
Density: 1.269 g/cm³
Storage Temp.:Sealed in dry,Room Temperature
Vapor Pressure: 0.000943mmHg at 25°C
Refractive Index: 1.519
PKA: 4.17±0.10(Predicted)
PSA: 46.53000
LogP: 1.46140

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