Synthesis and characterization of azole isoflavone inhibitors of aromatase

John C. Hackett, Young Woo Kim, Bin Su, Robert W. Brueggemeier

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

The synthesis and biological evaluation of a series of 2-azole and 2-thioazole isoflavones as potential aromatase inhibitors are described. Differences in inhibitory activity of triazole and imidazole inhibitors are rationalized with density functional theory to expose a key difference in the electronic structure of these molecules. In addition, difference binding spectra of inhibitors to immunoaffinity-purified aromatase produces classical Type II spectra consistent with coordination of the nitrogen lone pair electrons to the aromatase P450 heme.

Original languageEnglish
Pages (from-to)4063-4070
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number12
DOIs
StatePublished - 2 Jun 2005

Keywords

  • Aromatase
  • Density functional theory
  • Difference spectra
  • Inhibitors
  • Isoflavones

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