2-Amino-3-cyano-4-(5-arylisoxazol-3-yl)-4H-chromenes: Synthesis and In Vitro Cytotoxic Activity

被引:51
作者
Akbarzadeh, Tahmineh [1 ,2 ]
Rafinejad, Ali [1 ,2 ]
Mollaghasem, Javad Malekian [1 ,2 ]
Safavi, Maliheh [1 ,2 ,3 ]
Fallah-Tafti, Asal [1 ,2 ]
Pordeli, Mahboobeh [3 ]
Ardestani, Sussan Kabudanian [3 ]
Shafiee, Abbas [1 ,2 ]
Foroumadi, Alireza [1 ,2 ]
机构
[1] Univ Tehran Med Sci, Drug Design & Dev Res Ctr, Tehran, Iran
[2] Univ Tehran Med Sci, Fac Pharm, Dept Med Chem, Tehran, Iran
[3] Univ Tehran, Inst Biochem & Biophys, Dept Biochem, Tehran, Iran
关键词
4-(5-Arylisoxazol-3-yl)-4H-chromenes; Cancer; Cytotoxic activity; Synthesis; THROUGHPUT SCREENING ASSAY; APOPTOSIS INDUCERS; SERIES; DISCOVERY; 4-ARYL-4H-CHROMENES; PROLIFERATION;
D O I
10.1002/ardp.201100345
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new series of 4-aryl-4H-chromenes bearing a 5-arylisoxazol-3-yl moiety at the C-4 position were prepared as potential anticancer agents. The in vitro cytotoxic activity of the synthesized compounds was investigated against a panel of tumor cell lines including MCF-7 (breast cancer), KB (nasopharyngeal epidermoid carcinoma), Hep-G2 (liver carcinoma), MDA-MB-231 (breast cancer), and SKNMC (human neuroblastoma) using the MTT colorimetric assay. Doxorubicin, a well-known anticancer drug, was used as positive standard drug. Among the synthesized compounds, the 5-(3-methylphenyl)isoxazol-3-yl analog (7j) showed the most potent cytotoxic activity against all five human tumor cell lines.
引用
收藏
页码:386 / 392
页数:7
相关论文
共 17 条
[1]  
[Anonymous], CA CANC J CLIN, DOI DOI 10.3322/CAAC.20107
[2]   SYNTHESIS OF 2-(5'-SUBSTITUTED ISOXAZOL-3'-YL)-4-OXO-3-THIAZOLIDINYLALKANOIC ACIDS [J].
BARALDI, PG ;
SIMONI, D ;
MORODER, F ;
MANFREDINI, S ;
MUCCHI, L ;
VECCHIA, FD ;
ORSOLINI, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (03) :557-560
[3]   Proliferation, cell cycle and apoptosis in cancer [J].
Evan, GI ;
Vousden, KH .
NATURE, 2001, 411 (6835) :342-348
[4]  
Foroumadi A, 2007, ASIAN J CHEM, V19, P1391
[5]  
Gourdeau H, 2004, MOL CANCER THER, V3, P1375
[6]   The hallmarks of cancer [J].
Hanahan, D ;
Weinberg, RA .
CELL, 2000, 100 (01) :57-70
[7]   The inhibitors of apoptosis (IAPs) as cancer targets [J].
Hunter, Allison M. ;
LaCasse, Eric C. ;
Korneluk, Robert G. .
APOPTOSIS, 2007, 12 (09) :1543-1568
[8]  
Kasibhatla S, 2004, MOL CANCER THER, V3, P1365
[9]   Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay.: 2.: Structure-activity relationships of the 7- and 5-, 6-, 8-positions [J].
Kemnitzer, W ;
Kasibhatla, S ;
Jiang, SC ;
Zhang, H ;
Zhao, JH ;
Jia, SJ ;
Xu, LF ;
Crogan-Grundy, C ;
Denis, R ;
Barriault, N ;
Vaillancourt, L ;
Charron, S ;
Dodd, J ;
Attardo, G ;
Labrecque, D ;
Lamothe, S ;
Gourdeau, H ;
Tseng, B ;
Drewe, J ;
Cai, SX .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (21) :4745-4751
[10]   Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay.: 1.: Structure-activity relationships of the 4-aryl group [J].
Kemnitzer, W ;
Drewe, J ;
Jiang, SC ;
Zhang, H ;
Wang, Y ;
Zhao, JH ;
Jia, SJ ;
Herich, J ;
Labreque, D ;
Storer, R ;
Meerovitch, K ;
Bouffard, D ;
Rej, R ;
Denis, R ;
Blais, C ;
Lamothe, S ;
Attardo, G ;
Gourdeau, H ;
Tseng, B ;
Kasibhatla, S ;
Cai, SX .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) :6299-6310