Citation: Sen-Lin Wang, Yu-Jun Shi, Hai-Bing He, Yu Li, Yang Li, Hong Dai. Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring[J]. Chinese Chemical Letters, ;2015, 26(6): 672-674. doi: 10.1016/j.cclet.2015.04.017 shu

Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring

Sen-Lin Wang ^a ,
Yu-Jun Shi ^a,b,, ,
Hai-Bing He ^b ,
Yu Li ^b ,
Yang Li ^a ,
Hong Dai ^b,,

1.
a School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China;
2.
b College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China

Corresponding author: Yu-Jun Shi, Hong Dai,
Received Date: 27 February 2015
Available Online: 30 March 2015
Fund Project: This study was funded by the National Natural Science Foundation of China (No. 21202089) (No. 21202089) the Research Foundation of the Six People Peak of Jiangsu Province (Nos. 2011-SWYY-009, 2013-SWYY-013) (Nos. 2011-SWYY-009, 2013-SWYY-013)the Technology Project Fund of Nantong City (Nos. AS2013004, CP12013002). (Nos. AS2013004, CP12013002)

A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by ¹H NMR, ¹³C NMR spectra and elemental analyses. Preliminary bioassay results showed that some of the title compounds displayed promising fungicidal activity besides insecticidal and acaricidal activity. Particularly, compound 8c exhibited potent fungicidal activity against cucumber Pseudoperonospora cubensis beyond good insecticidal activity against Aphis craccivora and Nilaparvata lugens.
- Pyrazole oxime,
- Substituted oxazole,
- Insecticidal activity,
- Acaricidal activity,
- Fungicidal activity
1. [1]
  [1] H.S. Chen, Z.M. Li, Y.F. Han, Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (thiadiazoles), J. Agric. Food Chem. 48 (2000) 5312-5315.
2. [2]
  [2] H. Dai, Y.Q. Li, D. Du, et al., Synthesis and biological activities of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety, J. Agric. Food Chem. 56 (2008) 10805-10810.
3. [3]
  [3] H.J. Song, Y.X. Liu, L.X. Xiong, et al., Design, synthesis, and insecticidal evaluation of new pyrazole derivatives containing imine, oxime ether, and dihydroisoxazoline groups based on the inhibitor binding pocket of respiratory complex I, J. Agric. Food Chem. 61 (2013) 8730-8736.
4. [4]
  [4] H. Dai, Y.S. Xiao, Z. Li, et al., The thiazoylmethoxy modification on pyrazole oximes: synthesis and insecticidal biological evaluation beyond acaricidal activity, Chin. Chem. Lett. 25 (2014) 1014-1016.
5. [5]
  [5] H.J. Ma, Y.H. Li, Q.F. Zhao, et al., Synthesis and herbicidal activity of novel N-(2,2,2)-trifluoroethylpyrazole derivatives, J. Agric. Food Chem. 58 (2010) 4356-4360.
6. [6]
  [6] S. Mert, R. Kasimogullari, T. Ica, et al., Synthesis, structure-activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives, Eur. J. Med. Chem. 78 (2014) 86-96.
7. [7]
  [7] K.M. Dawood, T.M.A. Eldebss, H.S.A. El-Zahabi, et al., Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents, Eur. J. Med. Chem. 70 (2013) 740-749.
8. [8]
  [8] M.B. Swanson, W.A. Ivancic, A.M. Saxena, et al., Direct photolysis of Fenpyroximate in a buffered aqueous solution under a xenon lamp, J. Agric. Food Chem. 43 (1995) 513-518.
9. [9]
  [9] H. Hamaguchi, O. Kajihara, M. Katoh, Development of a new acaricide, Fenpyroximate, J. Pestic. Sci. 20 (1995) 173-175.
10. [10]
  [10] K. Motoba, H. Nishizawa, T. Suzuki, et al., Species-specific detoxification metabolism of Fenpyroximate, a potent acaricide, Pestic. Biochem. Physiol. 67 (2000) 73-84.
11. [11]
  [11] P. Guo, J.H. Huang, Q.C. Huang, et al., Synthesis of novel 1,3-oxazole derivatives with insect growth-inhibiting activities, Chin. Chem. Lett. 24 (2013) 957-961.
12. [12]
  [12] G.Y. Li, X.H. Qian, J.N. Cui, et al., Synthesis and herbicidal activity of novel 3-aminocarbonyl-2-oxazolidinethione derivatives containing a substituted pyridine ring, J. Agric. Food Chem. 54 (2006) 125-129.
13. [13]
  [13] C.K. Ryu, R.Y. Lee, N.Y. Kim, et al., Synthesis and antifungal activity of benzo[-d]oxazole-4,7-diones, Bioorg. Med. Chem. Lett. 19 (2009) 5924-5926.
14. [14]
  [14] A.V. Gadakh, C. Pandit, S.S. Rindhe, et al., Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2-hydrobenzoyl)-1H-pyrazoles and pyrazolyl benzo[d]oxazoles, Bioorg. Med. Chem. Lett. 20 (2010) 5572-5576.
15. [15]
  [15] D. Sriram, P. Yogeeswari, R. Thirumurugan, et al., Discovery of new antitubercular oxazolyl thiosemicarbazones, J. Med. Chem. 49 (2006) 3448-3450.
16. [16]
  [16] Q.Q. Zhao, S.H. Liu, Y.H. Li, et al., Design, synthesis, and biological activities of novel 2-cyanoacrylates containing oxazole, oxadiazole, or quinoline moieties, J. Agric. Food Chem. 57 (2009) 2849-2855.
17. [17]
  [17] H.J. Park, K. Lee, S.J. Park, et al., Identification of antitumor activity of pyrazole oxime ethers, Bioorg. Med. Chem. Lett. 15 (2005) 3307-3312.
18. [18]
  [18] H. Dai, Y.F. Zhao, P. Niu, et al., Synthesis and biological activity of 1-{4-[(2-cyanoimino-1,3-thiazolidine-3-yl)methyl] thiazol-2-yl}-3-aroyl ureas, Chin. J. Org. Chem. 33 (2013) 1568-1572.
19. [19]
  [19] Y. Zhao, C.H. Mao, Y.Q. Li, et al., Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole, J. Agric. Food Chem. 56 (2008) 7326-7332.
20. [20]
  [20] X.S. Shao, H. Fu, X.Y. Xu, et al., Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities, J. Agric. Food Chem. 58 (2010) 2696-2702.
21. [21]
  [21] S. Tu, L.H. Xu, L.Y. Ye, et al., Synthesis and fungicidal activities of novel indenesubstituted oxime ether strobilurins, J. Agric. Food Chem. 56 (2008) 5247-5253.
1. [1]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
2. [2]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
3. [3]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
4. [4]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
5. [5]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
6. [6]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
7. [7]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
8. [8]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
9. [9]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
10. [10]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
11. [11]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
12. [12]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
13. [13]
  Meng Wang , Yan Zhang , Yunbo Yu , Wenpo Shan , Hong He . High-temperature calcination dramatically promotes the activity of Cs/Co/Ce-Sn catalyst for soot oxidation. Chinese Chemical Letters, 2025, 36(1): 109928-. doi: 10.1016/j.cclet.2024.109928
14. [14]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
15. [15]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
16. [16]
  Xiaoli Deng , Xiangchao Lu , Yang Cao , Qianjin Chen . Electrochemical imaging uncovers the heterogeneity of HER activity by sulfur vacancies in molybdenum disulfide monolayer. Chinese Chemical Letters, 2025, 36(3): 110379-. doi: 10.1016/j.cclet.2024.110379
17. [17]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
18. [18]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
19. [19]
  Shaobin He , Xiaoyun Guo , Qionghua Zheng , Huanran Shen , Yuan Xu , Fenglin Lin , Jincheng Chen , Haohua Deng , Yiming Zeng , Wei Chen . Engineering nickel-supported osmium bimetallic nanozymes with specifically improved peroxidase-like activity for immunoassay. Chinese Chemical Letters, 2025, 36(4): 110096-. doi: 10.1016/j.cclet.2024.110096
20. [20]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(664)
HTML views(0)

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