Synthesis, in vitro anticancer activity and SAR studies of arylated imidazo[1,2-a]pyrazine-coumarin hybrids

被引:41
作者
Goel, Richa [1 ]
Luxami, Vijay [1 ]
Paul, Kamaldeep [1 ]
机构
[1] Thapar Univ, Sch Chem & Biochem, Patiala 147001, Punjab, India
关键词
NATIONAL-CANCER-INSTITUTE; DRUG DISCOVERY; DESIGN; DERIVATIVES; INHIBITORS; KINASE; PYRAZINES; POTENT;
D O I
10.1039/c5ra00584a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new series of imidazo[1,2-a]pyrazine-coumarin hybrids have been synthesized by the combination of two biologically active moieties, imidazo[1,2-a]pyrazine and coumarin, followed by the Suzuki-Miyaura cross coupling reaction for monoarylation at the C6 position and symmetrical/unsymmetrical diarylation at the C3 and C6 positions. These compounds were further screened for their in vitro antitumor activities.
引用
收藏
页码:37887 / 37895
页数:9
相关论文
共 27 条
[1]   N-Fused Imidazoles As Novel Anticancer Agents That Inhibit Catalytic Activity of Topoisomerase IIα and Induce Apoptosis in G1/S Phase [J].
Baviskar, Ashish T. ;
Madaan, Chetna ;
Preet, Ranjan ;
Mohapatra, Purusottam ;
Jain, Vaibhav ;
Agarwal, Amit ;
Guchhait, Sankar K. ;
Kundu, Chanakya N. ;
Banerjee, Uttam C. ;
Bharatam, Prasad V. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (14) :5013-5030
[2]   Structure-based design of imidazo[1,2-a] pyrazine derivatives as selective inhibitors of Aurora-A kinase in cells [J].
Bouloc, Nathalie ;
Large, Jonathan M. ;
Kosmopoulou, Magda ;
Sun, Chongbo ;
Faisal, Amir ;
Matteucci, Mizio ;
Reynisson, Johannes ;
Brown, Nathan ;
Atrash, Butrus ;
Blagg, Julian ;
McDonald, Edward ;
Linardopoulos, Spiros ;
Bayliss, Richard ;
Bavetsias, Vassilios .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (20) :5988-5993
[3]   SOME PRACTICAL CONSIDERATIONS AND APPLICATIONS OF THE NATIONAL-CANCER-INSTITUTE IN-VITRO ANTICANCER DRUG DISCOVERY SCREEN [J].
BOYD, MR ;
PAULI, KD .
DRUG DEVELOPMENT RESEARCH, 1995, 34 (02) :91-109
[4]   HETEROCYCLES .167. TELE-SUBSTITUTION AND OTHER TRANSFORMATIONS OF IMIDAZO[1,2-A]-AND S-TRIAZOLO[4,3-A]PYRAZINES [J].
BRADAC, J ;
FUREK, Z ;
JANEZIC, D ;
MOLAN, S ;
SMERKOLJ, I ;
STANOVNIK, B ;
TISLER, M ;
VERCEK, B .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (26) :4197-4201
[5]   Protonation Equilibria and Lipophilicity of Sarafloxacin [J].
Caco, Ana I. ;
Tome, Liliana C. ;
Dohrn, Ralf ;
Marrucho, Isabel M. .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2010, 55 (09) :3160-3163
[6]   Antitumor agents 292. Design, synthesis and pharmacological study of S- and O-substituted 7-mercapto- or hydroxy-coumarins and chromones as potent cytotoxic agents [J].
Chen, Ying ;
Liu, Hong-Rui ;
Liu, Hong-Shan ;
Cheng, Ming ;
Xia, Peng ;
Qian, Keduo ;
Wu, Pei-Chi ;
Lai, Chin-Yu ;
Xia, Yi ;
Yang, Zheng-Yu ;
Morris-Natschke, Susan L. ;
Lee, Kuo-Hsiung .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 49 :74-85
[7]   New diarylureas and diarylamides containing 1,3,4-triarylpyrazole scaffold: Synthesis, antiproliferative evaluation against melanoma cell lines, ERK kinase inhibition, and molecular docking studies [J].
Choi, Won-Kyoung ;
El-Gamal, Mohammed I. ;
Choi, Hong Seok ;
Baek, Daejin ;
Oh, Chang-Hyun .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) :5754-5762
[8]   Discovery of GS-9973, a Selective and Orally Efficacious Inhibitor of Spleen Tyrosine Kinase [J].
Currie, Kevin S. ;
Kropf, Jeffrey E. ;
Lee, Tony ;
Blomgren, Peter ;
Xu, Jianjun ;
Zhao, Zhongdong ;
Gallion, Steve ;
Whitney, J. Andrew ;
Maclin, Deborah ;
Lansdon, Eric B. ;
Maciejewski, Patricia ;
Rossi, Ann Marie ;
Rong, Hong ;
Macaluso, Jennifer ;
Barbosa, James ;
Di Paolo, Julie A. ;
Mitchell, Scott A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (09) :3856-3873
[9]  
Czarnik AW, 1996, ACCOUNTS CHEM RES, V29, P112, DOI 10.1021/ar950256n
[10]   Versatile templates for the development of novel kinase inhibitors: Discovery of novel CDK inhibitors [J].
Dwyer, Michael P. ;
Paruch, Kamil ;
Alvarez, Carmen ;
Doll, Ronald J. ;
Keertikar, Kerry ;
Duca, Jose ;
Fischmann, Thierry O. ;
Hruza, Alan ;
Madison, Vincent ;
Lees, Emma ;
Parry, David ;
Seghezzi, Wolfgang ;
Sgambellone, Nicole ;
Shanahan, Frances ;
Wiswell, Derek ;
Guzi, Timothy J. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (22) :6216-6219