Effect of fluorination on the pharmacological profile of 11beta isomers of fulvestrant in breast carcinoma cells

Journal of Medicinal Chemistry
Vangelis AgouridasGuy Leclercq

Abstract

We describe the synthesis of an 11beta isomer 3 of the steroidal antiestrogen fulvestrant 2. Partial fluorination of the 11beta side chain in 3 leads to 4, which still shows strong antiproliferative activity on MCF-7 cells. However, unlike 2 and 3, compound 4 fails to down-regulate estrogen receptor alpha (ERalpha). This result suggests that ERalpha down-regulation is not a sine qua non condition for the antitumor activity of steroidal antiestrogens.

References

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Dec 23, 2003·Best Practice & Research. Clinical Endocrinology & Metabolism·Sacha J HowellAnthony Howell
Apr 20, 2004·British Journal of Cancer·C K OsborneR I Nicholson
Jan 21, 2006·Molecular Endocrinology·Elaine T Alarid
Jul 28, 2006·Bioorganic & Medicinal Chemistry·Vangelis AgouridasGuy Leclercq
Sep 7, 2006·Endocrine-related Cancer·Anthony Howell
Apr 5, 2008·Molecular Endocrinology·Nicholas B BerryKenneth P Nephew

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Citations

Jun 4, 2013·The Journal of Steroid Biochemistry and Molecular Biology·Atul GuptaArvind S Negi
Jul 2, 2015·Chemistry : a European Journal·Xuan WangMasanobu Uchiyama
Nov 10, 2018·Journal of Medicinal Chemistry·Benjamin JeffriesBruno Linclau

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