Regioselective synthesis and molecular docking studies of functionalized imidazo [1,2-a]pyridine derivatives through MCRs

被引:4
作者
Yadav, Maruti B. [1 ]
Singh, Pooja [2 ]
Jeong, Yeon Tae [1 ]
机构
[1] Pukyong Natl Univ, Dept Image Sci & Engn, Pusan 608737, South Korea
[2] Gyeongsang Natl Univ GNU, Plant Mol Biol & Biotechnol Res Ctr PMBBRC, Div Appl Life Sci, 501 Jinju daero, Jinju 52828, South Korea
关键词
Imidazo[1; 2-a]pyrimidine; Knoevenagel condensation; Michael adduct; Regioselectivity; Molecular docking; ONE-POT; 3-COMPONENT REACTION; ANNULATED PYRIDINES; INHIBITORS; PYRAZINES; ACCESS; CYCLIZATION; BINDING; TARGET; ARYL;
D O I
10.1007/s11030-023-10669-9
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A efficient protocol has been developed for the synthesis of regioselective imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine derivatives through cascade reaction between 2-aminopyridine, arylelglyoxal, and 4-hydroxypyran via three-component reaction to prepare targeted compounds with good to excellent yields. The advantages of this transformation are a catalyst-free reaction, green solvent, operationally simple, scalable, and eco-friendly. The product collects with simple filtration which avoided tedious and expensive purification techniques. In addition, computational studies like molecular docking were conducted to provide the theoretical possibilities of binding these types of synthesized compounds to the VEGFR2 receptors as potential key inhibitors of tumor cell growth and angiogenesis.
引用
收藏
页码:171 / 182
页数:12
相关论文
共 61 条
[1]   The benzodiazepine binding site of GABAA receptors as a target for the development of novel anxiolytics [J].
Atack, JR .
EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2005, 14 (05) :601-618
[2]   A Novel Solvent-Free Approach to Imidazole Containing Nitrogen-Bridgehead Heterocycles [J].
Attanasi, Orazio A. ;
Bianchi, Luca ;
Campisi, Linda A. ;
De Crescentini, Lucia ;
Favi, Gianfranco ;
Mantellini, Fabio .
ORGANIC LETTERS, 2013, 15 (14) :3646-3649
[3]   BENZIMIDAZOLE CONDENSED RING-SYSTEM .9. POTENTIAL ANTINEOPLASTICS - NEW SYNTHESIS OF SOME PYRIDO[1,2-A]BENZIMIDAZOLES AND RELATED DERIVATIVES [J].
BADAWEY, E ;
KAPPE, T .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (04) :327-332
[4]   Synthesis of imidazo[1,2-a]pyridines: a decade update [J].
Bagdi, Avik Kumar ;
Santra, Sougata ;
Monir, Kamarul ;
Hajra, Alakananda .
CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575
[5]   Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale [J].
Bagdi, Avik Kumar ;
Rahman, Matiur ;
Santra, Sougata ;
Majee, Adinath ;
Hajra, Alakananda .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) :1741-1747
[6]  
Biovia D.S., 2017, RELEASE
[7]   Parallel synthesis of 3-aminoimidazo[1,2-a]pyridines and pyrazines by a new three-component condensation [J].
Blackburn, C ;
Guan, B ;
Fleming, P ;
Shiosaki, K ;
Tsai, S .
TETRAHEDRON LETTERS, 1998, 39 (22) :3635-3638
[8]   A three-component solid-phase synthesis of 3-aminoimidazo[1,2-a]azines [J].
Blackburn, C .
TETRAHEDRON LETTERS, 1998, 39 (31) :5469-5472
[9]  
Boerner RJ, 1997, PSYCHOPHARMAKOTHERAP, V4, P145
[10]   Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines [J].
Cai, Zhong-Jian ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) :2686-2692