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
相关论文
共 50 条
  • [11] Keto-Enol Tautomerization as a First Step in Hydrogenation of Carbonyl Compounds
    Attia, Smadar
    Schmidt, Marvin C.
    Schroeder, Carsten
    Weber, Jann
    Baumann, Ann-Katrin
    Schauermann, Swetlana
    JOURNAL OF PHYSICAL CHEMISTRY C, 2019, 123 (48): : 29271 - 29277
  • [12] Structural characterization and keto-enol tautomerization of 4-substituted pyrazolone derivatives with DFT approach
    Eryilmaz, Serpil
    Bagdatli, Emine
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2024, 131
  • [13] Keto-Enol tautomerization of quercetin in solutions of a cationic surfactant, miramistin
    Barvinchenko, V. N.
    Lipkovskaya, N. A.
    Fedyanina, T. V.
    COLLOID JOURNAL, 2014, 76 (01) : 1 - 5
  • [14] Keto-Enol tautomerization of quercetin in solutions of a cationic surfactant, miramistin
    V. N. Barvinchenko
    N. A. Lipkovskaya
    T. V. Fedyanina
    Colloid Journal, 2014, 76 : 1 - 5
  • [15] Post-polymerization modification of polymethacrylates enabled by keto-enol tautomerization
    Easterling, Charles P.
    Coste, Guilhem
    Sanchez, Jose E.
    Fanucci, Gail E.
    Sumerlin, Brent S.
    POLYMER CHEMISTRY, 2020, 11 (17) : 2955 - 2958
  • [16] KETO-ENOL TAUTOMERIZATION RATES OF ACETYLACETONE IN MIXED AQUEOUS-MEDIA
    WATARAI, H
    SUZUKI, N
    JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1974, 36 (08): : 1815 - 1820
  • [17] Enhancement of the reactivity of photochemically generated enediynes via keto-enol tautomerization
    Karpov, Grigori
    Kuzmin, Alexander
    Popik, Vladimir V.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (35) : 11771 - 11777
  • [18] A Theoretical Study on Keto-Enol Tautomerization Involving Simple Carbonyl Derivatives
    J Comput Chem, 1 (56):
  • [19] Keto-enol tautomerization of cyanuric acid in the gas phase and in water and methanol
    Liang, Xiaoqin
    Pu, Xuemei
    Zhou, Hongwei
    Wong, Ning-Bew
    Tian, Aninin
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2007, 816 (1-3): : 125 - 136
  • [20] Accelerated Keto-Enol Tautomerization Kinetics of Malonic Acid in Aqueous Droplets
    Kim, Pyeongeun
    Continetti, Robert E.
    ACS EARTH AND SPACE CHEMISTRY, 2021, 5 (09): : 2212 - 2222
12345