Structure and physicochemical characterization of a naproxen–picolinamide cocrystal

Kerr, Hannah E.; Softley, Lorna K.; Suresh, Kuthuru; Hodgkinson, Paul; Evans, Ivana Radosavljević

doi:10.1107/s2053229616011980

Cited by 32 publications

(31 citation statements)

References 45 publications

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“…It should be noted that for processes involving chiral systems the dependence on concentration is typical and is usually explained by the tendency of chiral compounds to form associates . It is known that naphthalene and its substituted derivatives, as well as NPX, form dimers and excimers in the solid state and in solution . In particular, the NPX–NPX dyad excimer is described herein .…”

Section: Introductionmentioning

confidence: 66%

“…Heterodimers (cocrystals) of NPX with different organic compounds and biomolecules (nicotinamide, isonicotinamide, picolinamide, alanine, tyrosine, tryptophan (Trp), etc.) have also been reported in the literature, and X‐ray and solid‐state NMR spectroscopy studies have shown that these associates are formed through hydrogen bonding of NPX carboxylic groups with NH and OH groups of the partner molecules …”

Section: Introductionmentioning

confidence: 95%

“…[17][18][19][20][21][22] It is knownt hat naphthalene and its substituted derivatives, as well as NPX, form dimers and excimers in the solid state and in solution. [23][24][25][26] In particular,t he NPX-NPX dyad excimer is described herein. [5] For naphthalene and its derivatives, dimerization occurs due to the interaction of aromatic rings.…”

Section: Introductionmentioning

confidence: 99%

“…have also been reported in the literature, and X-ray and solid-state NMR spectroscopy studies have shown that these associates are formed through hydrogen bonding of NPX carboxylic groups with NH and OH groups of the partnerm olecules. [26] Therefore, herein, X-ray and NMR spectroscopy methods are used to confirm the possibility of dyad dimer formation. Additionally,t he CIDNP enhancement coefficients for diastereomers observed in solutionw ith different ratios of diastereomer concentrationsw erec alculated, by taking into account the assumption that ET occurredi nt he dyad dimers.…”

Section: Introductionmentioning

confidence: 99%

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Spin Selectivity in Chiral Linked Systems

Ageeva

Khramtsova

Magin

et al. 2018

Chemistry A European J

105

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This work has shown spin selectivity in electron transfer (ET) of diastereomers of (R,S)-naproxen-(S)-N-methylpyrrolidine and (R,S)-naproxen-(S)-tryptophan dyads. Photoinduced ET in these dyads is interesting because of the still unexplained phenomenon of stereoselectivity in the drug activity of enantiomers. The chemically induced dynamic nuclear polarization (CIDNP) enhancement coefficients of (R,S)-diastereomers are double those of the (S,S)-analogue. These facts are also interesting because spin effects are among the most sensitive, even to small changes in spin and molecular dynamics of paramagnetic particles. Therefore, CIDNP reflects the difference in magnetoresonance parameters (hyperfine interaction constants (HFIs), g-factor difference) and lifetimes of the paramagnetic forms of (R,S)- and (S,S)-diastereomers. The difference in HFI values for diastereomers has been confirmed by a comparison of CIDNP experimental enhancement coefficients with those calculated. Additionally, the dependence of the CIDNP enhancement coefficients on diastereomer concentration has been observed for the naproxen-N-methylpyrrolidine dyad. This has been explained by the participation of ET in homo-(R,S-R,S or S,S-S,S) and hetero-(R,S-S,S) dimers of dyads. In this case, the effectivity of ET, and consequently, CIDNP, is supposed to be different for (R,S)- and (S,S)-homodimers, heterodimers, and monomers. The possibility of dyad dimer formation has been demonstrated by using high-resolution X-ray and NMR spectroscopy techniques.

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Section: Introductionmentioning

confidence: 66%

Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Spin Selectivity in Chiral Linked Systems

Ageeva

Khramtsova

Magin

et al. 2018

Chemistry A European J

105

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show abstract

“…There are reference data on the formation of dimers and excimers of substituted naphthalenes and NPX in solution . The association of NPX with biomolecules was also recorded by means of solid‐state NMR spectroscopy and XRD, and shown to occur due to the formation of hydrogen bonds between the carboxyl group of NPX and the NH and OH protons of biomolecules (amino acids and others) …”

Section: Relationship Between Spin Selectivity and Dyad Associationmentioning

confidence: 99%

Role of Association in Chiral Catalysis: From Asymmetric Synthesis to Spin Selectivity

Ageeva

Khramtsova

Magin

et al. 2018

Chemistry A European J

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The origin of biomolecules in the pre-biological period is still a matter of debate, as is the unclarified nature of the differences in enantiomer properties, especially for the medically important activity of chiral drugs. With regards to the first issue, significant progress was made in the last decade of the 20th century through experimental confirmation of Frank's popular theory on chiral catalysis in spontaneous asymmetric synthesis. Soai examined the chiral catalysis of the alkylation of achiral aldehydes by achiral reagents. Attempts to model this process demonstrated the key role of chiral compounds associates as templates for chiral synthesis. However, the elementary mechanism of alkylation and the role of free radicals in this process are still incompletely understood. Meanwhile, the influence of external magnetic fields on chiral enrichment in the radical path of alkylation has been predicted. In addition, the role of chiral dyad association in another radical process, electron transfer (ET), has been recently demonstrated by the following methods: chemically induced dynamic nuclear polarisation (CIDNP), NMR spectroscopy, XRD and photochemistry. The CIDNP analysis of ET in two dyads has revealed a phenomenon first observed for chiral systems, spin selectivity, which results in the difference between the CIDNP enhancement coefficients of dyad diastereomers. These dyads are linked systems consisting of the widespread drug (S)-naproxen (NPX) or its R analogue and electron donors, namely, (S)-tryptophan and (S)-N-methylpyrrolidine. Because NPX is one of the most striking examples of the difference in the therapeutic properties of enantiomers, the appearance of spin selectivity in dyads with (S)- and (R)-NPX and S donors can shed light on the chemical nature of these differences. This review is devoted to discussing the chemical nature of spin selectivity and the role of chiral associates in the chiral catalysis of an elementary radical reaction: ET in chiral dyads.

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A nano-cocrystal strategy to improve the dissolution rate and oral bioavailability of baicalein

Wang

et al. 2019

Asian Journal of Pharmaceutical Sciences

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Structure and physicochemical characterization of a naproxen–picolinamide cocrystal

Cited by 32 publications

References 45 publications

Spin Selectivity in Chiral Linked Systems

Spin Selectivity in Chiral Linked Systems

Role of Association in Chiral Catalysis: From Asymmetric Synthesis to Spin Selectivity

A nano-cocrystal strategy to improve the dissolution rate and oral bioavailability of baicalein

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