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Ultrasound‐Promoted Synthesis of 2,3‐Bis(4‐hydroxyphenyl)indole Derivatives as Inherently Fluorescent Ligands for the Estrogen Receptor
Author(s) -
Koulocheri Sophia D.,
Haroutounian Serkos A.
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:9<1723::aid-ejoc1723>3.0.co;2-k
Subject(s) - chemistry , indole test , fluorescence , intramolecular force , solvent polarity , binding affinities , estrogen receptor , solvent , receptor , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , medicine , physics , quantum mechanics , cancer , breast cancer
A series of 2,3‐bis(4‐hydroxyphenyl)indole derivatives 4c − f was prepared by ultrasound‐promoted intramolecular cyclodehydration of a polyphosphoric acid solution of α‐anilinyl‐ (or 3‐anisidyl)desoxyanisoins 2c − f , and their optical spectroscopy and estrogen receptor (ER) binding properties were studied. Compounds 4c − f give intense long‐wavelength fluorescent emission, sensitive to solvent polarity and pH. Furthermore, the two indol‐6‐ols 4e , f display reasonably good binding affinities to ER and appear to be well suited for use as fluorescent probes for the detection of ER in cells.