Citation: 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 shu

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

Corresponding author: You Song, yousong206@aliyun.com
Received Date: 13 April 2017
Revised Date: 23 April 2017
Available Online: 4 September 2017

Figures(4)

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.
- thiazole derivative,
- amide,
- synthesis,
- anticancer,
- antibacterial
1. [1]
  (a) Heidorn, S. J.; Milagre, C.; Whittaker, S.; Nourry, A.; Niculescuduvas, I.; Dhomen, N.; Hussain, J.; Reisfilho, J. S.; Springer, C. J.; Pritchard, C. Cell 2010, 140, 209.
  (b) Hatzivassiliou, G.; Song, K.; Yen, I.; Brandhuber, B. J.; Anderson, D. J.; Alvarado, R.; Ludlam, M. J.; Stokoe, D.; Gloor, S. L.; Vigers, G. Nature 2010, 464, 431.
2. [2]
  Eisen, T.; Ahmad, T.; Flaherty, K. T.; Gore, M.; Kaye, S.; Marais, R.; Gibbens, I.; Hackett, S.; James, M.; Schuchter, L. M. Br. J. Cancer 2006, 95, 581. doi: 10.1038/sj.bjc.6603291
3. [3]
  (a) Wood, L. S. Community Oncol. 2006, 3, 558.
  (b) Chu, E. Y. ; Wanat, K. A. ; Miller, C. J. ; Amaravadi, R. K. ; Fecher, L. A. ; Brose, M. S. ; McGettigan, S. ; Giles, L. R. ; Schuchter, L. M. ; Seykora, J. T. J. Am. Acad. Dermatol. 2012, 67, 1265.
  (c) Autier, J. ; Escudier, B. ; Wechsler, J. ; Spatz, A. ; Robert, C. Arch. Dermatol. 2008, 144, 886.
4. [4]
  (a) Wu, C.; Wang, M.; Tang, Q.; Luo, R.; Chen, L.; Zheng, P.; Zhu, W. Molecules 2015, 20, 19361.
  (b) Yao, J.; Chen, J.; He, Z.; Sun, W.; Xu, W. Bioorg. Med. Chem. 2012, 20, 2923.
  (c) Jung, M. H.; El-Gamal, M. I.; Abdel-Maksoud, M. S.; Sim, T.; Yoo, K. H.; Oh, C.-H. Bioorg. Med. Chem. Lett. 2012, 22, 4362.
  (d) Jiao, Y.; Xin, B. T.; Zhang, Y.; Wu, J.; Lu, X.; Zheng, Y.; Tang, W.; Zhou, X. Eur. J. Med. Chem. 2015, 90, 170.
  (e) Kong, X.; Yao, Z.; He, Z.; Xu, W.; Yao, J. MedChemComm 2015, 6, 867.
  (f) Daydé-Cazals, B.; Fauvel, B.; Singer, M.; Feneyrolles, C.; Bestgen, B.; Gassiot, F.; Spenlinhauer, A.; Warnault, P.; Van Hijfte, N.; Borjini, N.; Chevé, G.; Yasri, A. J. Med. Chem. 2016, 59, 3886.
  (g) Yao, J.; He, Z.; Chen, J.; Chen, D.; Sun, W.; Xu, W. Chin. J. Chem. 2012, 30, 2423.
5. [5]
  (a) Gao, G. R.; Li, M. Y.; Lv, Y. C.; Cao, S. F.; Tong, L. J.; Wei, L. X.; Ding, J.; Xie, H.; Duan, W. H. Chin. Chem. Lett. 2016, 27, 200.
  (b) Wu, Z.; Yan, M.; Hu, S. H.; Yu, Z. C.; Zhu, Y.; Cheng, Y. D.; Liu, H. C.; Zhang, Y. M.; Yao, S. H.; Tang, W. F.; Lu, T. Chin. Chem. Lett. 2014, 25, 351.
6. [6]
  Liu, Y.; Gray, N. S. Nat. Chem. Biol. 2006, 2, 358. doi: 10.1038/nchembio799
7. [7]
  Das, D.; Sikdar, P.; Bairagi, M. Eur. J. Med. Chem. 2016, 109, 89. doi: 10.1016/j.ejmech.2015.12.022
8. [8]
  (a) Bharti, S. K.; Nath, G.; Tilak, R.; Singh, S. K. Eur. J. Med. Chem. 2010, 45, 651.
  (b) Qin, Y. J.; Wang, P. F.; Makawana, J. A.; Wang, Z. C.; Wang, Z. N.; Yan, G.; Jiang, A. Q.; Zhu, H. L. Bioorg. Med. Chem. Lett. 2014, 24, 5279.
9. [9]
  Coumar, M. S.; Chu, C. Y.; Lin, C. W.; Shiao, H. Y.; Ho, Y. L.; Reddy, R.; Lin, W. H.; Chen, C. H.; Peng, Y. H.; Leou, J. S.; Lien, T. W.; Huang, C. T.; Fang, M. Y.; Wu, S. H.; Wu, J. S.; Chittimalla, S. K.; Song, J. S.; Hsu, J. T.; Wu, S. Y.; Liao, C. C.; Chao, Y. S.; Hsieh, H. P. J. Med. Chem. 2010, 53, 4980. doi: 10.1021/jm1000198
10. [10]
  (a) Tseng, C. Magn. Reson. Chem. 1987, 25, 105.
  (b) Bramley, S. E.; Dupplin, V.; Goberdhan, D. G.; Meakins, G. D. J. Chem. Soc., Perkin Trans 1. 1987, 639.
  (c) Forlani, L.; Tocke, A. L.; Del Vecchio, E.; Lakhdar, S.; Goumont, R.; Terrier, F. J. Org. Chem. 2006, 71, 5527.
11. [11]
  Metzger, J. V. In Chemistry of Heterocyclic Compounds, Vol. 34, Part 2, Ed.:Metzger, J. V., New York, 1979, p. 17.
12. [12]
  Zhou, A.; Pittman, C. U. Tetrahedron Lett. 2005, 46, 3801. doi: 10.1016/j.tetlet.2005.03.205
13. [13]
  Yuan, M.; Liu, M.; Zhang, Y.; Yan, H.; Li, D.; Zhang, D.; Liu, H. Chin. J. Org. Chem. 2012, 32, 1746(in Chinese).
14. [14]
  (a) Wermuth, C. G. Drug Discovery Today 2006, 11, 348.
  (b) Martin, Y. C.; Kofron, J. L.; Traphagen, L. M. J. Med. Chem. 2002, 45, 4350.
  (c) Vainio, M. J.; Puranen, J. S.; Johnson, M. S. J. Chem. Inf. Model. 2009, 49, 492.
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