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

被引：32
|
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
收藏
页码：6046 / 6056
页数：11
相关论文
共 50 条
  • [1] Design, synthesis, and mechanism of action of 2-(3-hydroxy-5-methoxyphenyl)-6-pyrrolidinylquinolin-4-one as a potent anticancer lead
    Cheng, Yung-Yi
    Liu, Chin-Yu
    Tsai, Meng-Tung
    Lin, Hui-Yi
    Yang, Jai-Sing
    Wu, Tian-Shung
    Kuo, Sheng-Chu
    Huang, Li-Jiau
    Lee, Kuo-Hsiung
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (18) : 5223 - 5227
  • [2] Design, Synthesis, and Preclinical Evaluation of New 5,6- (or 6,7-) Disubstituted-2-(fluorophenyl)quinolin-4-one Derivatives as Potent Antitumor Agents
    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
  • [3] Synthesis and Preclinical Evaluations of 2-(2-Fluorophenyl)-6,7-methylenedioxyquinolin-4-one Monosodium Phosphate (CHM-1-P-Na) as a Potent Antitumor Agent
    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
  • [4] Design and synthesis of 6,7-methylenedioxy-4-substituted phenylquinolin-2(1H)-one derivatives as novel anticancer agents that induce apoptosis with cell cycle arrest at G2/M phase
    Chen, Yi-Fong
    Lin, Yi-Chien
    Huang, Po-Kai
    Chan, Hsu-Chin
    Kuo, Sheng-Chu
    Lee, Kuo-Hsiung
    Huang, Li-Jiau
    BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (17) : 5064 - 5075
  • [5] 6,7-Dimethoxy-2-methyl-4-substituted quinazolines: Design, synthesis, EGFR inhibitory activity, in vitro cytotoxicity, and in silico studies
    Saleh, Nermin S.
    El-Sayed, Nahed N. E.
    Saleh, Ola A.
    Allam, Heba Abdelrasheed
    Mohamed, Nada M.
    Abbas, Safinaz E. -S.
    Said, Mona F.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2025, 290
  • [6] Design and Synthesis of 2-(3-Benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly
    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
  • [7] Synthesis and In Vitro Anticancer Activity of 6-Ferrocenylpyrimidin-4(3H)-one Derivatives
    Grabovskiy, Stanislav A.
    Muhammadiev, Rinat S.
    Valiullin, Lenar R.
    Raginov, Ivan S.
    Kabal'nova, Natalie N.
    CURRENT ORGANIC SYNTHESIS, 2019, 16 (01) : 160 - 164
  • [8] Synthesis and in vitro and in vivo anticancer activity of novel 3-methyl-5H-isoxazolo[5′,4′:5,6]pyrido[2,3-b]indoles
    Rajanarendar, E.
    Reddy, K. Govardhan
    Ramakrishna, S.
    Reddy, M. Nagi
    Shireesha, B.
    Durgaiah, G.
    Reddy, Y. N.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (21) : 6677 - 6680
  • [9] An Efficient Synthesis of 1,2,4-triazine-6-one Derivatives and Their in vitro Anticancer Activity
    Zein, Mohamed Abd El-Latif
    El-Shenawy, Ahmed Ibrahim
    International Journal of Pharmacology, 2016, 12 (03) : 188 - 194
  • [10] Synthesis of 2-(6-substituted quinolin-4-yl)-1-alkoxypropan-2-ol as potential antimycobacterial agents
    Shinde, Abhijit
    Thakare, Prashant P.
    Nandurkar, Yogesh
    Chavan, Abhijit
    Shaikh, Abdul Latif N.
    Mhaske, Pravin C.
    CHEMICAL PAPERS, 2023, 77 (07) : 3791 - 3802
12345