Design and synthesis of new 2-arylnaphthyridin-4-ones as potent antitumor agents targeting tumorigenic cell lines
Liu, Chin-Yu1; Cheng, Yung-Yi1; Chang, Ling-Chu1; Huang, Li-Jiau1; Chou, Li-Chen1,2; Huang, Chi-Hung2; Tsai, Meng-Tung1; Liao, Chih-Chang1; Hsu, Mei-Hua1; Lin, Hui-Yi1; Wu, Tian-Shung3; Wen, Yen-Fang4; Zhao, Yu5,6; Kuo, Sheng-Chu1,6; Lee, Kuo-Hsiung6,7; Kuo,SC (reprint author),China Med Univ,Grad Inst Pharmaceut Chem,91 Hsueh Shih Rd,Taichung 40402,Taiwan.; sckuo@mail.cmu.edu.tw; khlee@unc.edu
2015-01-27
Source PublicationEUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume90Pages:775-787
AbstractTo develop new anticancer drug candidates from 2-arylnaphthyridin-4-one (AN), we have designed and synthesized a series of 3'-hydroxy and 6-hydroxy derivatives of AN. The results of cytotoxicity screening indicated that the replacement of the 3'-methoxy moiety on the C-ring phenyl group of AN (6a-e) with 3'-hydroxy (7a-e) made no significant effect on the inhibitory activity against HL-60, Hep3B and NCI-H460 cancer cell lines. On the other hand, replacing the 6-methoxy group on the A-ring of AN (6g-i) with a 6-hydroxy group (7g-i) resulted in reduced inhibitory activity against the above three cancer cell lines. Among the above-mentioned target compounds, 2-(3-hydroxyphenyl)-5-methyl-1,8-naphthyridin-4(1H)-one (7a) demonstrated the greatest potency and the best selectivity toward tumorigenic cancer cell lines. In a 7a preliminary mechanism of action study in Hep3B hepatoma cells, 7a showed the effects on microtubules followed by cell cycle arrest and sequentially led to apoptosis.
Keyword2-arylnaphthyridin-4-ones Antitumor Agents Phosphate Prodrug
Subject AreaChemistry, Medicinal
DOI10.1016/j.ejmech.2014.11.062
Indexed BySCI ; IC
Language英语
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal
WOS IDWOS:000348951900061
Citation statistics
Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/20665
Collection中国科学院东亚植物多样性与生物地理学重点实验室
Corresponding AuthorKuo,SC (reprint author),China Med Univ,Grad Inst Pharmaceut Chem,91 Hsueh Shih Rd,Taichung 40402,Taiwan.; sckuo@mail.cmu.edu.tw; khlee@unc.edu
Affiliation1.China Med Univ, Grad Inst Pharmaceut Chem, Taichung 40402, Taiwan
2.Hung Kuang Univ, Grad Sch Biotechnol, Taichung 43302, Taiwan
3.Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan
4.Ind Technol Res Inst, Hsinchu 31040, Taiwan
5.Chinese Acad Sci, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China
6.Univ N Carolina, UNC Eshelman Sch Pharm, Nat Prod Res Labs, Chapel Hill, NC 27599 USA
7.China Med Univ & Hosp, Chinese Med Res & Dev Ctr, Taichung 40447, Taiwan
Recommended Citation
GB/T 7714
Liu, Chin-Yu,Cheng, Yung-Yi,Chang, Ling-Chu,et al. Design and synthesis of new 2-arylnaphthyridin-4-ones as potent antitumor agents targeting tumorigenic cell lines[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2015,90:775-787.
APA Liu, Chin-Yu.,Cheng, Yung-Yi.,Chang, Ling-Chu.,Huang, Li-Jiau.,Chou, Li-Chen.,...&khlee@unc.edu.(2015).Design and synthesis of new 2-arylnaphthyridin-4-ones as potent antitumor agents targeting tumorigenic cell lines.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,90,775-787.
MLA Liu, Chin-Yu,et al."Design and synthesis of new 2-arylnaphthyridin-4-ones as potent antitumor agents targeting tumorigenic cell lines".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 90(2015):775-787.
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