Citation: Dai Hong, Chen Jia, Hong Yu, Yuan Binying, Fan Chongguang, Ma Ruiyuan, Liang Zhipeng, Shi Jian. Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1542-1547. doi: 10.6023/cjoc201701042 shu

Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety

Dai Hong ^a ,
Chen Jia ^a ,
Hong Yu ^a ,
Yuan Binying ^a ,
Fan Chongguang ^a,*,, ,
Ma Ruiyuan ^a ,
Liang Zhipeng ^b ,
Shi Jian ^b,*,,

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

Corresponding author: Fan Chongguang, ntfcg@ntu.edu.cn Shi Jian, gaohbhe2015@aliyun.com
Received Date: 20 January 2017
Revised Date: 21 February 2017

Fund Project: the Science and Technology Project Fund of Nantong City CP12013002the National Natural Science Foundation of China 21372135the Research Foundation of the Six People Peak of Jiangsu Province 2013-SWYY-013the Science and Technology Project Fund of Nantong City MS22015020

Figures(2)

In order to explore novel pyrazole derivatives with good biological activities, a series of novel pyrazole oxime ester compounds containing pyridyl moiety were designed and synthesized according to the method of active substructure combination. The structures of the target compounds were determined by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay data indicated that some of the title compounds showed certain insecticidal activities. At a concentration of 500 μg/mL, seven compounds exhibited insecticidal activity against Oriental armyworm with 50%~90%, and six compounds exhibited insecticidal activity against Aphis medicaginis with 50%~90%. When the dosage was lowered to 100 μg/mL, 1, 3-dimethyl-5-(4-chlorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5f) and 1, 3-dimethyl-5-(4-methylphenoxy)pyra-zole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5j) were still active against Aphis medicaginis with inhibitory values of 50% and 50%, respectively. Insecticidal activities against Nilaparvata lugens of 1, 3-dimethyl-5-(3-fluorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5b) and 5f were both 100% at 500 μg/mL. Additionally, 1, 3-dimethyl-5-(4-fluorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5c), 1, 3-dimethyl-5-(3-chlorophenoxy)-pyrazole-4-for-myl-O-(2-chloropyridin-3-formyl)oxime (5e), 1, 3-dimethyl-5-(4-trifluoromethoxyphenoxy)pyrazole-4-formyl-O-(2-chloro-pyridin-3-formyl)oxime (5i) and 5j displayed good anti-tumor activity against HepG2 cells with IC₅₀ values of 2.6, 4.6, 1.8和1.1 μmol/L, respectively.
- pyridine,
- pyrazole,
- synthesis,
- biological activity
1. [1]
  Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636. doi: 10.1021/jf060074f
2. [2]
  Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805. doi: 10.1021/jf802429x
3. [3]
  Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173. doi: 10.1584/jpestics.20.173
4. [4]
  Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73. doi: 10.1006/pest.2000.2477
5. [5]
  Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307. doi: 10.1016/j.bmcl.2005.03.082
6. [6]
  Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173. doi: 10.1584/jpestics.20.173
7. [7]
  Swanson, M. B.; Ivancic, W. A.; Saxena, A. M.; Allton, J. D.; O'Brien, G. K.; Suzuki, T.; Nishizawa, H.; Nokata, M. J. Agric. Food Chem. 1995, 43, 513. doi: 10.1021/jf00050a048
8. [8]
  Lahm, G. P., Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898. doi: 10.1016/j.bmcl.2005.08.034
9. [9]
  Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E. Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347. doi: 10.1021/jm960803q
10. [10]
  Teng, M.; Zhu, J. J.; Johnson, M. D.; Chen, P.; Kornmann, J.; Chen, E. T.; Blasina, A.; Register, J.; Anderes, K.; Rogers, C.; Deng, Y. L.; Ninkovic, S.; Grant, S.; Hu, Q. Y.; Lundgren, K.; Peng, Z. W.; Kania, R. S. J. Med. Chem. 2007, 50, 5253. doi: 10.1021/jm0704604
11. [11]
  Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 60.
12. [12]
  Dai, H.; Shi, L.; Zhang, H. J.; Li, Y. Q.; Fang, J. X.; Shi, Y. J. Chin. J. Org. Chem. 2012, 32, 1060 (in Chinese).
13. [13]
  Wang, X.; Wang, C. Q.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 92 (in Chinese).
14. [14]
  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).
15. [15]
  Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric. Food Chem. 2007, 55, 2288. doi: 10.1021/jf063418a
16. [16]
  Lu, S. Y.; Shao, X. S.; Li, Z.; Xu, Z. P.; Zhao, S. S.; Wu, Y. L.; Xu, X. Y. J. Agric. Food Chem. 2012, 60, 322. doi: 10.1021/jf203068a
17. [17]
  Selby, T. P.; Lahm, G. P.; Stevenson, T. M.; Hughes, K. A.; Cordova, D.; Annan, I. B.; Barry, J. D.; Benner, E. A.; Currie, M. J.; Pahutski, T. F. Bioorg. Med. Chem. Lett. 2013, 23, 6341. doi: 10.1016/j.bmcl.2013.09.076
18. [18]
  Song, B. A.; Liu, X. H.; Yang, S.; Hu, D. Y.; Jin, L. H.; Zhang, Y. T. Chin. J. Org. Chem. 2005, 25, 507 (in Chinese). doi: 10.3321/j.issn:0253-2786.2005.05.003
19. [19]
  Ouyang, G. P.; Chen, Z.; Cai, X. J.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y., Zeng, S. Bioorg. Med. Chem. 2008, 16, 9699. doi: 10.1016/j.bmc.2008.09.070
20. [20]
  Shi, Y. J.; Wang, S. L.; He, H. B.; Li, Y.; Li, Y.; Fang, Y.; Dai, H. Chin. J. Org. Chem. 2015, 35, 1785 (in Chinese).
21. [21]
  Dai, H.; Li, H.; Jin. Z. C.; Liu, W. Y.; Xiao, Y.; He, H. B.; Wang, Q. M.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 185 (in Chinese).
22. [22]
  Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730. doi: 10.1021/jf402719z
23. [23]
  Liu, X. H.; Cui, P.; Song, B. A.; Bhadury, P. S.; Zhu, H. L.; Wang, S. F. Bioorg. Med. Chem. 2008, 16, 4075. doi: 10.1016/j.bmc.2008.01.035
24. [24]
  Park, M. S.; Park, H. J.; Park, K. H.; Lee, K. I. Synth. Commun. 2004, 34, 1541. doi: 10.1081/SCC-120030741
25. [25]
  Ma, J. A.; Huang, R. Q.; Feng, L.; Song, J.; Qiu, D. W. Chem. Res. Chin. Univ. 2003, 19, 297.
26. [26]
  Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014. doi: 10.1016/j.cclet.2014.06.011
27. [27]
  Liu, J. C.; Liu, Y. J.; He, H. W. Chin. J. Org. Chem. 2015, 35, 462 (in Chinese).
28. [28]
  Song, B. A.; Yang, S.; Zhong, H. M.; Jin, L. H.; Hu, D. Y.; Liu, G. J. Fluorine Chem. 2015, 126, 87.
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