1403674-64-5

Upstream product

• 67-66-3 chloroform 
• 331-64-6 2-fluoro-4-methoxy-benzaldehyde 

Downstream Products

• 1403674-97-4 C₂₅H₂₀F₃NO₃ 
• 883531-28-0 2-(2-fluoro-4-methoxyphenyl)acetic acid 
• 1403674-65-6 2-(2-fluoro-4-methoxyphenyl)acetic acid chloride 
• 1403674-66-7 1-(4-methoxyphenyl)-2-(2-fluoro-4-methoxyphenyl)-ethane-1-one 
• 1403674-67-8 1,2-bis(2-fluoro-4-methoxyphenyl)-ethane-1-one 
• 1403674-71-4 2-(2-fluoro-4-methoxyphenyl)-1,4-bis(4-methoxyphenyl)-butane-1,4-dione 
• 1403674-73-6 1,2,4-tris(2-fluoro-4-methoxyphenyl)-butane-1,4-dione 
• 1403674-82-7 3-(2-fluoro-4-methoxyphenyl)-2,5-bis(4-methoxyphenyl)-1-propyl-1H-pyrrole 

Relevant academic research and scientific papers

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.