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

来源：

ARCHIV DER PHARMAZIE | 2012年 / 345卷 / 05期

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

页码：386 / 392

页数：7

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
BARALDI, PG
SIMONI, D
MORODER, F
MANFREDINI, S
MUCCHI, L
VECCHIA, FD
ORSOLINI, P
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (03) : 557 - 560
[3] Proliferation, cell cycle and apoptosis in cancer
Evan, GI
Vousden, KH
[J]. 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
Hanahan, D
Weinberg, RA
[J]. CELL, 2000, 100 (01) : 57 - 70
[7] The inhibitors of apoptosis (IAPs) as cancer targets
Hunter, Allison M.
LaCasse, Eric C.
Korneluk, Robert G.
[J]. 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
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
[J]. 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
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
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) : 6299 - 6310

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