- Salicylaldoxime moiety as a phenolic "A-Ring" substitute in estrogen receptor ligands.
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
PMID11708930
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).
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