Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

被引：33

作者：

Chen, Chien-Ting ^{[1
]}

Hsu, Mei-Hua ^{[1
]}

Cheng, Yung-Yi ^{[1
]}

Liu, Chin-Yu ^{[1
]}

Chou, Li-Chen ^{[1
]}

Huang, Li-Jiau ^{[1
]}

Wu, Tian-Shung ^{[2
,3
]}

Yang, Xiaoming ^{[4
]}

Lee, Kuo-Hsiung ^{[2
,4
]}

Kuo, Sheng-Chu ^{[1
,2
]}

机构：

[1] China Med Univ, Grad Inst Pharmaceut Chem, North Sect, Taichung, Taiwan

[2] China Med Univ Hosp, Chinese Med Res & Dev Ctr, Taichung, Taiwan

[3] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan

[4] Univ N Carolina, UNC Eshelman Sch Pharm, Nat Prod Res Labs, Chapel Hill, NC 27599 USA

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2011年 / 46卷 / 12期

关键词：

Selenophene; Melanoma; Structure-activity relationships (SAR); Anticancer activity; Quinolin-4-one analogs; POTENT ANTITUMOR AGENTS; TUBULIN POLYMERIZATION; BIOLOGICAL EVALUATION; CATALYZED AMIDATION; ANTIMITOTIC AGENTS; CYTOTOXICITY; INHIBITION; 2-PHENYL-4-QUINOLONES; 2-ARYL-4-QUINOLONES; DERIVATIVES;

D O I：

10.1016/j.ejmech.2011.10.017

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.

引用

页码：6046 / 6056

页数：11

共 30 条

[1]

[Anonymous], 2005, NAME REACTIONS HETER

[2]

Camps R. B. D., 1899, CHEM BER, V32, P3228

[3] Design and Synthesis of 2-(3-Benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly [J].

Chang, Yu-Hsun ;

Hsu, Mei-Hua ;

Wang, Sheng-Hung ;

Huang, Li-Jiau ;

Qian, Keduo ;

Morris-Natschke, Susan L. ;

Hamel, Ernest ;

Kuo, Sheng-Chu ;

Lee, Kuo-Hsiung .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (15) :4883-4891

[4] Anticancer mechanisms of YC-1 in human lung cancer cell line, NCI-H226 [J].

Chen, Chun-Jen ;

Hsu, Mei-Hua ;

Huang, Li-Jiau ;

Yamori, Takao ;

Chung, Fing-Gung ;

Lee, Fang-Yu ;

Teng, Che-Ming ;

Kuo, Sheng-Chu .

BIOCHEMICAL PHARMACOLOGY, 2008, 75 (02) :360-368

[5] Antitumor agents .178. Synthesis and biological evaluation of substituted 2-aryl-1,8-naphthyridin-4(1H)-ones as antitumor agents that inhibit tubulin polymerization [J].

Chen, K ;

Kuo, SC ;

Hsieh, MC ;

Mauger, A ;

Lin, CM ;

Hamel, E ;

Lee, KH .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (19) :3049-3056

[6] Antitumor agents .174. 2',3',4',5,6,7-substituted 2-phenyl-1,8-naphthyridin-4-ones: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization [J].

Chen, K ;

Kuo, SC ;

Hsieh, MC ;

Mauger, A ;

Lin, CM ;

Hamel, E ;

Lee, KH .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (14) :2266-2275

[7] Design, Synthesis, and Preclinical Evaluation of New 5,6- (or 6,7-) Disubstituted-2-(fluorophenyl)quinolin-4-one Derivatives as Potent Antitumor Agents [J].

Chou, Li-Chen ;

Tsai, Meng-Tung ;

Hsu, Mei-Hua ;

Wang, Sheng-Hung ;

Way, Tzong-Der ;

Huang, Chi-Hung ;

Lin, Hui-Yi ;

Qian, Keduo ;

Dong, Yizhou ;

Lee, Kuo-Hsiung ;

Huang, Li-Jiau ;

Kuo, Sheng-Chu .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (22) :8047-8058

[8] Synthesis and Preclinical Evaluations of 2-(2-Fluorophenyl)-6,7-methylenedioxyquinolin-4-one Monosodium Phosphate (CHM-1-P-Na) as a Potent Antitumor Agent [J].

Chou, Li-Chen ;

Chen, Chien-Ting ;

Lee, Jang-Chang ;

Way, Tzong-Der ;

Huang, Chi-Hung ;

Huang, Shih-Ming ;

Teng, Che-Ming ;

Yamori, Takao ;

Wu, Tian-Shung ;

Sun, Chung-Ming ;

Chien, Du-Shieng ;

Qian, Keduo ;

Morris-Natschke, Susan L. ;

Lee, Kuo-Hsiung ;

Huang, Li-Jiau ;

Kuo, Sheng-Chu .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (04) :1616-1626

[9] Microwave-assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated 2′-aminoacetophenones [J].

Ding, Derong ;

Li, Xin ;

Wang, Xin ;

Du, Yongli ;

Shen, Jingkang .

TETRAHEDRON LETTERS, 2006, 47 (39) :6997-6999

[10] Synthesis, structure, and antiproliferative activity of selenophenfurin, an inosine 5'-monophosphate dehydrogenase inhibitor analogue of selenazofurin [J].

Franchetti, P ;

Cappellacci, L ;

AbuSheikha, G ;

Jayaram, HN ;

Gurudutt, VV ;

Sint, T ;

Schneider, BP ;

Jones, WD ;

Goldstein, BM ;

Perra, G ;

DeMontis, A ;

Loi, AG ;

LaColla, P ;

Grifantini, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (11) :1731-1737

← 1 2 3 →