Synthesis and pharmacological properties of a new 3-hydroxypyridine derivative

Yasnetsov, V. V.; Skachilova, S. Ya.; Сернов, Л. Н.; Воронина, Т. А.

doi:10.1007/s11094-012-0760-x

Cited by 7 publications

(9 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The IR spectra of the monoclinic (M) and orthorhombic (O) polymorphs of (I) were practically identical and in good agreement with the previously reported spectrum of the salt (Yasnetsov et al, 2010). The intensive bands at 1543-1547 and 1647-1650 cm À1 present in these spectra were assigned to vibration of the COO À group of the anion and the wag-stretch vibration of the cation, respectively.…”

Section: Resultssupporting

confidence: 88%

“…The original synthetic procedure reported by Yasnetsov et al (2010Yasnetsov et al ( , 2012 was modified in order to increase the yield of crystalline product.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

“…The crystal structures of two succinic acid derivatives of 2-ethyl-3-hydroxy-6-methylpyridine have been reported (Lyakhov et al, 2012). Recently, in a search for new analogs of Mexidol, Yasnetsov et al (2010) obtained a new compound, namely 2-ethyl-3-hydroxy-6-methylpyridinium hydrogen N-acetyl-l-glutamate, (I). It has been established that (I) exhibits antihypoxic activity on various models of acute hypoxia (hypoxia is a pathological condition in which the body, or a part of the body, is deprived of an adequate oxygen supply) in mice and produces an equal or larger effect than Mexidol (Yasnetsov et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

“…Recently, in a search for new analogs of Mexidol, Yasnetsov et al (2010) obtained a new compound, namely 2-ethyl-3-hydroxy-6-methylpyridinium hydrogen N-acetyl-l-glutamate, (I). It has been established that (I) exhibits antihypoxic activity on various models of acute hypoxia (hypoxia is a pathological condition in which the body, or a part of the body, is deprived of an adequate oxygen supply) in mice and produces an equal or larger effect than Mexidol (Yasnetsov et al, 2012). We report here the crystal structures of monoclinic (M) and orthorhombic (O) polymorphs of (I) obtained from different solvent systems and determined from laboratory powder diffraction data.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Two polymorphs of 2-ethyl-3-hydroxy-6-methylpyridinium hydrogenN-acetyl-L-glutamate from powder diffraction data

Чернышев

Efimov²,

Paseshnichenko

et al. 2013

Acta Crystallogr C

View full text Add to dashboard Cite

The title salt, C8H12NO(+)·C7H10NO5(-), crystallizes in two polymorphic modifications, viz. monoclinic (M) and orthorhombic (O). The crystal structures of both polymorphic modifications have been established from laboratory powder diffraction data. The crystal packing motifs in the two polymorphs are different, but the conformations of the anions are generally similar. In M, the anions are linked by pairs of hydrogen bonds of the N-H···O and O-H···O types into chains along the b-axis direction, and neighbouring molecules within the chain are related by the 21 screw axis. The cations link these chains via O-H···O and N-H···O hydrogen bonds into layers parallel to (001). In O, the anions are linked by O-H···O hydrogen bonds into helices along [001], and neighbouring molecules within the helix are related by the 21 screw axis. The neighbouring helical turns are linked by N-H···O hydrogen bonds. The cations link the helices via O-H···O and N-H···O hydrogen bonds, thus forming a three-dimensional network.

show abstract

Section: Resultssupporting

confidence: 88%

“…The original synthetic procedure reported by Yasnetsov et al (2010Yasnetsov et al ( , 2012 was modified in order to increase the yield of crystalline product.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Two polymorphs of 2-ethyl-3-hydroxy-6-methylpyridinium hydrogenN-acetyl-L-glutamate from powder diffraction data

Чернышев

Efimov²,

Paseshnichenko

et al. 2013

Acta Crystallogr C

View full text Add to dashboard Cite

show abstract

“…Mexidol is currently more popular as it is less toxic than Emoxipine (Levitskaya et al, 2016). A recently discovered salt of emoxypine with N-acetylglutamic acid was shown to improve biological action in rats (Yasnetsov et al, 2010(Yasnetsov et al, , 2012. The crystal structures of known EMX salts show that emoxypine is able to form polymorphic salt forms (Chernyshev et al, 2013), as well as salts with different API/counter-ion ratios (API is an active pharmaceutical ingredient) (Lyakhov et al, 2012b).…”

Section: Introductionmentioning

confidence: 99%

Pharmaceutical salts of emoxypine with dicarboxylic acids

Manin

Voronin

Drozd

et al. 2018

Acta Crystallogr C Struct Chem

View full text Add to dashboard Cite

New salt forms of the antioxidant drug emoxypine (EMX, 2-ethyl-6-methylpyridin-3-ol) with pharmaceutically acceptable maleic (Mlt), malonic (Mln) and adipic (Adp) acids were obtained {emoxypinium maleate, CHNO·CHO, [EMX+Mlt], emoxypinium malonate, CHNO·CHO, [EMX+Mln], and emoxypinium adipate, CHNO·CHO, [EMX+Adp]} and their crystal structures determined. The molecular packing in the three EMX salts was studied by means of solid-state density functional theory (DFT), followed by QTAIMC (quantum theory of atoms in molecules and crystals) analysis. It was found that the major contribution to the packing energy comes from pyridine-carboxylate and hydroxy-carboxylate heterosynthons forming infinite one-dimensional ribbons, with [EMX+Adp] additionally stabilized by hydrogen-bonded C(9) chains of Adp ions. The melting processes of the [EMX+Mlt] (1:1), [EMX+Mln] (1:1) and [EMX+Adp] (1:1) salts were studied and the fusion enthalpy was found to increase with the increase of the calculated lattice energy. The dissolution process of the EMX salts in buffer (pH 7.4) was also studied. It was found that the formation of binary crystals of EMX with dicarboxylic acids increases the EMX solubility by more than 30 times compared to its pure form.

show abstract