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Voloshin, Ya. Z.; Varzatskii, Оleg А.; Vorontsov, Ivan I.; Antipin, M. Yu.; Tkachenko, E. Yu.

doi:10.1023/a:1019617803429

Cited by 5 publications

(1 citation statement)

References 2 publications

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“…The angles H∙∙∙O=S are about 124–125°. It should be noted that according to the Cambridge Structural Database, similar intermolecular interactions between oximes and DMSO solvate molecules are observed in 22 solid-state structures [ 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 , 95 ] with the mean O-H∙∙∙O distance 1.816 Å and the shortest distances of 1.65–1.69 Å [ 88 , 89 ].…”

Section: Resultsmentioning

confidence: 98%

Experimental and Computational Investigation of the Oxime Bond Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime

et al. 2023

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11H-Indeno[1,2-b]quinoxalin-11-one oxime (IQ-1) and tryptanthrin-6-oxime are potent c-Jun N-terminal kinase 3 (JNK-3) inhibitors demonstrating neuroprotective, anti-inflammatory and anti-arthritic activity. However, the stereochemical configuration of the oxime carbon–nitrogen double bond (E- or Z-) in these compounds was so far unknown. In this contribution, we report the results of the determination of the double bond configuration in the solid state by single crystal X-ray diffraction and in solution by 1D and 2D NMR techniques and DFT calculations. It was found that both in the solid state and in solution, IQ-1 adopts the E-configuration stabilized by intermolecular hydrogen bonds, in contrast to previously assumed Z-configuration that could be stabilized only by an intramolecular hydrogen bond.

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Section: Resultsmentioning

confidence: 98%

Experimental and Computational Investigation of the Oxime Bond Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime

et al. 2023

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ChemInform Abstract: Potentially Hexadentate Bisazine Dioximate Ligands: “Correct” Synthetic Procedure and Encapsulation Reactions of the Iron(II) Ion.

et al. 2002

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ketone derivativesketone derivatives (acyclic compounds) P 0220 -069Potentially Hexadentate Bisazine Dioximate Ligands: "Correct" Synthetic Procedure and Encapsulation Reactions of the Iron(II) Ion.-Condensation of diacetyl monoxime hydrazone with glyoxal or 1,2-diketones affords potentially hexadentate bisazine dioximes like (I). Reaction of the products with Fe 2+ ions does not lead to the expected trinuclear clathrochelates but to the dinuclear clathrochelates studied previously. -(VOLOSHIN, YA. Z.; VARZATSKII, O. A.; VORONTSOV, I. I.; ANTIPIN, M. YU.; TKACHENKO, E. YU.; Russ.

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2002

Clathrochelates

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Untitled

Cited by 5 publications

References 2 publications

Experimental and Computational Investigation of the Oxime Bond Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime

Experimental and Computational Investigation of the Oxime Bond Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime

ChemInform Abstract: Potentially Hexadentate Bisazine Dioximate Ligands: “Correct” Synthetic Procedure and Encapsulation Reactions of the Iron(II) Ion.

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