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ID: ALA1138654

Journal: Bioorg Med Chem Lett

Title: Ring nitrogen-substituted non-steroidal estrogens: pyridine and pyrimidine analogs of the phenol in deoxyhexestrol experience resonance constraints on preferred ligand conformation.

Authors: De Angelis M, Katzenellenbogen JA.

Abstract: To develop compounds selective for estrogen receptor beta (ERbeta), we substituted hydroxypyridine and pyrimidine heteroaryl groups for the characteristic phenol ring of non-steroidal estrogens. The unexpectedly low affinity showed by some of these compounds is ascribed, in part, to a resonance-enforced conformational constraint that prevents their optimal accommodation in the ER ligand binding pocket.

CiteXplore: 15501051

DOI: 10.1016/j.bmcl.2004.09.048