Chinese Journal of Organic Chemistry >
Synthesis, Anticancer and Antibacterial Activities of Novel 2-Amino-4-phenylthiazole Derivatives Containing Amide Moiety
Received date: 2017-04-13
Revised date: 2017-04-23
Online published: 2017-05-04
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
Zhang Zhihu , Chen Yu , Chai Baoshan , Yang Xiaoman , Cai Xiaoyu , Cui Bo , You Song . Synthesis, Anticancer and Antibacterial Activities of Novel 2-Amino-4-phenylthiazole Derivatives Containing Amide Moiety[J]. Chinese Journal of Organic Chemistry, 2017 , 37(9) : 2377 -2384 . DOI: 10.6023/cjoc201704023
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