Conformational preferences of tolfenamic acid in DMSO-CO2 solvent system by 2D NOESY

被引：18
作者：
Belov, K. V. [1 ]
Dyshin, A. A. [1 ]
Krestyaninov, M. A. [1 ]
Efimov, S. V. [2 ]
Khodov, I. A. [1 ]
Kiselev, M. G. [1 ]
机构：
[1] Russian Acad Sci, GA Krestov Inst Solut Chem, Ivanovo 153045, Russia
[2] Kazan Fed Univ, Inst Phys, Kazan 420008, Russia
来源：
JOURNAL OF MOLECULAR LIQUIDS | 2022年 / 367卷
基金：
俄罗斯科学基金会;
关键词：
Supercritical fluid; Tolfenamic acid; Fenamates; Conformers; Fluid -state NMR; 2D NOESY; PHARMACEUTICAL SOLID POLYMORPHISM; SEMIEMPIRICAL METHODS; CRYSTAL-STRUCTURES; CARBON-DIOXIDE; DRUG; OPTIMIZATION; NUCLEATION; PARAMETERS; EQUILIBRIA; SOLUTE;
D O I：
10.1016/j.molliq.2022.120481
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：
Tolfenamic acid (TFA) has been used until recently in prevention and treatment of diseases with the pain and inflammation symptoms. It also showed an inhibitory activity to the growth of cancer cells in pan-creas. However, use of TFA was ceased due to a number of side effects, and today it is not used in clinical practice. Conformational polymorphism of TFA makes it unique regarding possible modifications of its polymorphic forms, and till now new forms can be revealed. One of the methods of accessing different polymorphic modifications is applying supercritical fluidic techniques using the scCO2 medium. The present paper reports the analysis of the spatial structure and conformational preferences of TFA in DMSO d6 (at 25 degrees C and 0.1 MPa) and in a mixed solvent scCO2 + DMSO (45 degrees C and 9 MPa) based on nuclear Overhauser effect spectroscopy. The results demonstrate changes in the conformer fractions depending on the medium used and thermodynamic parameters of state, which provides important control means for obtaining new polymorphic modifications.(c) 2022 Elsevier B.V. All rights reserved.
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页数：10
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