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

• Published in: Journal of molecular structure 2017-10, Vol.1146, p.766-772
• Main Authors: Vereshchagin, Anatoly N., Elinson, Michail N., Anisina, Yuliya E., Ryzhkov, Fedor V., Goloveshkin, Alexander S., Novikov, Roman A., Egorov, Mikhail P.
• Format: Article
• Language: English
• Subjects: chromeno[2,3-b]pyridines; Keto-enol equilibrium; Molecular docking studies; Multicomponent reactions; Powder XRD; Spectroscopic studies
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.06.044

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, 1H, 13C 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. [Display omitted] •Multicomponent synthesis of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles was carried out.•The compounds obtained were characterized by elemental analysis, IR, XRD, mass, 1H, 13C and NOESY spectral studies.•The chromeno[2,3-b]pyridines obtained are enols in solid phase.•Keto-enol equilibrium is observed in DMSO-d6 solutions.•Chlorine-containing chromeno[2,3-b]pyridines have best binding energy both MK-1 and MK-2.