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

被引：3

作者：

Rodríguez, AM

Giannini, FA

Suvire, FD

Baldoni, HA

Furlán, R

Zacchino, SA

Beke, G

Mátyus, P

Enriz, RD

Csizmadia, IG

机构：

[1] Univ Nacl San Luis, Dept Quim, RA-5700 San Luis, Argentina

[2] Univ Rosario, Fac Ciencias Bioquim & Farmaceut, Dept Farmacognosia, RA-7000 Rosario, Argentina

[3] Semmelweis Univ, Inst Organ Chem, H-1092 Budapest, Hungary

[4] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2000年 / 504卷

关键词：

antifungal activity; alpha-substituted acetophenones; conformational analysis; Hartree-Fock and DFT computations; keto-enol tautomerization;

D O I：

10.1016/S0166-1280(00)00353-5

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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

引用

页码：35 / 50

页数：16

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