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

F. Minutolo, S. Bertini, C. Papi, K. E. Carlson, J. A. Katzenellenbogen, M. Macchia

Research output: Contribution to journalArticlepeer-review


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).

Original languageEnglish (US)
Pages (from-to)4288-4291
Number of pages4
JournalJournal of Medicinal Chemistry
Issue number24
StatePublished - Nov 22 2001

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


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