Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2377-2384.DOI: 10.6023/cjoc201704023 Previous Articles     Next Articles



张志华a,b, 陈羽a, 柴宝山c, 杨小漫d, 蔡晓瑜d, 崔博d, 游松a   

  1. a 沈阳药科大学生命科学与生物制药学院 沈阳 110016;
    b 辽宁工业大学化学与环境工程学院 锦州 121001;
    c 沈阳化工研究院生物与医药研究所 沈阳 110021;
    d 锦州医科大学药学院 锦州 121000
  • 收稿日期:2017-04-13 修回日期:2017-04-23 发布日期:2017-05-04
  • 通讯作者: 游松

Synthesis, Anticancer and Antibacterial Activities of Novel 2-Amino-4-phenylthiazole Derivatives Containing Amide Moiety

Zhang Zhihua,b, Chen Yua, Chai Baoshanc, Yang Xiaomand, Cai Xiaoyud, Cui Bod, You Songa   

  1. a School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang 110016;
    b School of Chemical and Environmental Engineering, Liaoning University of Technology, Jinzhou 121001;
    c Biotechnology and Pharmaceutical Research Laboratory, Shenyang Research Institute of Chemical Industry Ltd., Shenyang 110021;
    d College of Pharmacy, Jinzhou Medical University, Jinzhou 121000
  • Received:2017-04-13 Revised:2017-04-23 Published:2017-05-04
  • Contact: 10.6023/cjoc201704023

A series of novel 2-amino-4-phenylthiazole derivatives containing amide moiety were designed and synthesized based on the structural features of sorafenib. The structures of synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS. Both the anticancer and antibacterial activities of all the target compounds were evaluated. Most of the compounds showed potent activities, especially N-(3-(2-acetamidothiazol-4-yl)phenyl)-3-fluorobenzamide (4n) exhibited a remarkable antitumor effect against human colon cancer cell line (HT29) and human lung epithelial cells (A549) cells with IC50 values of 6.31 and 7.98 μmol·L-1, respectively. Further mechanistic study revealed that 4n can influence the Raf/MEK/ERK pathway. In addition, N-(3-(2-acetamidothiazol-4-yl)phenyl)-3,4-dichlorobenzamide (4h), N-(3-(2-acetamidothiazol-4-yl)phenyl)-3-chlorobenzamide (4i) and N-(3-(2-acetamidothiazol-4-yl)phenyl)-2,4-dichlorobenzamide (4o) exhibit moderate antibacterial activity against the tested bacteria.

Key words: thiazole derivative, amide, synthesis, anticancer, antibacterial