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

Belov, Konstantin V.; Dyshin, A. A.; Krest’yaninov, М. А.; Ефимов, С. В.; Khodov, Ilya A.; Киселев, М. Г.

doi:10.1016/j.molliq.2022.120481

Cited by 18 publications

(15 citation statements)

References 55 publications

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“…This technique can be used to determine the interproton distances of small molecules. For further details, refer to the provided references [ 69 , 70 , 71 , 72 , 73 , 74 ].

…”

Section: Resultsmentioning

confidence: 99%

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Exploring the Conformational Equilibrium of Mefenamic Acid Released from Silica Aerogels via NMR Analysis

Khodov

Sobornova

Mulloyarova

et al. 2023

IJMS

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This study examines the influence of mefenamic acid on the physical and chemical properties of silica aerogels, as well as its effect on the sorption characteristics of the composite material. Solid state magic angle spinning nuclear magnetic resonance (MAS NMR) and high-pressure 13C NMR kinetic studies were conducted to identify the presence of mefenamic acid and measure the kinetic rates of CO2 sorption. Additionally, a high-pressure T1–T2 relaxation-relaxation correlation spectroscopy (RRCOSY) study was conducted to estimate the relative amount of mefenamic acid in the aerogel’s pores, and a high-pressure nuclear Overhauser effect spectoscopy (NOESY) study was conducted to investigate the conformational preference of mefenamic acid released from the aerogel. The results indicate that mefenamic acid is affected by the chemical environment of the aerogel, altering the ratio of mefenamic acid conformers from 75% to 25% in its absence to 22% to 78% in the presence of aerogel.

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“…This technique can be used to determine the interproton distances of small molecules. For further details, refer to the provided references [ 69 , 70 , 71 , 72 , 73 , 74 ].

…”

Section: Resultsmentioning

confidence: 99%

“…An approach based on the spectroscopy of the nuclear Overhauser effect, developed in our previous works [ 69 , 70 , 73 ], was used to solve this problem. Experiments at supercritical parameters of the state of the solvent (CO 2 ) were conducted using the unique scientific installation “Fluid-spectrum” of the G.A.…”

Section: Methodsmentioning

confidence: 99%

Exploring the Conformational Equilibrium of Mefenamic Acid Released from Silica Aerogels via NMR Analysis

Khodov

Sobornova

Mulloyarova

et al. 2023

IJMS

View full text Add to dashboard Cite

show abstract

“…High-pressure NMR cell ( Figure 2 b pos. 4) [ 36 , 37 , 38 ] is a single crystal sapphire tube of high-pressure production (Daedalus Innovations, Aston, Pennsylvania, USA). The small size of the ampoule, which has an inner diameter of 3 mm, an outer diameter of 5 mm and a total length of 87 mm, allows it to work at pressures up to 30 MPa.…”

Section: Methodsmentioning

confidence: 99%

Molecular Dynamics and Nuclear Magnetic Resonance Studies of Supercritical CO2 Sorption in Poly(Methyl Methacrylate)

et al. 2022

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The study of supercritical carbon dioxide sorption processes is an important and urgent task in the field of “green” chemistry and for the selection of conditions for new polymer material formation. However, at the moment, the research of these processes is very limited, and it is necessary to select the methodology for each polymer material separately. In this paper, the principal possibility to study the powder sorption processes using 13C nuclear magnetic resonance spectroscopy, relaxation-relaxation correlation spectroscopy and molecular dynamic modeling methods will be demonstrated based on the example of polymethylmethacrylate and supercritical carbon dioxide. It was found that in the first nanoseconds and seconds during the sorption process, most of the carbon dioxide, about 75%, is sorbed into polymethylmethacrylate, while on the clock scale the remaining 25% is sorbed. The methodology presented in this paper makes it possible to select optimal conditions for technological processes associated with the production of new polymer materials based on supercritical fluids.

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“…Therefore, it is necessary to develop approaches capable of preliminary estimating of the producing probability of a desired API form on early stages of the mechanochemical synthesis. Nuclear Overhauser effect spectroscopy (NOESY) was shown to be an efficient method of finding small molecules conformers in solutions [ 11 , 17 , 18 , 19 , 20 , 21 ] and in fluids [ 22 , 23 , 24 , 25 ], in the case of conformation-dependent polymorphism of drug compounds, which is the factor defining the obtained solid phase. This approach can be effective, both for understanding the processes occurring in the pre-nucleation state and for predicting the probability of obtaining certain polymorphic forms.…”

Section: Introductionmentioning

confidence: 99%

Conformational Screening of Arbidol Solvates: Investigation via 2D NOESY

et al. 2023

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Understanding of the nucleation process’s fundamental principles in saturated solutions is an urgent task. To do this task, it is necessary to control the formation of polymorphic forms of biologically active compounds. In certain cases, a compound can exist in a single polymorphic form, but have several solvates which can appear in different crystal forms, depending on the medium and conditions of formation, and show different pharmaceutical activity. In the present paper, we report on the analysis of Arbidol conformational preferences in two solvents of different polarities—deuterated chloroform and dimethyl sulfoxide—at 25 °C, using the 2D NOESY method. The Arbidol molecule has various solvate forms depending on the molecular conformation. The method based on the nuclear Overhauser effect spectroscopy was shown to be efficient in the analysis of complex heterocyclic compounds possessing conformation-dependent pseudo-polymorphism. It is one of the types of polymorphism observed in compounds forming crystal solvates. Combined use of NMR methods and X-ray data allowed determining of conformer populations of Arbidol in CDCl3 and DMSO-d6 which were found to be 8/92% and 37/63%, respectively. The preferred conformation in solution is the same that appears in stable crystal solvates of Arbidol.

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

Cited by 18 publications

References 55 publications

Exploring the Conformational Equilibrium of Mefenamic Acid Released from Silica Aerogels via NMR Analysis

Exploring the Conformational Equilibrium of Mefenamic Acid Released from Silica Aerogels via NMR Analysis

Molecular Dynamics and Nuclear Magnetic Resonance Studies of Supercritical CO2 Sorption in Poly(Methyl Methacrylate)

Conformational Screening of Arbidol Solvates: Investigation via 2D NOESY

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