Correlation of antifungal activity of selected α-substituted acetophenones with their keto-enol tautomerization energy

A. M. Rodríguez, F. A. Giannini, F. D. Suvire, H. A. Baldoni, R. Furlán, S. A. Zacchino, G. Beke, P. Mátyus, R. D. Enriz, I. G. Csizmadia

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The antifungal activity, measured as minimum inhibitory concentration (MIC) of selected α-substituted acetophenones, showed a linear correlation with the computed enolization energies (ΔE(enolization)). This suggested that keto-enol tautomerization plays a significant role in the action mechanism of these α-substituted acetophenones. In order to corroborate this conclusion, two related compounds were synthesized which could not undergo keto-enol tautomerization. Their, bioassay proved them to be completely inactive. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)35-50
Number of pages16
JournalJournal of Molecular Structure: THEOCHEM
Publication statusPublished - Jun 12 2000



  • Antifungal activity
  • Conformational- analysis
  • Hartree-Fock and DFT computations
  • Keto-enol tautomerization
  • α-Substituted acetophenones

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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