Autor: |
Potapov, Vladislava V. Matveevskaya, Dmitry I. Pavlov, Anastasia R. Kovrizhina, Taisiya S. Sukhikh, Evgeniy H. Sadykov, Pavel V. Dorovatovskii, Vladimir A. Lazarenko, Andrei I. Khlebnikov, Andrei S. |
Jazyk: |
angličtina |
Rok vydání: |
2023 |
Předmět: |
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Zdroj: |
Pharmaceutics; Volume 15; Issue 7; Pages: 1802 |
ISSN: |
1999-4923 |
DOI: |
10.3390/pharmaceutics15071802 |
Popis: |
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. |
Databáze: |
OpenAIRE |
Externí odkaz: |
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