Citation: Rui Jian, Zhang Qi, Wang Xin, Xu Xu, Xu Haijun, Rao Weidong, Wang Shifa. Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 218-225. doi: 10.6023/cjoc201606038 shu

Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives

Rui Jian ^a ,
Zhang Qi ^a ,
Wang Xin ^b ,
Xu Xu ^a,c,d ,
Xu Haijun ^a ,
Rao Weidong ^a ,
Wang Shifa ^a,c,d,*,,

a.
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
b.
College of Plant Protection, Nanjing Agricultural University, Nanjing 210095
c.
Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037
d.
Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008

Corresponding author: Wang Shifa, wsfyyq@njfu.com.cn
Received Date: 24 June 2016
Revised Date: 4 August 2016

Fund Project: the Natural Science Foundation of the Jiangsu Higher Education Institutions of China 14KJ220001the National Natural Science Foundation of China 31470529the Open Funding of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products GXFC15-02

Figures(2)

Novel pinanyl pyrazole derivatives were synthesized from nopinone and their bioactivities were also examined in this paper.The intermediate compounds 3-arylidenenopinones 2a~2g were synthesized by condensation of aromatic aldehydes and nopinone, and pinanyl pyrazole derivatives 3a~3g were subsequently obtained by cyclization and dehydroaromatization of compounds 2a~2g and hydrazine hydrate in the circumstance of N, N-dimethylformamide (DMT).The target compound pinanyl pyrazole acetamide derivatives 4a~4g were synthesized by alkylation using 2-chloroacetamide as the alkylating agent under the condition of base catalysis.The structures of synthesized compounds were characterized by ¹H NMR, ¹³C NMR, IR, HRMS, and X-ray diffraction analysis.Biological activities evaluation of compounds 3a~3g and 4a~4g were performed including antibacterial and insecticidal activities on Tinocallis kahawaluokalani.Test results showed that compound 4g was a more potent bactericide and fungicide than others because of its good activities against bacteria and fungi; furthermore, compound 4g had shown the better insecticidal activity against Tinocallis kahawaluokalani than the others.
- nopinone,
- pinanyl pyrazole derivatives,
- bacteriostatic activity,
- insecticidal activity
1. [1]
  Abdel-Hafez, E. S. M. N.; Abuo-Rahma, E. D. A. A.; Abdel-Aziz, M.; Radwan, M. F.; Farag, H. H. Bioorg. Med. Chem. 2009, 17, 3829. doi: 10.1016/j.bmc.2009.04.037
2. [2]
  Christodoulou, M. S.; Liekens, S.; Kasiotis, K. M.; Haroutounian, S. A. Bioorg. Med. Chem. 2010, 18, 4338. doi: 10.1016/j.bmc.2010.04.076
3. [3]
  Gouda, M. A.; Berghot, M. A.; Shoeib, A. I.; Khalil, A. M. Eur. J. Med. Chem. 2010, 45, 1843. doi: 10.1016/j.ejmech.2010.01.021
4. [4]
  Cheng, Y.; Wang, H.; Dinesh, A.; Zhou, H. C. J. Org. Chem. 2016, 36, 1(in Chinese).
5. [5]
  Xia, Q. C.; He, Q. Z.; Xu, D. F.; Sun, D. Z.; Peng, Z. F. Acta Chim. Sinica 2010, 68, 2414(in Chinese).
6. [6]
  Gökhan-Kelekçi, N.; Yabanoğlu, S.; Küpeli, E.; Salgın, U.; Özen, O.; Uçar, G.; Yeşilada, E.; Kendi, E.; Yeşilada, A.; Bilgin, A. A. Bioorg. Med. Chem. 2007, 15, 5775. doi: 10.1016/j.bmc.2007.06.004
7. [7]
  Lv, P. C.; Li, H. Q.; Sun, J.; Zhou, Y.; Zhu, H. L. Bioorg. Med. Chem. 2010, 18, 4606. doi: 10.1016/j.bmc.2010.05.034
8. [8]
  Bandgar, B. P.; Gawande, S. S.; Bodade, R. G.; Gawande N. M.; Khobragade, C. N. Bioorg. Med. Chem. 2009, 17, 8168. doi: 10.1016/j.bmc.2009.10.035
9. [9]
  Farag, A. M.; Ali, K. A.; El-Debss, T. M.; Mayhoub, A. S.; Amr, A. G. E.; Abdel-Hafez, N. A.; Abdulla, M. M. Eur. J. Med. Chem. 2010, 45, 5887. doi: 10.1016/j.ejmech.2010.09.054
10. [10]
  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). doi: 10.6023/cjoc201406017
11. [11]
  Liu, X. H.; Bai, L. S.; Wang, S. F. Chin. J. Synth. Chem. 2006, 14, 147(in Chinese).
12. [12]
  Wen, L. R.; Li, M.; Jing, S. X. Chin. J. Org. Chem. 2005, 25, 197(in Chinese).
13. [13]
  Zhang, D. Q.; Xu, G. F.; Liu, Y. H.; Wang, D. Q.; Yang, X. L.; Yuan, D. K. J. Org. Chem. 2015, 35, 2191(in Chinese).
14. [14]
  Liu, J.; Xie, H. P.; Song, B. A. Chin. J. Org. Chem. 2010, 30, 1347(in Chinese).
15. [15]
  Bu, Y. Q.; Shan, Z. J.; Zhou, J. Y.; Lin, X. L. Agrochemicals 2009, 48, 399(in Chinese).
16. [16]
  Prakash, A.; Rao, J.; Nandagopal, V. J. Biopesticides 2008, 1, 154.
17. [17]
  Rufino, A. T.; Ribeiro, M.; Judas, F. J. Nat. Prod. 2014, 77, 264. doi: 10.1021/np400828x
18. [18]
  Rodrigues, K. A. D. F.; Amorim, L. V.; Dias, C. N.; Moraes, D. F. C.; Carneiro, S. M. P. J. Ethnopharmacol. 2015, 160, 32. doi: 10.1016/j.jep.2014.11.024
19. [19]
  Kim, D. S.; Lee, H. J.; Jeon, Y. D.; Han, Y. H.; Kee, J. Y.; Kim, H. J.; Kim, S. J. Am. J. Chin. Med. 2015, 43, 731. doi: 10.1142/S0192415X15500457
20. [20]
  Li, J.; Tian, X.; Gao, Y. J. RSC Adv. 2015, 5, 66947. doi: 10.1039/C5RA10660E
21. [21]
  Gao, Y.; Li, J.; Shang, S. Lett. Drug Des. Discovery 2015, 12, 241.
22. [22]
  Liu, B.; Wang, S. F. J. Nanjing For. Univ. 2010, 34, 89(in Chinese).
23. [23]
  Wei, B. S.; Xu, X.; Yang, Y. Q.; Cao, X. Q.; Wang, S. F. J. Org. Chem. 2012, 32, 287(in Chinese).
1. [1]
  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
2. [2]
  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
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]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
6. [6]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
7. [7]
  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
8. [8]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
9. [9]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
10. [10]
  Jiayu Gu , Siqi Wang , Jun Ling . Kinetics of Living Copolymerization: A Brief Discussion. University Chemistry, 2025, 40(4): 100-107. doi: 10.12461/PKU.DXHX202406012
11. [11]
  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
12. [12]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
13. [13]
  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
14. [14]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
15. [15]
  Congying Lu , Fei Zhong , Zhenyu Yuan , Shuaibing Li , Jiayao Li , Jiewen Liu , Xianyang Hu , Liqun Sun , Rui Li , Meijuan Hu . Experimental Improvement of Surfactant Interface Chemistry: An Integrated Design for the Fusion of Experiment and Simulation. University Chemistry, 2024, 39(3): 283-293. doi: 10.3866/PKU.DXHX202308097
16. [16]
  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
17. [17]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . 前驱体机械压实制备高密度活性炭及其致密电容储能性能. Acta Physico-Chimica Sinica, 2025, 41(3): 2406009-. doi: 10.3866/PKU.WHXB202406009
18. [18]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
19. [19]
  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
20. [20]
  Guanghui SUI , Yanyan CHENG . Application of rice husk-based activated carbon-loaded MgO composite for symmetric supercapacitors. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 521-530. doi: 10.11862/CJIC.20240221

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(574)
HTML views(41)

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