Document Type

Article

Language

eng

Publication Date

9-5-2018

Publisher

Elsevier

Source Publication

European Journal of Medicinal Chemistry

Source ISSN

0223-5234

Abstract

A short and efficient route to 4-(4-hydroxyphenyl)cycloheptanemethanol was developed, which resulted in the preparation of a mixture of 4 stereoisomers. The stereoisomers were separated by preparative HPLC, and two of the stereoisomers identified by X-ray crystallography. The stereoisomers, as well as a small family of 4-cycloheptylphenol derivatives, were evaluated as estrogen receptor-beta agonists. The lead compound, 4-(4-hydroxyphenyl)cycloheptanemethanol was selective for activating ER relative to seven other nuclear hormone receptors, with 300-fold selectivity for the β over α isoform and with EC50 of 30–50 nM in cell-based and direct binding assays.

Comments

Accepted version. European Journal of Medicinal Chemistry, Vol. 157 (September 5, 2018): 791-804. DOI. © 2018 Elsevier. Used with permission.

Daniel S. Sem was affiliated with Concordia University at the time of publication.

Available for download on Wednesday, September 09, 2020

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