期刊
PHARMACEUTICS
卷 15, 期 7, 页码 -出版社
MDPI
DOI: 10.3390/pharmaceutics15071802
关键词
kinase inhibitor; oxime; crystal structure; nuclear magnetic resonance; rotation barrier
The stereochemical configuration of the oxime carbon-nitrogen double bond in IQ-1 and tryptanthrin-6-oxime compounds was determined as the E-configuration using single crystal X-ray diffraction, 1D and 2D NMR techniques, and DFT calculations. This finding contradicts the previous assumption of a Z-configuration and demonstrates the stability of the E-configuration through intermolecular hydrogen bonds.
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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