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• W2123260033 endingPage "803" @default.
• W2123260033 startingPage "794" @default.
• W2123260033 abstract "Abstract In this study, we synthesized 1,2,4‐triarylpyrroles as ligands for the estrogen receptor (ER). Two pyrrole series were prepared with either C3‐alkyl or C3/C5‐dialkyl residues. Compounds from both series were susceptible to oxidative degradation—dialkylated compounds ( t 1/2 =33–66 h) to a higher extent than their monoalkylated congeners ( t 1/2 =140–211 h). Nevertheless, stability was sufficient for determination of in vitro ER binding affinity. The most active agonist in hormone‐dependent, ERα‐positive MCF‐7/2a and U2‐OS/α cells was 1,2,4‐tris(4‐hydroxyphenyl)‐3‐propyl‐1 H ‐pyrrole ( 6 d ) (MCF‐7/2a: EC 50 =70 n M ; U2‐OS/α: EC 50 =1.6 n M ). A corresponding inactivity in U2‐OS/β cells demonstrated the high ERα selectivity. This trend was confirmed in a competition experiment using estradiol (E2) and purified hERα and hERβ proteins (relative binding affinity (RBA) calculated for 6 d : RBA(ERα)=1.85 %; RBA(ERβ) <0.01 %). Generally, C3/C5‐dialkyl substitution led to reduction of activity, possibly due to lower stability." @default.
• W2123260033 created "2016-06-24" @default.
• W2123260033 creator A5004984536 @default.
• W2123260033 creator A5016935807 @default.
• W2123260033 creator A5057876555 @default.
• W2123260033 date "2011-03-17" @default.
• W2123260033 modified "2023-10-16" @default.
• W2123260033 title "Synthesis and Investigations on the Oxidative Degradation of C3/C5-Alkyl-1,2,4-triarylpyrroles as Ligands for the Estrogen Receptor" @default.
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• W2123260033 doi "https://doi.org/10.1002/cmdc.201000537" @default.
• W2123260033 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/21416612" @default.
• W2123260033 hasPublicationYear "2011" @default.
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