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. Csizmadia

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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
Volume504
DOIs
Publication statusPublished - Jun 12 2000

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Acetophenones
bioassay
Bioassay
Microbial Sensitivity Tests
Biological Assay
energy

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Correlation of antifungal activity of selected α-substituted acetophenones with their keto-enol tautomerization energy. / Rodríguez, A. M.; Giannini, F. A.; Suvire, F. D.; Baldoni, H. A.; Furlán, R.; Zacchino, S. A.; Beke, G.; Mátyus, P.; Enriz, R. D.; Csizmadia, I.

In: Journal of Molecular Structure: THEOCHEM, Vol. 504, 12.06.2000, p. 35-50.

Research output: Contribution to journalArticle

Rodríguez, A. M. ; Giannini, F. A. ; Suvire, F. D. ; Baldoni, H. A. ; Furlán, R. ; Zacchino, S. A. ; Beke, G. ; Mátyus, P. ; Enriz, R. D. ; Csizmadia, I. / Correlation of antifungal activity of selected α-substituted acetophenones with their keto-enol tautomerization energy. In: Journal of Molecular Structure: THEOCHEM. 2000 ; Vol. 504. pp. 35-50.
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AU - Baldoni, H. A.

AU - Furlán, R.

AU - Zacchino, S. A.

AU - Beke, G.

AU - Mátyus, P.

AU - Enriz, R. D.

AU - Csizmadia, I.

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