Synthesis, structural, spectroscopic and docking studies of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles

被引：33

作者：

Vereshchagin, Anatoly N. ^{[1
]}

Elinson, Michail N. ^{[1
]}

Anisina, Yuliya E. ^{[1
]}

Ryzhkov, Fedor V. ^{[1
]}

Goloveshkin, Alexander S. ^{[2
]}

Novikov, Roman A. ^{[1
]}

Egorov, Mikhail P. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia

[2] AN Nesmeyanov Inst Organoelement Cpds, Vavilova Str 28, Moscow 119991, Russia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2017年 / 1146卷

关键词：

chromeno[2,3-b]pyridines; Multicomponent reactions; Spectroscopic studies; Powder XRD; Keto-enol equilibrium; Molecular docking studies; NAD(+)-DEPENDENT DNA-LIGASE; SCAFFOLD; MALONONITRILE; INHIBITION; MOLECULES; EFFICIENT; DESIGN; POTENT;

D O I：

10.1016/j.molstruc.2017.06.044

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Multicomponent synthesis of 5-C substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles from salicylaldehydes 2-aminoprop-1-ene-1,1,3-tricarbonitrile and 1,3-cyclohexanediones was carried out in 59-88% yields. The structures of compounds obtained were characterized by several techniques, including elemental analysis, IR, XRD, mass, H-1, C-13 and NOESY spectral studies. The chromeno[2,3-b] pyridines obtained are enols in solid phase. Keto-enol equilibrium is observed in DMSO solutions. Molecular docking studies of the synthesized chromeno[2,3-b]pyridine-3-carbonitriles were also carried out to elucidate their relationship with the binding pockets of the mitogen activated protein kinase (MK). It have been found that chlorine-containing chromeno[2,3-b]pyridines have best binding energy both MK 1 and MK-2. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：766 / 772

页数：7

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