Novel 5-(benzyloxy)pyridin-2(1H)-one derivatives as potent c-Met inhibitors

被引：7
|
作者：
Zhang, Dengyou [1 ]
Ai, Jing [2 ]
Liang, Zhongjie [3 ]
Zhu, Wei [1 ]
Peng, Xia [2 ]
Chen, Xianjie [1 ]
Ji, YinChun [2 ]
Jiang, Hualiang [1 ,4 ]
Luo, Cheng [1 ]
Geng, Meiyu [2 ]
Liu, Hong [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, State Key Lab Drug Res,CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Div Antitumor Pharmacol, Shanghai 201203, Peoples R China
[3] Soochow Univ, Ctr Syst Biol, Suzhou 215006, Jiangsu, Peoples R China
[4] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 08期
基金：
中国国家自然科学基金;
关键词：
c-Met; EBC-1; cell; Tyrosine kinase receptor; KINASE INHIBITORS; DISCOVERY;
D O I：
10.1016/j.bmcl.2013.02.037
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of novel 5-(benzyloxy)pyridin-2(1H)-ones were designed, synthesized and biologically evaluated for c-Met inhibition. Various amides and benzoimidazoles at C-3 position were investigated. A potent compound 12b with a c-Met IC50 of 12 nM was identified. This compound exhibited potent inhibition of EBC-1 cell associated with c-Met constitutive activation and showed high selectivity for c-Met than other tested 11 kinases. The binding model 12b with c-Met was disclosed by docking analysis. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2408 / 2413
页数：6
相关论文
共 50 条
  • [41] Design and synthesis of benzofuro[3,2-b]pyridin-2(1H)-one derivatives as anti-leukemia agents by inhibiting Btk and PI3Kδ
    Liu, Linyi
    Shi, Bingyu
    Li, Xinyu
    Wang, Xiangqian
    Lu, Xiang
    Cai, Xuerong
    Huang, Ali
    Luo, Guoshun
    You, Qidong
    Xiang, Hua
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (15) : 4537 - 4543
  • [42] Discovery of novel 7-azaindole derivatives bearing dihydropyridazine moiety as c-Met kinase inhibitors
    Tang, Qidong
    Wang, Linxiao
    Duan, Yongli
    Wang, Wenhui
    Huang, Shunmin
    Zhi, Jia
    Jia, Shuang
    Zhu, Wufu
    Wang, Ping
    Luo, Rong
    Zheng, Pengwu
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 133 : 97 - 106
  • [43] Phenanthrotriazine Derivatives Containing Arylidine Hydrazone Moieties as Novel Potential c-Met Inhibitors with Anticancer Effect
    Edraki, Najmeh
    Jamei, Mohammad Hasan
    Haghighijoo, Zahra
    Kayani, Zahra
    Raufi, Elaheh
    Eskandari, Masoomeh
    Firouzi, Maryam
    Sadeghpour, Hossein
    Miri, Ramin
    Khoshneviszadeh, Mehdi
    Firuzi, Omidreza
    IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH, 2021, 20 (03): : 516 - 531
  • [44] Design, synthesis, and biological evaluation of thieno[2,3-d]pyrimidine derivatives as novel dual c-Met and VEGFR-2 kinase inhibitors
    Li, Jieming
    Gu, Weijie
    Bi, Xinzhou
    Li, Huilan
    Liao, Chen
    Liu, Chunxia
    Huang, Wenlong
    Qian, Hai
    BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (24) : 6674 - 6679
  • [45] Expeditious one-pot synthesis of C3-piperazinyl-substituted quinolines: key precursors to potent c-Met inhibitors
    Wang, Yuanxiang
    Ai, Jing
    Liu, Gang
    Geng, Meiyu
    Zhang, Ao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (17) : 5930 - 5933
  • [46] Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety as c-Met kinase inhibitors
    Tang, Qidong
    Wang, Linxiao
    Tu, Yayi
    Zhu, Wufu
    Luo, Rong
    Tu, Qidong
    Wang, Ping
    Wu, Chunjiang
    Gong, Ping
    Zheng, Pengwu
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (07) : 1680 - 1684
  • [47] Design, synthesis and biological evaluation of 1H-pyrrolo[2,3-b]pyridine and 1H-pyrazolo[3,4-b]pyridine derivatives as c-Met inhibitors
    Liu, Na
    Wang, Yanfen
    Huang, Gongchao
    Ji, Conghui
    Fan, Wei
    Li, Haitao
    Cheng, Ying
    Tian, Hongqi
    BIOORGANIC CHEMISTRY, 2016, 65 : 146 - 158
  • [48] Design, Synthesis, and Biological Evaluation of Pyridineamide Derivatives Containing a 1,2,3-Triazole Fragment as Type II c-Met Inhibitors
    Xiong, Hehua
    Cheng, Jianxin
    Zhang, Jianqing
    Zhang, Qian
    Xiao, Zhen
    Zhang, Han
    Tang, Qidong
    Zheng, Pengwu
    MOLECULES, 2020, 25 (01):
  • [49] Multicomponent cascade reaction of 3-formylchromones: Highly regioselective synthesis of functionalized pyridin-2(1H)-ones
    Yun, Xinghan
    Chen, Li
    Lv, Ying
    Lu, Zihan
    Huang, Kun
    Yan, Shengjiao
    GREEN SYNTHESIS AND CATALYSIS, 2023, 4 (03): : 231 - 239
  • [50] One step synthesis of 1,5-diaryl pyridin-2(1H)-ones from 2-aryl vinamidinium salts and N-aryl cyanoacetamides
    Yang, Jiabin
    Su, Guoqiang
    Ren, Yu
    Chen, Yang
    TETRAHEDRON, 2014, 70 (45) : 8642 - 8647
12345