PASE Pseudo‐Four‐Component Synthesis and Docking Studies of New 5‐C‐Substituted 2, 4‐Diamino‐5H‐Chromeno[2, 3‐b]pyridine‐3‐Carbonitriles. Issue 17 (13th June 2017)

• Record Type: Journal Article
• Authors: Vereshchagin, Anatoly N.; Elinson, Michail N.; Anisina, Yuliya E.; Ryzhkov, Fedor V.; Novikov, Roman A.; Egorov, Mikhail P.
• Is Part Of: ChemistrySelect. Volume 2:Issue 17(2017)
• Page Start: 4593
• Page End: 4597
• Publication Date: 2017-06-13
• Subjects: chromeno[2, 3-b]pyridines -- 1, 3-cyclohexanediones -- docking studies -- malononitrile -- multicomponent reactions; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201700606
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A pot, atom and step economy (PASE) synthesis of new 5‐C substituted 2, 4‐diamino‐5 H ‐chromeno[2, 3‐ b ]pyridine‐3‐carbonitriles was carried out. This process involves the one‐pot, pseudo four‐component reaction of salicylaldehydes, malononitrile, 1, 3‐cyclohexanediones and Et3 N as a catalyst in acetonitrile at reflux. This novel one‐pot reaction provides an effective and convenient way to 5‐C cyclohexyl‐functionalized chromeno[2, 3‐ b ]pyridines, which are promising compounds for different biomedical applications. The procedure utilizes readily available reagents, it is easily carried out and the work up is not complicated. 2, 4‐diamino‐5‐(2‐hydroxy‐6‐oxocyclohex‐1‐en‐1‐yl)‐5 H ‐chromeno[2, 3‐ b ]pyridine‐3‐carbonitriles are crystallized directly from the reaction mixture and the isolation includes only filtration. Molecular docking studies of the synthesized 2, 4‐diamino‐5 H ‐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). Abstract : A pot, atom and step economy (PASE) synthesis of new 5‐C substituted 2, 4‐diamino‐5 H ‐chromeno[2, 3‐ b ]pyridine‐3‐carbonitriles was carried out. This process involves the one‐pot, pseudo‐four‐component reaction of salicylaldehydes, malononitrile, 1, 3‐cyclohexanediones and Et3 N as a catalyst in acetonitrile at reflux. Docking studies of compounds obtained revealed remarkable potential activity against MK‐1 and MK‐2, which competitive with known inhibitor.