Ring structure and aromatic substituent effects on the p K a of the benzoxaborole pharmacophore

John W. Tomsho, Arnab Pal, Dennis G. Hall, Stephen J. Benkovic

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Abstract

In this work, we present an investigation into the physical properties of a unique class of aromatic boronic acids, the benzoxaboroles. Using spectrophotometric methods, the ionization constants of a family of substituted benzoxaboroles are determined. Heterocyclic ring modifications are examined to determine their effects on the ionization of the boronic acid moiety. It is also shown that the substituent effects about the aromatic ring follow a Hammett relationship with the compounds' measured pK a values. Finally, these substituent effects are also shown to extend to the sugar binding properties of these compounds under physiologically relevant conditions. Combined, these data will inform medicinal chemists wishing to tailor the ionization and/or ability of this class of compound to bind diol-containing biomolecules.

Original languageEnglish (US)
Pages (from-to)48-52
Number of pages5
JournalACS Medicinal Chemistry Letters
Volume3
Issue number1
DOIs
StatePublished - Jan 12 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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