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
收藏
页码：35 / 50
页数：16
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