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

Bibliographic Details
Parent link:Pharmaceutics.— .— Basel: MDPI AG
Vol. 15, iss. 7.— 2023.— Article number 1802, 20 p.
Other Authors: Matveevskaya V. V. Vladislava Vadimovna, Pavlov D. I. Dmitry Igorevich, Kovrizhina A. R. Anastasia Ruslanovna, Sukhikh T. S, Taisiya Sergeevna, Sadykov E. Kh. Evgeny Khasanovich, Dorovatovskii P. V. Pavel Vladimirovich, Lazarenko V. A. Vladimir Aleksandrovich, Khlebnikov A. I. Andrey Ivanovich, Potapov A. S. Andrey Sergeevich
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
Subjects:
электронный ресурс
труды учёных ТПУ
kinase inhibitor
oxime
crystal structure
nuclear magnetic resonance
rotation barrier
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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