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.G.

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Año: 2000 vol. 504 p. 35 - 50

0166-1280

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.