Insights into the crystal structure of two newly synthesized quinoxalines derivatives as potent inhibitor for c-Jun N-terminal kinases

doi:10.1080/07391102.2020.1844049

中山醫學大學機構典藏 CSMUIR > 中山醫學大學研究成果 > 期刊論文 > Item 310902500/24834

Please use this identifier to cite or link to this item: https://ir.csmu.edu.tw:8080/ir/handle/310902500/24834

Title:	Insights into the crystal structure of two newly synthesized quinoxalines derivatives as potent inhibitor for c-Jun N-terminal kinases
Authors:	Abad, N;El Bakri, Y;Lai, CH;Karthikeyan, S;Ramli, Y;Ferfra, S;Mague, JT;Essassi, E
Keywords:	Quinoxaline;crystal structure;Hirshfeld surface analysis;molecular docking;molecular dynamics
Date:	2022
Issue Date:	2022-08-09T08:08:45Z (UTC)
Publisher:	TAYLOR & FRANCIS INC
ISSN:	0739-1102
Abstract:	Two new compounds namely, ethyl (2E)-3-(dimethylamino)-2-(3-methoxyquinoxalin-2-yl)propen-2-enoate (II) and ethyl 2-(3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydroquinoxalin-2-yl)-3-phenylpropanoate (III) have been synthesized from ethyl 2-(oxo-3,4-dihydroquinoxalin-2-yl) acetate (I). The compounds were characterized using NMR (H-1 and C-13), Fourier transform infrared and confirmed by single crystal X-ray diffraction studies. The quinoxaline portion of II is almost planar with the substituent containing the dimethylamino and carboxyethyl groups rotated well out of its mean plane. In the crystal, C-H center dot center dot center dot O and C-H center dot center dot center dot N hydrogen bonds as well as C-H center dot center dot center dot pi(ring) interactions form chains having a U-shaped cross-section and running along the c-axis direction. Two sets of pair-wise C-H center dot center dot center dot O hydrogen bonds connect the chains into corrugated sheets. In III, the three substituents on the dihydroquinoxaline moiety are rotated well out of its mean plane. Three sets of C-H center dot center dot center dot O hydrogen bonds as well as C-H center dot center dot center dot pi(ring) and pi-pi-stacking interactions form layers approximately parallel to [001]. These are associated along the c-axis direction by additional C-H center dot center dot center dot pi(ring) interactions. Additionally, the Hirshfeld surface analyses showed that the H center dot center dot center dot H contact is the most important interaction for both II and III. In addition to this, molecular docking and dynamics studies were carried for these two compounds with the c-Jun N-terminal kinases (JNK1) molecule. Communicated by Ramaswamy H. Sarma
URI:	http://dx.doi.org/10.1080/07391102.2020.1844049 https://www.webofscience.com/wos/woscc/full-record/WOS:000589860500001 https://ir.csmu.edu.tw:8080/handle/310902500/24834
Relation:	JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS ,2022 ,v40 ,issue 6 ,p2797-2814
Appears in Collections:	[中山醫學大學研究成果] 期刊論文

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