Citation: Dai Hong, Yao Wei, Du Xianchao, Wang Xianglong, Wu Jinming, Chen Qingwen, Li Chunjian, Shi Jian, Zhang Haijun. Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Containing Substituted Tetrazolyl Group[J]. Chinese Journal of Organic Chemistry, ;2017, 37(12): 3267-3273. doi: 10.6023/cjoc201708026 shu

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Containing Substituted Tetrazolyl Group

Dai Hong ^a ,
Yao Wei ^a ,
Du Xianchao ^a ,
Wang Xianglong ^a ,
Wu Jinming ^a,, ,
Chen Qingwen ^a ,
Li Chunjian ^b ,
Shi Jian ^b ,
Zhang Haijun ^a,,

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

Corresponding author: Wu Jinming, ntgao2016@163.com Zhang Haijun, hjzh1893@163.com
Received Date: 13 August 2017
Revised Date: 6 September 2017
Available Online: 22 December 2017
Fund Project: Postgraduate Research and Practice Innovation Program of Jiangsu Province SJCX17_0640the Research Foundation of the Six People Peak of Jiangsu Province 2013-SWYY-013Project 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 Postgraduate Research and Practice Innovation Program of Jiangsu Province (No. SJCX17_0640)the National Natural Science Foundation of China 21372135

Figures(2)

In order to explore novel pyrazole oxime derivatives with potent biological activities, a series of novel pyrazole oximes carrying tetrazole unit were designed and synthesized by the method of active substructure combination. The structures of the title compounds were confirmed by ¹H NMR, ¹³C NMR, and elemental analysis. Preliminary bioassay data showed that some aimed compounds displayed good insecticidal activities. At the concentration of 500 μg/mL, ten compounds exhibited insecticidal activity against Oriental armyworm with 90%~100%, nine compounds had insecticidal activity against Aphis medicaginis with 80%~100%, ten compounds possessed insecticidal activity against Nilaparvata lugens with 80%~100%, and one compound exhibited 80% acaricidal activity against Tetranychus cinnabarinus. When the concentration was reduced to 100 μg/mL, one compound still showed insecticidal activity against Aphis medicaginis with 85%. Additionally, some compounds had certain fungicidal activity, at 200 μg/mL two compounds showed 60%~80% fungicidal activity against Pseudoperonospora cubensis.
- tetrazole,
- pyrazole oxime,
- synthesis,
- biological activity
1. [1]
  Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73. doi: 10.1006/pest.2000.2477
2. [2]
  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
3. [3]
  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).
4. [4]
  Dai, H.; Chen, J.; Hong, Y.; Yuan, B. Y.; Fan, C. G.; Ma, R. Y.; Liang, Z. P.; Shi, J. Chin. J. Org. Chem. 2017, 37, 1542(in Chinese).
5. [5]
  Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636. doi: 10.1021/jf060074f
6. [6]
  Dai, H.; Yu, H. B.; Liu, J. B.; Qin, X.; Wang, T. T.; Zhang, X.; Qin. Z. F.; Fang, J. X. Chin. J. Org. Chem. 2013, 33, 1104(in Chinese).
7. [7]
  Dai, H.; Ge, S. S.; Li, G.; Chen, J.; Shi, Y. J.; Ye, L. Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 4504. doi: 10.1016/j.bmcl.2016.07.068
8. [8]
  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, 10160. doi: 10.1021/jf802489e
9. [9]
  Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173. doi: 10.1584/jpestics.20.173
10. [10]
  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
11. [11]
  Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M. Pest. Manage. Sci. 2014, 70, 1207. doi: 10.1002/ps.2014.70.issue-8
12. [12]
  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
13. [13]
  Dai, H.; Chen, J.; Li, G.; Ge, S. S.; Shi, Y. J.; Fang, Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2017, 27, 950. doi: 10.1016/j.bmcl.2016.12.083
14. [14]
  Dai, H.; Shi, Y. J.; Yao, W.; Song, C.; Qian, H. W.; Wang, X. L.; Zhang, Z.; Han, X. D. CN 106946782, 2017[Chem. Abstr. 2017, 1158602].
15. [15]
  Li, S. X.; Wang, Y. G. Chin. J. Org. Chem. 2003, 23, 1311(in Chinese). doi: 10.3321/j.issn:0253-2786.2003.11.026
16. [16]
  Kavitha, H. P. Asian J. Chem. 2004, 16, 1191.
17. [17]
  Upadhayaya, R. S.; Jain, S.; Sinha, N.; Kishore, N.; Chandra, R.; Arora, S. K. Eur. J. Med. Chem. 2004, 39, 579. doi: 10.1016/j.ejmech.2004.03.004
18. [18]
  Sharon, A.; Pratap, R.; Tiwari, P.; Srivastava, A.; Maulik, P. R.; Ram, V. J. Bioorg. Med. Chem. Lett. 2005, 15, 2115. doi: 10.1016/j.bmcl.2005.02.060
19. [19]
  Jedhe, G. S.; Paul, D.; Gonnade, R. G.; Santra, M. K.; Hamel, E.; Nguyen, T. L.; Sanjayan, G. J. Bioorg. Med. Chem. Lett. 2013, 23, 4680. doi: 10.1016/j.bmcl.2013.06.004
20. [20]
  Maddila, S.; Pagadala, R.; Jonnalagadda, S. B. J. Heterocycl. Chem. 2015, 52, 487. doi: 10.1002/jhet.v52.2
21. [21]
  Ionescu, C.; Sippelli, S.; Toupet, L.; Barragan-Montero, V. Bioorg. Med. Chem. Lett. 2016, 26, 636. doi: 10.1016/j.bmcl.2015.11.059
22. [22]
  Lima, L. M. A.; Barreiro, E. J. Curr. Med. Chem. 2005, 12, 23. doi: 10.2174/0929867053363540
23. [23]
  Yan, M.; Shi, D. Q. Chin. J. Org. Chem. 2008, 28, 736(in Chinese).
24. [24]
  Bai, K.; Yao, C. P.; Chen, Q.; Shen, C.; Pei, W. Chin. J. Org. Chem. 2010, 30, 1255(in Chinese).
25. [25]
  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).
26. [26]
  Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hui, Y. H.; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinski, M. N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. J. Med. Chem. 2002, 45, 1697. doi: 10.1021/jm010523x
27. [27]
  Romagnoli, R.; Baraldi, P. G.; Salvador, M. K.; Preti, D.; Tabrizi, M. A.; Brancale, A.; Fu, X. H.; Li, J.; Zhang, S. Z.; Hamel, E.; Bortolozzi, R.; Basso, G.; Viola, G. J. Med. Chem. 2012, 55, 475.
28. [28]
  Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390. doi: 10.1021/jm9800853
29. [29]
  Park, M. S.; Park, H. J.; Park, K. H.; Lee, K. I. Synth. Commun. 2004, 34, 1541. doi: 10.1081/SCC-120030741
30. [30]
  Dai, H.; Chen, J.; Li, H.; Dai, B. J.; He, H. B.; Fang, Y.; Shi, Y. J. Molecules 2016, 21, 276. doi: 10.3390/molecules21030276
31. [31]
  Liu, T. T.; Ni, Y.; Zhong, L. K.; Huang, H. Y.; Hu, W. Q.; Xu, T. M.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 422(in Chinese).
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
4. [4]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
5. [5]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
6. [6]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
7. [7]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
8. [8]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
9. [9]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
10. [10]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
11. [11]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
12. [12]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
13. [13]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
14. [14]
  Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO₃ for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
15. [15]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
16. [16]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
17. [17]
  Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF模板法合成氮掺杂碳材料用于增强电化学钠离子储存和去除. Acta Physico-Chimica Sinica, 2025, 41(3): 2405002-. doi: 10.3866/PKU.WHXB202405002
18. [18]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
19. [19]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
20. [20]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(3228)
HTML views(455)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142