Synthesis and Bioactivity of Novel Pyrazole Oxime Ester Derivatives Containing Furan Moiety

doi:10.6023/cjoc201503001

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1785-1791.DOI: 10.6023/cjoc201503001 Previous Articles Next Articles

NOTE

新型含呋喃环结构的吡唑肟酯类化合物的合成及其生物活性

石玉军^a,b, 王森林^a, 何海兵^b, 李钰^b, 李阳^a, 方源^a, 戴红^b

a 江苏科技大学环境与化学工程学院镇江 212003;
b 南通大学化学化工学院南通 226019

收稿日期:2015-03-01 修回日期:2015-03-19 发布日期:2015-04-13
通讯作者: 石玉军, 戴红 E-mail:yjshi2015@163.com;daihong_2001@aliyun.com
基金资助:
国家自然科学基金(No. 21202089)和江苏省“六大人才高峰”(Nos. 2011-SWYY-009, 2013-SWYY-013)资助项目.

Synthesis and Bioactivity of Novel Pyrazole Oxime Ester Derivatives Containing Furan Moiety

Shi Yujun^a,b, Wang Senlin^a, He Haibing^b, Li Yu^b, Li Yang^a, Fang Yuan^a, Dai Hong^b

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

Received:2015-03-01 Revised:2015-03-19 Published:2015-04-13
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21202089) and the Research Foundation of the Six People Peak of Jiangsu Province (Nos. 2011-SWYY-009, 2013-SWYY-013).

1. Synthesis and Bioactivity of Novel Pyrazole Oxime Ester Derivatives Containing Furan Moiety.PDF(710KB)

Abstract

In search of novel heterocyclic compounds with potent biological activities, a series of novel pyrazole oxime ester derivatives bearing substituted furan ring were prepared by the reaction of 5-substituted phenyl-2-furan carbonyl chloride with different pyrazole oximes. The structures of the target compounds were characterized by ¹H NMR, ¹³C NMR and elemental analysis. The bioassay data exhibited that some title compounds showed certain acaricidal or insecticidal activities. For example, 5-(4-trifluoromethylphenyl)furan-2-formic acid-[1-methyl-3-methyl-5-(2,4-dichlorophenoxy)pyrazole-4-carbaldehyde]-oxime ester (6g) displayed 83% inhibition rate against Tetranychus cinnabarinus at the concentration of 400 μg/mL, and 5-(4-fluoro-phenyl)furan-2-formic acid-[1-(4-methylphenyl)-3-methyl-5-(4-methylphenoxy)pyrazole-4-carbaldehyde]oxime ester (6m) showed insecticidal activity against Plutella xylostella and Aphis craccivora with 71% and 64% mortality, respectively, at the same concentration.

Key words: furan, pyrazole oxime, synthesis, biological activity

Cite this article

Shi Yujun, Wang Senlin, He Haibing, Li Yu, Li Yang, Fang Yuan, Dai Hong. Synthesis and Bioactivity of Novel Pyrazole Oxime Ester Derivatives Containing Furan Moiety[J]. Chin. J. Org. Chem., 2015, 35(8): 1785-1791.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Hu, L. M.; Li, X. S.; Chen, Z. Y.; Liu, Z. J. Chin. J. Org. Chem. 2003, 23, 1131 (in Chinese). (胡利明, 李学恕, 陈致远, 刘钊杰, 有机化学, 2003, 23, 1131.)
[2] Zhang, X. Y.; Li, Y. S.; Weng, J. Q.; Tan, C. X. Chin. J. Org. Chem. 2011, 31, 1295 (in Chinese). (张向阳, 李永曙, 翁建全, 谭成侠, 有机化学, 2011, 31, 1295.)
[3] Li, Y. X.; Ling, L.; Chen, Q. Chin. J. Org. Chem. 2011, 31, 306 (in Chinese). (李元祥, 林龙, 陈琼, 有机化学, 2011, 31, 306.)
[4] Yan, T.; Yu, S. J.; Liu, P. F.; Liu, Z.; Wang, B. L.; Xiong, L. X.; Li, Z. M. Chin. J. Chem. 2012, 30, 919.
[5] Li, X.; Lu, X.; Xing, M.; Yang, X. H.; Zhao, T. T.; Gong, H. B.; Zhu, H. L. Bioorg. Med. Chem. Lett. 2012, 22, 3589.
[6] Xe, F.; Liu, T. T.; Yang, G.; Yuan, J.; Kong, X. L.; Xu, T. M.; Tan, C, X. Chin. J. Org. Chem. 2013, 33, 2596 (in Chinese). (谢峰, 刘婷婷, 杨果, 袁静, 孔小林, 许天明, 谭成侠, 有机化学, 2013, 33, 2596.)
[7] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[8] Ma, Q. S.; Liu, X. H.; Weng, J. Q.; Li, Y. S.; Zhang, M.; Zhang, X. Y.; Tan, C. X. Chin. J. Org. Chem. 2013, 33, 1749 (in Chinese). (马青森, 刘幸海, 翁建全, 李永曙, 张旻, 张向阳, 谭成侠, 有机化学, 2013, 33, 1749.)
[9] Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Simth, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[10] 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.
[11] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[12] Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[13] Zhao, P. L.; Wang, L.; Zhu, X. L.; Huang, X. Q.; Zhan, C. G.; Wu, J. W.; Yang, G. F. J. Am. Chem. Soc. 2010, 132, 185.
[14] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Qin, X.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1662 (in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 秦雪, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1662.)
[15] 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). (戴红, 于海波, 刘建兵, 秦雪, 王婷婷, 张欣, 秦振芳, 方建新, 有机化学, 2013, 33, 1104.)
[16] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[17] 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.
[18] Kim, Y. J.; Lee, S. H.; Lee, S. W.; Ahn, Y. J. Pest Manage. Sci. 2004, 60, 1001.
[19] Yang, H. Z.; Li, Q. Agrochemicals 2007, 46, 81 (in Chinese). (杨会芝, 李庆, 农药, 2007, 46, 81.)
[20] Sagratini, G.; Angeli, P.; Buccioni, M.; Gulini, U.; Marucci, G.; Melchiorre, C.; Leonardi, A.; Poggesi, E.; Giardina, D. Bioorg. Med. Chem. 2007, 15, 2334.
[21] Wang, Q. D.; Xue, S. J.; Shen, J. F.; Cai, Z. J. Chin. J. Org. Chem. 2008, 28, 521 (in Chinese). (王庆东, 薛思佳, 申杰峰, 蔡志娟, 有机化学, 2008, 28, 521.)
[22] Xue, S. J.; Bian, W. D.; Chai, A.; Yu, S. R. Chin. J. Chem. 2008, 26, 1501.
[23] Cui, Z. N.; Zhang, L.; Huang, J.; Ling, Y.; Yang, X. L. Chin. J. Org. Chem. 2010, 30, 1482 (in Chinese). (崔紫宁, 张莉, 黄娟, 凌云, 杨新玲, 有机化学, 2010, 30, 1482.)
[24] Cui, Z. N.; Ling, Y.; Li, B. J.; Li, Y. Q.; Rui, C. H.; Cui, J. R.; Shi, Y. X.; Yang, X. L. Molecules 2010, 15, 4267.
[25] Li. Y.; Li. B. J.; Yang, X. L.; Shi, Y. X.; Miao, H. J.; Ling, Y. Chin. J. Org. Chem. 2011, 31, 1411 (in Chinese). (李映, 李宝聚, 杨新玲, 石延霞, 苗宏健, 凌云, 有机化学, 2011, 31, 1411.)
[26] Cui, Z. N.; Shi, Y. X.; Cui, J. R.; Ling, Y.; Li, B. J.; Yang, X. L. Chem. Biol. Drug Des. 2012, 79, 121.
[27] 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.
[28] Ma, J. A.; Huang, R. Q.; Feng, L.; Song, J.; Qiu, D. W. Chem. Res. Chin. Univ. 2003, 19, 297.
[29] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[30] Drizin, I.; Gregg, R. J.; Scanio, M. J. C.; Shi, L.; Gross, M. F.; Atkinson, R. N.; Thomas, J. B.; Johnson, M. S.; Carroll, W. A.; Marron, B. E.; Chapman, M. L.; Liu, D.; Krambis, M. J.; Shieh, C. C.; Zhang, X. F.; Hemandez, G.; Gauvin, D. M.; Mikusa, J. P.; Zhu, C. Z.; Joshi, S.; Honore, P.; Marsh, K. C.; Roeloffs, R.; Wemess, S.; Krafte, D. S.; Jarvis, M. F.; Faltynek, C. R.; Kort, M. E. Bioorg. Med. Chem. 2008, 16, 6379.
[31] Cui, Z. N.; Li, Y.; Ling, Y.; Huang, J.; Cui, J. R.; Wang, R. Q.; Yang, X. L. Eur. J. Med. Chem. 2010, 45, 5576.

新型含呋喃环结构的吡唑肟酯类化合物的合成及其生物活性

Synthesis and Bioactivity of Novel Pyrazole Oxime Ester Derivatives Containing Furan Moiety

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Mengzhu Li, Boying Meng, Wenjie Lan, Bin Fu. Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 195-203.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[14]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[15]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.