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Salicylaldoxime moiety as a phenolic "A-Ring" substitute in estrogen receptor ligands.

Journal of medicinal chemistry (2001-11-16)
F Minutolo, S Bertini, C Papi, K E Carlson, J A Katzenellenbogen, M Macchia
ABSTRACT

The phenolic "A-ring" of natural and synthetic estrogen receptor (ER) ligands was effectively replaced by a planar six-member ring formed through an intramolecular hydrogen bond within a salicylaldoxime. Thus, oxime 1, a structural analogue of a triarylethylene estrogen, showed a significant binding affinity for the ER. The OH of the oxime function appears to mimic the phenolic OH present in more "classical" ER ligands because the binding reduced when the oxime OH is methylated (2) or absent (3).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Salicylaldoxime, ≥98.0% (NT)