Synthesis of cinnolines via Rh(III)-catalysed dehydrogenative C-H/N-H functionalization: aggregation induced emission and cell imaging

被引:65
作者
Mayakrishnan, Sivakalai [1 ]
Arun, Yuvaraj [1 ]
Balachandran, Chandrasekar [2 ]
Emi, Nobuhiko [2 ]
Muralidharan, Doraiswamy [1 ]
Perumal, Paramasivan Thirumalai [1 ]
机构
[1] Council Sci & Ind Res CSIR CLRI, Organ & Bioorgan Chem, Madras 600020, Tamil Nadu, India
[2] Fujita Hlth Univ, Dept Hematol, Toyoake, Aichi 4701192, Japan
关键词
SOLID-STATE FLUORESCENCE; BOND ACTIVATION; ALKYNES; ELECTROLUMINESCENCE; SEMICONDUCTORS; DERIVATIVES; LUMINOGENS; EMITTERS; OLEFINS; INDOLE;
D O I
10.1039/c5ob02045j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium catalysed dehydrogenative C-H/N-H functionalization was developed to construct phthalazino[2,3-a]-/indazolo[1,2-a]cinnolines by reacting N-phenyl phthalazine/indazole with alkynes. The synthesized compounds exhibit prominent fluorescence properties in solid and aggregation states. Their application in cell imaging was investigated using various cancer cell lines.
引用
收藏
页码:1958 / 1968
页数:11
相关论文
共 53 条
[21]   A molecular fluorescent dye for specific staining and imaging of RNA in live cells: a novel ligand integration from classical thiazole orange and styryl compounds [J].
Lu, Yu-Jing ;
Deng, Qiang ;
Hu, Dong-Ping ;
Wang, Zheng-Ya ;
Huang, Bao-Hua ;
Du, Zhi-Yun ;
Fang, Yan-Xiong ;
Wong, Wing-Leung ;
Zhang, Kun ;
Chow, Cheuk-Fai .
CHEMICAL COMMUNICATIONS, 2015, 51 (83) :15241-15244
[22]   Addressing species specific metabolism and solubility issues in a quinoline series of oral PDE4 inhibitors [J].
Lunniss, C. ;
Eldred, C. ;
Aston, N. ;
Craven, A. ;
Gohil, K. ;
Judkins, B. ;
Keeling, S. ;
Ranshaw, L. ;
Robinson, E. ;
Shipley, T. ;
Trivedi, N. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) :137-140
[23]   Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole [J].
Luo, JD ;
Xie, ZL ;
Lam, JWY ;
Cheng, L ;
Chen, HY ;
Qiu, CF ;
Kwok, HS ;
Zhan, XW ;
Liu, YQ ;
Zhu, DB ;
Tang, BZ .
CHEMICAL COMMUNICATIONS, 2001, (18) :1740-1741
[24]   Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions [J].
Lyons, Thomas W. ;
Sanford, Melanie S. .
CHEMICAL REVIEWS, 2010, 110 (02) :1147-1169
[25]   Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging [J].
Miao, Jianzhuang ;
Cui, Huaqing ;
Jin, Jing ;
Lai, Fangfang ;
Wen, Hui ;
Zhang, Xiang ;
Ruda, Gian Filippo ;
Chen, Xiaoguang ;
Yin, Dali .
CHEMICAL COMMUNICATIONS, 2015, 51 (05) :881-884
[26]   Switching of Polymorph-Dependent ESIPT Luminescence of an Imidazo[1,2-a]pyridine Derivative [J].
Mutai, Toshiki ;
Tomoda, Haruhiko ;
Ohkawa, Tatsuya ;
Yabe, Yuji ;
Araki, Koji .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (49) :9522-9524
[27]   Tetrasubstituted Olefinic Xanthene Dyes: Synthesis via Pd-Catalyzed 6-exo-dig Cyclization/C-H Activation of 2-Bromobenzyl-N-propargylamines and Solid State Fluorescence Properties [J].
Nandakumar, Avanashiappan ;
Perumal, Paramasivan Thirumalai .
ORGANIC LETTERS, 2013, 15 (02) :382-385
[28]   Synthesis of tetra-substituted olefins via annulation by Pd-catalyzed carbopalladation/C-H activation and solid state fluorescence properties [J].
Naveen, Kanagaraj ;
Nandakumar, Avanashiappan ;
Perumal, Paramasivan Thirumalai .
RSC ADVANCES, 2015, 5 (91) :74438-74446
[29]   Synthesis of Tetrasubstituted Olefins by Palladium-Catalyzed Double Heck Cyclization of Bromoenynes [J].
Naveen, Kanagaraj ;
Muralidharan, Doraiswamy ;
Perumal, Paramasivan Thirumalai .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (06) :1172-1176
[30]  
Patureau FW, 2012, ALDRICHIM ACTA, V45, P31