Design and synthesis of fluorescently labeled steroidal antiestrogens

Steroids
Robert N Hanson, Nisal Gajadeera

Abstract

A set of derivatives of 11β-(4-oxyphenyl)estradiol were prepared as potential fluorescent imaging agents for the evaluation of the estrogen receptor. The compounds were designed based on the established affinity and selectivity of 11β-[4-(dimethylethoxy)phenyl]estradiol (RU39411) as an estrogen receptor (ER) antagonist. The 5-(dimethylamino) naphathalene-1-sulfonyl (dansyl) and 7-nitrobenzo[c][1,2,5] oxadiaol-4-yl (NBD) moieties were selected based on their fluorescent and physicochemical properties. A convergent synthesis was developed that culminated in the [3 + 2] copper (I) assisted alkyne-azide cycloaddition coupling of the steroidal and fluorescent components. Good yields were obtained for the intermediates and final products, and the structural variations in the steroid component will permit evaluation of ER affinity and selectivity.

References

Dec 18, 2003·Drug Discovery Today·Hartmuth C Kolb, K Barry Sharpless
Mar 8, 2007·Journal of the National Cancer Institute·V Craig Jordan
Jan 20, 2012·Bioorganic & Medicinal Chemistry Letters·J Adam HendricksRobert N Hanson
Sep 20, 2012·Bioorganic & Medicinal Chemistry·Krishna P BhabakChristoph Arenz
Sep 26, 2012·Organic & Biomolecular Chemistry·Robert N HansonRobert G Croy
May 8, 2013·Bioorganic & Medicinal Chemistry Letters·J Adam HendricksBrian S Blagg
Jun 4, 2013·Seminars in Nuclear Medicine·Hannah M Linden, Farrokh Dehdashti
Jul 16, 2014·Bioorganic & Medicinal Chemistry·Wanida PhetsangMatthew A Cooper
Aug 26, 2014·ACS Medicinal Chemistry Letters·Jing WuJian-Xin Li
Feb 10, 2019·Steroids·Nisal Gajadeera, Robert N Hanson

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