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Synthesis of 4,4′‐Diaminotriphenylmethanes with Potential Selective Estrogen Receptor Modulator (SERM)‐like Activity
Author(s) -
Guedes Gema,
Amesty Ángel,
JiménezMonzón Roberto,
MarreroAlonso Jorge,
Díaz Mario,
FernándezPérez Leandro,
EstévezBraun Ana
Publication year - 2015
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201500148
Subject(s) - selective estrogen receptor modulator , estrogen receptor , chemistry , agonist , estrogen , antagonist , pharmacology , mechanism of action , cell culture , receptor , biochemistry , medicine , endocrinology , biology , breast cancer , cancer , in vitro , genetics
In this study, a series of new 4,4′‐diaminotriphenylmethanes was efficiently synthesized from aromatic aldehydes and 2,5‐dimethoxybenzenamine under microwave irradiation in the presence of Sc(OTf) 3 as a catalyst. Antiproliferative activity was assessed by using the MCF‐7 estrogen receptor (ER)‐positive breast cancer cell line, and antagonist/agonist transcriptional activities were determined. Docking studies and competition studies of triphenylmethanes and radiolabeled estradiol determined that these compounds do not bind the ER, indicating that triphenylmethane‐induced changes in proliferative and transcriptional activities differ from conventional mechanisms of action triggered by other selective ER modulators.