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

doi:10.6023/cjoc201704023

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

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含酰胺结构的新型2-氨基-4-苯基噻唑类化合物的合成及抗癌和抗菌活性研究

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

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 E-mail:yousong206@aliyun.com

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

Zhang Zhihu^a,b, Chen Yu^a, Chai Baoshan^c, Yang Xiaoman^d, Cai Xiaoyu^d, Cui Bo^d, You Song^a

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 E-mail:yousong206@aliyun.com

1. Synthesis, Anticancer and Antibacterial Activities of Novel 2-Amino-4-phenylthiazole Derivatives Containing Amide Moiety.PDF(1365KB)

Abstract

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

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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]. Chin. J. Org. Chem., 2017, 37(9): 2377-2384.

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含酰胺结构的新型2-氨基-4-苯基噻唑类化合物的合成及抗癌和抗菌活性研究

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

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