803733-32-6Relevant articles and documents
Ring nitrogen-substituted non-steroidal estrogens: Pyridine and pyrimidine analogs of the phenol in deoxyhexestrol experience resonance constraints on preferred ligand conformation
De Angelis, Meri,Katzenellenbogen, John A.
, p. 5835 - 5839 (2007/10/03)
Pyridine and pyrimidine analogs of the non-steroidal estrogen deoxyhexestrol were synthesized. Their low affinity for the estrogen receptor is ascribed, in part, to resonance enforcement of a conformation unfavorable for binding. To develop compounds selective for estrogen receptor beta (ERβ), 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.
