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
| Parent link: | Pharmaceutics.— .— Basel: MDPI AG Vol. 15, iss. 7.— 2023.— Article number 1802, 20 p. |
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| Other Authors: | , , , , , , , , |
| Summary: | Title screen 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 Текстовый файл |
| Published: |
2023
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| Subjects: | |
| Online Access: | https://doi.org/10.3390/pharmaceutics15071802 |
| Format: | Electronic Book Chapter |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=682051 |
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| 200 | 1 | |a 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 |f Vladislava V. Matveevskaya, Dmitry I. Pavlov, Anastasia R. Kovrizhina [et al.] | |
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| 330 | |a 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 | ||
| 336 | |a Текстовый файл | ||
| 461 | 1 | |t Pharmaceutics |c Basel |n MDPI AG | |
| 463 | 1 | |t Vol. 15, iss. 7 |v Article number 1802, 20 p. |d 2023 | |
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a труды учёных ТПУ | |
| 610 | 1 | |a kinase inhibitor | |
| 610 | 1 | |a oxime | |
| 610 | 1 | |a crystal structure | |
| 610 | 1 | |a nuclear magnetic resonance | |
| 610 | 1 | |a rotation barrier | |
| 701 | 1 | |a Matveevskaya |b V. V. |g Vladislava Vadimovna | |
| 701 | 1 | |a Pavlov |b D. I. |g Dmitry Igorevich | |
| 701 | 1 | |a Kovrizhina |b A. R. |c biotechnology specialist |c Research Engineer of Tomsk Polytechnic University |f 1995- |g Anastasia Ruslanovna |9 22266 | |
| 701 | 1 | |a Sukhikh |b T. S, |g Taisiya Sergeevna | |
| 701 | 1 | |a Sadykov |b E. Kh. |g Evgeny Khasanovich | |
| 701 | 1 | |a Dorovatovskii |b P. V. |g Pavel Vladimirovich | |
| 701 | 1 | |a Lazarenko |b V. A. |g Vladimir Aleksandrovich | |
| 701 | 1 | |a Khlebnikov |b A. I. |c Chemist |c Professor of Tomsk Polytechnic University |f 1963- |g Andrey Ivanovich |9 17500 | |
| 701 | 1 | |a Potapov |b A. S. |g Andrey Sergeevich | |
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