ERbeta ligands. Part 5: synthesis and structure-activity relationships of a series of 4'-hydroxyphenyl-aryl-carbaldehyde oxime derivatives.

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Mewshaw RE, Bowen SM, Harris HA, Xu ZB, Manas ES, Cohn ST

ERbeta ligands. Part 5: synthesis and structure-activity relationships of a series of 4'-hydroxyphenyl-aryl-carbaldehyde oxime derivatives.

Bioorg Med Chem Lett. 2007 Feb 15;17(4):902-6. Epub 2006 Dec 1.

PubMed ID
17188490 [ View in PubMed
]
Abstract

A series of 4'-hydroxyphenyl-aryl-carbaldehyde oximes (5b) was prepared and found to have high affinity (4nM) and modest selectivity (39-fold) for estrogen receptor-beta (ERbeta). Substitution of one of the core rings of the scaffold based around these novel ligands further expanded our knowledge in the quest toward achieving high affinity and selectivity for ERbeta. An X-ray co-crystal of structure 11 revealed that the oxime moiety was mimicking the C-ring of genistein, as previously predicted by SAR and docking studies.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
4-(4-HYDROXYPHENYL)-1-NAPHTHALDEHYDE OXIMEEstrogen receptor betaIC 50 (nM)5N/AN/ADetails
EstradiolEstrogen receptor alphaIC 50 (nM)3.2N/AN/ADetails
EstradiolEstrogen receptor betaIC 50 (nM)3.6N/AN/ADetails
GenisteinEstrogen receptor alphaIC 50 (nM)395N/AN/ADetails
GenisteinEstrogen receptor betaIC 50 (nM)9.7N/AN/ADetails