Citation: Zhou Jiahua, Dai Hong, Qian Hongwei, Du Xianchao, Mao Xinyu, Shi Yujun, Feng Hao, Shi Jian, Yao Yong. Synthesis and Biological Activity of New Cyanoacrylate Compounds Bearing Oxazole Moiety[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2122-2129. doi: 10.6023/cjoc201805036 shu

Synthesis and Biological Activity of New Cyanoacrylate Compounds Bearing Oxazole Moiety

Zhou Jiahua ^a ,
Dai Hong ^a,, ,
Qian Hongwei ^a ,
Du Xianchao ^a ,
Mao Xinyu ^a ,
Shi Yujun ^a,, ,
Feng Hao ^a ,
Shi Jian ^b ,
Yao Yong ^a,,

a.
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019
b.
Analysis and Testing Center, Nantong University, Nantong 226019

Corresponding author: Dai Hong, dh123@ntu.edu.cn Shi Yujun, yjshi2015@163.com Yao Yong, yaoyong1986@ntu.edu.cn
Received Date: 16 May 2018
Revised Date: 27 June 2018
Available Online: 29 August 2018
Fund Project: the Science and Technology Project Fund of Nantong City MS22015020the National Natural Science Foundation of China 21372135Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013), and the Science and Technology Project Fund of Nantong City (No. MS22015020) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201810304016Z)the Research Foundation of the Six People Peak of Jiangsu Province 2013-SWYY-013the Science and Technology Innovation Foundation for the College Students of Jiangsu Province 201810304016Z

Figures(2)

In order to find novel cyanoacrylate derivatives possessing potent bioactivities, a series of novel cyanoacrylates bearing substituted oxazole unit were designed and prepared. The bioassay data indicated that most title compounds had satisfactory herbicidal activities. At the dosage of 750 g/ha, some compounds showed herbicidal activity against Brassica juncea with 80%~100%, Chenopodium serotinum L. with 90%~100%, and Rumex acetosa L. with 80%~100%. 2-Cyano-3-me-thylthio-3-{[4-(2-(4-fluorophenyl)oxazole-4-yl)methylthio]-benzylanimo}acrylic acid (2-methoxy)ethyl ester (11a) and 2-cyano-3-methylthio-3-{[4-(2-(3, 4-difluorophenyl)oxazole-4-yl)methylthio]-benzylanimo}acrylic acid (2-methoxy)ethyl ester (11e) displayed herbicidal activity against Alopecurus aequalis Sobol with 70% and 60%, and Polypogon fugax Nees ex Steud with 70% and 60%. Compound 11a showed herbicidal activity against Poa acroleuca Steud with 70%. In addition, the inhibitory rates of compound 11a against Brassica juncea and Rumex acetosa L. were both 40% at the dosage of 150 g/ha.
- cyanoacrylate,
- oxazole unit,
- preparation,
- biological activity
1. [1]
  Liu, H. Y.; Tan, H. F.; Yang, H. Z. Chem. J. Chin. Univ. 2000, 21, 1855.(in Chinese). doi: 10.3321/j.issn:0251-0790.2000.12.037
2. [2]
  Song, B. A.; Yang, S.; Zhong, H. M.; Jin, L. H.; Hu, D. Y.; Lin, G. J. Fluorine Chem. 2005, 126, 87. doi: 10.1016/j.jfluchem.2004.10.041
3. [3]
  Ouyang, G. P.; Song, B. A.; Zhang, H. P.; Yang, S.; Jin, L. H.; Li, Q. Z.; Hu, D. Y. Molecules 2005, 10, 1351. doi: 10.3390/10101351
4. [4]
  Zhong, S. H.; Wang, C. F.; Song, Q. X.; Fan, M. L.; Liu, B. Y.; Wei, D. M.; Liu, J. B. Chin. J. Org. Chem. 2014, 34, 2324. (in Chinese).
5. [5]
  Wang, X.; Wang, C. Q.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 92. (in Chinese).
6. [6]
  Wu, S. S.; Miao, W. K.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2015, 35, 1484. (in Chinese).
7. [7]
  Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q. J. Agric. Food Chem, 2003, 51, 5030. doi: 10.1021/jf034067s
8. [8]
  Liu, Y. X.; Cao, B. L.; Li, Y. H.; Song, H. B.; Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2007, 55, 3011. doi: 10.1021/jf0636519
9. [9]
  Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Chin. J. Org. Chem. 2016, 36, 2472. (in Chinese).
10. [10]
  Dai, H.; Chen, J.; Hong, Yu.; Yuan, B. Y.; Chen, Y. M.; Shi, Y. J.; Ma, R. Y.; Liang, Z. P.; Shi, J. Chin. J. Org. Chem. 2017, 37, 739. (in Chinese).
11. [11]
  Song, B. A.; Zhang, H. P.; Wang, H.; Yang, S.; Jin, L. H.; Hu, D. Y.; Pang, L. L.; Xue, W. J. Agric. Food Chem. 2005, 53, 7886. doi: 10.1021/jf051050w
12. [12]
  Prakash, T. B.; Reddy, G. D.; Padmaja, A.; Padmavathi, V. Eur. J. Med. Chem. 2014, 82, 347. doi: 10.1016/j.ejmech.2014.06.001
13. [13]
  Guan, A. Y.; Qin, Y. K.; Wang, J. F.; Li, B. J. Fluorine Chem. 2013, 156, 120. doi: 10.1016/j.jfluchem.2013.09.003
14. [14]
  Wang, M. M.; Zhang, Q. Q.; Yue, K.; Li, Q. S.; Xu, F. B. Chin. J. Org. Chem. 2017, 37, 1774.(in Chinese).
15. [15]
  Li, G. Y.; Qian, X. H.; Cui, J. N.; Huang, Q. C.; Zhang, R.; Guan, H. J. Agric. Food Chem. 2006, 54, 125. doi: 10.1021/jf051928j
16. [16]
  Ohnmacht, S. A.; Ciancimino, C.; Vignaroli, G.; Gunaratnam, M.; Neidle, S. Bioorg. Med. Chem. Lett. 2013, 23, 5351. doi: 10.1016/j.bmcl.2013.07.057
17. [17]
  Robles, A. J.; McCowen, S.; Cai, S. X.; Glassman, M.; Ruiz, F.; Cichewicz, R. H.; McHardy, S. F.; Mooberry, S. L. J. Med. Chem. 2017, 60, 9275. doi: 10.1021/acs.jmedchem.7b01228
18. [18]
  Fuwa, H.; Noguchi, T.; Kawakami, M.; Sasaki, M. Bioorg. Med. Chem. Lett. 2014, 24, 2415. doi: 10.1016/j.bmcl.2014.04.031
19. [19]
  Xiao, L. W.; Zhang, G. X.; Jing, X. M.; Zhou, Q. X.; Feng, R. Chin. J. Org. Chem. 2016, 36, 1000. (in Chinese).
20. [20]
  Andrade, S. F.; Oliveira, B. G.; Pereira, L. C.; Ramos, J. P.; Joaquim, A. R.; Steppe, M.; Souza-Fagundes, E. M.; Alves, R. J. Eur. J. Med. Chem. 2017, 138, 13. doi: 10.1016/j.ejmech.2017.06.022
21. [21]
  Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672. doi: 10.1016/j.cclet.2015.04.017
22. [22]
  Dai, H.; Zhuang, H. Y.; Shi, L.; Li, G.; Zhang, H. J.; Fang, Y.; Dai, B. J. Chin. J. Org. Chem. 2015, 35, 2399. (in Chinese).
23. [23]
  Shi, Y. J.; Li, Y.; Fang, Y.; Ye, L. Y.; Chen, J.; Dai, H. Chin. J. Org. Chem. 2016, 36, 1431. (in Chinese).
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