Design, synthesis, and mechanism of action of 2-(3-hydroxy-5-methoxyphenyl)-6-pyrrolidinylquinolin-4-one as a potent anticancer lead

被引：9

作者：

Cheng, Yung-Yi ^{[1
]}

Liu, Chin-Yu ^{[1
]}

Tsai, Meng-Tung ^{[1
]}

Lin, Hui-Yi ^{[1
]}

Yang, Jai-Sing ^{[2
]}

Wu, Tian-Shung ^{[3
]}

Kuo, Sheng-Chu ^{[1
,4
]}

Huang, Li-Jiau ^{[1
]}

Lee, Kuo-Hsiung ^{[4
,5
]}

机构：

[1] China Med Univ, Grad Inst Pharmaceut Chem, Taichung 40402, Taiwan

[2] China Med Univ, Dept Pharmacol, Taichung 40402, Taiwan

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

[4] China Med Univ Hosp, Chinese Med Res & Dev Ctr, Taichung 40447, Taiwan

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 18期

关键词：

2-(Hydroxyphenyl)quinolin-4-one derivatives; Antiproliferative activity; Anticancer lead development; Prodrug; ANTITUMOR AGENTS; TUBULIN POLYMERIZATION; BIOLOGICAL EVALUATION; ANTIMITOTIC AGENTS; IN-VIVO; QUINOLONE; 2-PHENYL-4-QUINOLONES; CYTOTOXICITY; DERIVATIVES; INHIBITION;

D O I：

10.1016/j.bmcl.2013.06.083

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

New 6- (or 6,7-) substituted 2-(hydroxyl substituted phenyl)quinolin-4-one derivatives were synthesized and screened for antiproliferative effects against cancer cell lines. Structure-activity relationship correlations were established and the most promising compound 2-(3-hydroxy-5-methoxyphenyl)-6-pyrrolidin-1-ylquinolin-4-one (6h) exhibited strong inhibitory activity against various human cancer cell lines, particularly non-small cell lung cancer NCI-H522. Additional studies suggested a mechanism of action resembling that of the antimitotic drug vincristine. The presence of a C-ring OH group in 6h will allow this compound to be converted readily to a water soluble and physicochemically stable hydrophilic prodrug. Compound 6h is proposed as a new anticancer lead compound. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5223 / 5227

页数：5

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