Visible Light Driven Coupling of 2-aminopyridines and α-Keto Vinyl Azides for the Synthesis of Imidazo[1,2-a]pyridines and Their Cytotoxicity

被引：16
作者：
Adiyala, Praveen Reddy [1 ]
Sastry, Kasinathuni Naga Visweswara [1 ,2 ]
Kovvuri, Jeshma [1 ]
Nagarajan, Apoorva [1 ]
Reddy, Velma Ganga [1 ]
Bin Sayeed, Ibrahim [1 ]
Nayak, Vedinthe Lakshma [1 ]
Maurya, Ram Awatar [3 ]
Kamal, Ahmed [1 ,2 ,4 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Med Chem & Biotechnol, Hyderabad 500007, Andhra Pradesh, India
[2] NIPER, Dept Med Chem, Hyderabad 500037, Andhra Pradesh, India
[3] North East Inst Sci & Technol, CSIR, Chem Sci & Technol Div, Appl Organ Chem Grp, Jorhat 785006, Assam, India
[4] King Saud Univ, Coll Sci, Dept Chem, Catalyt Chem Res Chair, Riyadh 11451, Saudi Arabia
来源：
CHEMISTRYSELECT | 2017年 / 2卷 / 26期
关键词：
Vinylazides; Imidazo[1,2-a]pyridine; Ru(bpy)(3)Cl-2 center dot 6H(2)O; 2H-azirine; FUSED BETA-CARBOLINES; PHOTOREDOX CATALYSIS; ANNULATION; CHEMISTRY; BATCH;
D O I：
10.1002/slct.201700952
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
alpha-Keto vinyl azides and 2-aminopyridines were coupled to yield 1-aryl-N-(2-arylimidazo[1,2-a]pyridin-3-yl)methanimines in the presence of visible light using Ru(bpy)(3)Cl-2 center dot 6H(2)O as a photocatalyst. This synthetic protocol allows the formation of 3 new C-N bonds in the overall transformation at ambient temperature. It is applicable to a wide range of vinyl azides and 2-aminopyridines providing a straightforward access to a variety of highly functionalized imidazo[1,2-a]pyridines in high yields. The synthesized imidazo[1,2-a]pyridines were evaluated for their cytotoxic activity against a set of four selected human cancer cell lines i.e, A549 (lung cancer), DU-145 (prostate cancer), MCF-7 (breast cancer) and Hela (cervical cancer). Many compounds of the series (4e, 4g, 4i, 4j and 4u) exhibited promising cytotoxicity in these cancer cell lines.
引用
收藏
页码：8158 / 8161
页数：4
相关论文
共 36 条
[1]   An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines [J].
Adib, Mehdi ;
Sheibani, Esmail ;
Zhu, Long-Guan ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2008, 49 (34) :5108-5110
[2]   Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines [J].
Adiyala, Praveen Reddy ;
Mani, Geeta Sai ;
Nanubolu, Jagadeesh Babu ;
Shekar, Kunta Chandra ;
Maurya, Ram Awatar .
ORGANIC LETTERS, 2015, 17 (17) :4308-4311
[3]   Synthesis of α-amino amidines through molecular iodine-catalyzed three-component coupling of isocyanides, aldehydes and amines [J].
Adiyala, Praveen Reddy ;
Chandrasekhar, D. ;
Kapure, Jeevak Sopanrao ;
Reddy, Chada Narsimha ;
Maurya, Ram Awatar .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :2065-2070
[4]   Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation [J].
Alfonsi, Kim ;
Colberg, Juan ;
Dunn, Peter J. ;
Fevig, Thomas ;
Jennings, Sandra ;
Johnson, Timothy A. ;
Kleine, H. Peter ;
Knight, Craig ;
Nagy, Mark A. ;
Perry, David A. ;
Stefaniak, Mark .
GREEN CHEMISTRY, 2008, 10 (01) :31-36
[5]  
Alibeik M. A., 2014, CATAL SCI TECHNOL, V4, P1151
[6]   Recent synthetic additions to the visible light photoredox catalysis toolbox [J].
Angnes, Ricardo A. ;
Li, Zhou ;
Correia, Carlos Roque D. ;
Hammond, Gerald B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (35) :9152-9167
[7]   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
[8]   Enantioselective Catalysis of Photochemical Reactions [J].
Brimioulle, Richard ;
Lenhart, Dominik ;
Maturi, Mark M. ;
Bach, Thorsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :3872-3890
[9]   Imidazo[1,2-α]pyridines.: Part 2:: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors [J].
Byth, KF ;
Culshaw, JD ;
Green, S ;
Oakes, SE ;
Thomas, AP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) :2245-2248
[10]   One-Pot Regiospecific Synthesis of Imidazo[1,2-a]pyridines: A Novel, Metal-Free, Three-Component Reaction for the Formation of C-N, C-O, and C-S Bonds [J].
Cao, Hua ;
Liu, Xiaohang ;
Zhao, Limin ;
Cen, Jinghe ;
Lin, Jingxin ;
Zhu, Qiuxia ;
Fu, Minling .
ORGANIC LETTERS, 2014, 16 (01) :146-149
1234