Conformational, Spectroscopic, and Molecular Dynamics DFT Study of Precursors for New Potential Antibacterial Fluoroquinolone Drugs

被引：29

作者：

Dorotikova, Sandra ^{[1
]}

Plevova, Kristina ^{[2
]}

Bucinsky, Lukas ^{[1
]}

Malcek, Michal ^{[1
]}

Herich, Peter ^{[1
]}

Kuckova, Lenka ^{[1
]}

Bobenicova, Miroslava ^{[1
]}

Soralova, Stanislava ^{[3
]}

Kozisek, Jozef ^{[1
]}

Fronc, Marek ^{[1
]}

Milata, Viktor ^{[2
]}

Dvoranova, Dana ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Fac Chem & Food Technol, Inst Phys Chem & Chem Phys, SK-81237 Bratislava, Slovakia

[2] Slovak Univ Technol Bratislava, Fac Chem & Food Technol, Inst Organ Chem Catalysis & Petrochem, SK-81237 Bratislava, Slovakia

[3] Comenius Univ, Fac Pharm, Dept Pharmaceut Chem, SK-83232 Bratislava, Slovakia

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2014年 / 118卷 / 40期

关键词：

CONSISTENT PERTURBATION-THEORY; AB-INITIO; QUANTUM-THEORY; DNA; QUINOLONES; IMPLEMENTATION; RESISTANCE; RESONANCE; SPECTRA; ATOMS;

D O I：

10.1021/jp506355f

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：

Biological activity, functionality, and synthesis of (fluoro)quinolones is closely related to their precursors (for instance 3-fluoroanilinoethylene derivatives) (i.e., their functional groups, conformational behavior, and/or electronic structure). Herein, the theoretical study of 3-fluoroanilinoethylene derivatives is presented. Impact of substituents (acetyl, methyl ester, and ethyl ester) on the conformational analysis and the spectral behavior is investigated. The B3LYP/6-311++G** computational protocol is utilized. It is found that the intramolecular hydrogen bond N-H center dot center dot center dot O is responsible for the energetic preference of anti (a) conformer (anti position of 3-fluoroanilino group with respect to the C=C double bond). The Boltzmann ratios of the conformers are related to the differences of the particular dipole moments and/or their dependence on the solvent polarity. The studied acetyl, ethyl ester, and methyl ester substituted fluoroquinolone precursors prefer in the solvent either EZa, ZZa, or both conformers equally, respectively. In order to understand the degree of freedom of rotation of the trans ethyl ester group, B3LYP/6-311G** molecular dynamic simulations were carried out. Vibrational frequencies, electron transitions, as well as NMR spectra are analyzed with respect to conformational analysis, including the effect of the substituent. X-ray structures of the precursors are presented and compared with the results of the conformational analysis.

引用

页码：9540 / 9551

页数：12

共 61 条

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