Chinese Journal of Organic Chemistry >
Synthesis and Bioactivity of Novel Pyrazole Oxime Ester Derivatives Containing Furan Moiety
Received date: 2015-03-01
Revised date: 2015-03-19
Online 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).
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
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]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1785 -1791 . DOI: 10.6023/cjoc201503001
[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.
/
| 〈 |
|
〉 |
