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Enhanced estrogen receptor beta (ERβ) selectivity of fluorinated carborane-containing ER modulators.

Abstract：

:We previously showed that fluorination of the carborane-containing selective estrogen receptor modulator (SERM) BE360 altered the agonist/antagonist activity balance and the estrogen receptor (ER) α/β subtype selectivity. Here, we designed and synthesized a series of fluorinated carboranyl phenols as candidate ERβ-selective ligands. Introduction of a fluorine atom onto the carborane cage commonly reduced the binding affinity for ERα, to an extent that depended on the other substituents present. The B-fluorinated m-carboranyl phenol 4a showed fourfold more potent ERβ-binding affinity than the parent non-fluorinated compound 7. 1-Iodo-9-fluoro-m-carboranyl phenol 4f showed high ERβ-binding affinity with an ERβ/ERα selectivity ratio of 8.2. Among the compounds tested, 6 showed the highest ERβ selectivity (10.1-fold) and the highest ER-agonistic activity (EC50: 5.1×10(-10) M) in MCF-7 cell proliferation assay.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Ohta K,Ogawa T,Kaise A,Endo Y

doi

10.1016/j.bmcl.2013.10.067

subject

Has Abstract

pub_date

2013-12-15 00:00:00

pages

6555-8

issue

24

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(13)01273-0

journal_volume

23

pub_type

杂志文章

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