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

A.M RODRIGUEZ; F. GIANNINI,; F.D.SUVIRE; H.A.BALDONI; R. FURLAN; S.ZACCHINO; G.BEKE; P.MATYUS; ENRIZ R.D.; I.G. CSIZMADIA

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2000 vol. 504 p. 35 - 50

0166-1280

The antifungal activity, measured as minimum inhibitory concentration (MIC) of selected a-substituted acetophenones, showed a linear correlation with the computed enolization energies (DEenolization). This suggested that keto?enol tautomerization plays a significant role in the action mechanism of these a-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.