Notes

Synthesis and Bioactivity of Novel Cyanoacrylate Derivatives Containing Fluoride Methyl Pyrazole Moiety

  • Shi Yujun ,
  • Li Yang ,
  • Fang Yuan ,
  • Ye Linyu ,
  • Chen Jia ,
  • Dai Hong
Expand
  • aSchool 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 date: 2015-12-14

  Revised date: 2016-01-07

  Online published: 2016-02-02

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21202089, 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (Nos. 2011-SWYY-009, 2013-SWYY-013), and the Science and Technology Project Fund of Nantong City (Nos. AS2014011, CP12013002).

Abstract

In order to find novel cyanoacrylate lead compounds, 17 new cyanoacrylate compounds bearing fluoride methyl pyrazole moiety were synthesized by the method of active substructure combination. They were structurally confirmed by 1H NMR, 13C NMR and elemental analysis. The structures of compounds 7b, 7f, 7j and 7o were also tested through MS technique. Preliminary bioassay data showed that some of the target compounds displayed important anti-tumor activities.

Cite this article

Shi Yujun , Li Yang , Fang Yuan , Ye Linyu , Chen Jia , Dai Hong . Synthesis and Bioactivity of Novel Cyanoacrylate Derivatives Containing Fluoride Methyl Pyrazole Moiety[J]. Chinese Journal of Organic Chemistry, 2016 , 36(6) : 1431 -1437 . DOI: 10.6023/cjoc201512019

References

[1] Zhao, Y. G.; Huang, R. Q.; Cheng, M. R.; Li, H. Y.; Cheng, J. R. Chem. J. Chin. Univ. 1999, 19, 1620 (in Chinese). (赵毅刚, 黄润秋, 程慕如, 李慧英, 成俊然, 高等学校化学学报, 1999, 19, 1620.)
[2] Jin, L. H.; Zhong, H. M.; Song, B. A.; Hu, D. Y.; Yang, S.; Liu, G. Chin. J. Synth. Chem. 2005, 13, 113 (in Chinese). (金林红, 钟惠民, 宋宝安, 胡德禹, 杨松, 刘刚, 合成化学, 2005, 13, 113.)
[3] Wang, L. G.; Wang, F. Y.; Diao, Y. M.; Ni, J. P.; Wei, P. Chin. J. Org. Chem. 2005, 25, 1254 (in Chinese). (王龙根, 王凤云, 刁亚梅, 倪珏萍, 韦 萍, 有机化学, 2005, 25, 1254.)
[4] Song, B. A.; Yang, S.; Zhong, H. M.; Jin, L. H.; Hu, D. Y.; Lin, G. J. Fluorine Chem. 2005, 126, 87.
[5] Song, B. A.; Zhang, H. P.; Wang, H., Yang, S.; Jin, L. H.; Hu, D. Y.; Pang, L. L.; Xue, W. J. Agric. Food Chem. 2005, 53, 7886.
[6] Zou, X. M.; Yu, L. M.; Gao, Y.; Shi, H. L.; Fei, J.; Liu, B.; Li, H. F.; Hu, F. Z.; Yang, H. Z. Chin. J. Org. Chem. 2006, 26, 337 (in Chinese). (邹小毛, 郁丽敏, 高颍, 施欢乐, 裴江, 刘斌, 李慧芬, 胡方中, 杨华铮, 有机化学, 2006, 26, 337.)
[7] Liu, Y. X.; Cai, B. L.; Li, Y. H.; Song, H. B.; Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2007, 55, 3011.
[8] Wang, T. T.; Bing, G. F.; Zhang, X.; Qin, Z. F.; Yu, H. B.; Qin, X.; Dai, H.; Fang, J. X. Chin. J. Org. Chem. 2009, 29, 1287 (in Chinese). (王婷婷, 邴贵方, 张欣, 秦振芳, 于海波, 秦雪, 戴红, 方建新, 有机化学, 2009, 29, 1287.)
[9] Zhang, H.; Li, X. Y.; Hu, D. Y.; Yang, S.; Fan, H. T.; Wei, X.; Song, B. A. Chin. J. Org. Chem. 2011, 31, 1419 (in Chinese). (章浩, 李向阳, 胡德禹, 杨松, 范会涛, 宋宝安, 有机化学, 2011, 31, 1419.)
[10] Zhong, S. H.; Wang, C. F.; Song, Q. X.; Fan, M. L.; Liu, B. Y.; Wei, D. M.; Liu, J. B. Chin. J. Org. Chem. 2014, 34, 2324 (in Chinese). (钟世华, 王春凤, 宋青霞, 范明亮, 刘兵玉, 危冬梅, 刘建兵, 有机化学, 2014, 34, 2324.)
[11] Wang, X.; Wang, C. Q.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 92 (in Chinese). (王鑫, 王朝强, 傅翠蓉, 邹小毛, 有机化学, 2015, 35, 92.)
[12] Wu, S. S.; Miao, W. K.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2015, 35, 1484 (in Chinese). (吴珊珊, 苗文科, 王婷婷, 方建新, 有机化学, 2015, 35, 1484.)
[13] Zhao, Q. Q.; Liu, S. H.; Li, Y. H.; Wang, Q. M. J. Agric. Food Chem. 2009, 57, 2849.
[14] Ouyang, G. P.; Song, B. A.; Zhang, H. P.; Yang, S.; Jin, L. H.; Li, Q. Z.; Hu, D. Y. Molecules 2005, 10, 1351.
[15] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[16] Chen, L.; Ou, X. M.; Mao, C. H.; Shang, J.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Bioorg. Med. Chem. 2007, 15, 3678.
[17] Ouyang, G. P.; Chen, Z.; Cai, X. J.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. Bioorg. Med. Chem. 2008, 16, 9699.
[18] 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.
[19] Dai, H.; Shi, L.; Zhang, H. J.; Li, Y. Q.; Fang, J. X.; Shi, Y. J. Chin. J. Org. Chem. 2012, 32, 1060 (in Chinese). (戴红, 施磊, 张海军, 李永强, 方建新, 石玉军, 有机化学, 2012, 32, 1060.)
[20] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[21] Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347.
[22] Teng, M.; Zhu, J. J.; Johnson, M. D.; Chen, P.; Kornmann, J.; Chen, E. T.; Blasina, A.; Register, J.; Anderes, K.; Rogers, C.; Deng, Y. L.; Ninkovic, S.; Grant, S.; Hu, Q. Y.; Lundgren, K.; Peng, Z. W.; Kania, R. S. J. Med. Chem. 2007, 50, 5253.
[23] Liu, J. C.; Cui, Z. P.; He, H. W. Chin. J. Org. Chem. 2012, 32, 1925 (in Chinese). (刘建超, 崔泽平, 贺红武, 有机化学, 2012, 32, 1925.)
[24] 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). (刘婷婷, 倪芸, 钟良坤, 黄红英, 胡伟群, 许天明, 谭成侠, 有机化学, 2015, 35, 422.)
[25] Cai, F.; Zheng, Z. W.; Ji, W. J.; Xing, J. H.; Kong, X. L.; Tan, C. X.; Xu, T. M. Chin. J. Pestic. 2012, 51, 642 (in Chinese). (蔡飞, 郑志文, 姬文娟, 邢家华, 孔小林, 谭成侠, 许天明, 农药, 2012, 51, 642.)
[26] Peng, H.; Gao, Y. J.; He, H. W. Chin. J. Org. Chem. 2013, 33, 1994 (in Chinese). (彭浩, 高玉焦, 贺红武, 有机化学, 2013, 33, 1994.)
[27] Qing, F. L. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.)
[28] Stierli, D.; Walter, H.; Rajan, R. WO 2009127726, 2009 [Chem. Abstr. 2009, 151, 470195].
[29] Stierli, D.; Taylor, J. J.; Walter, H.; Worthington, P. A. WO 2007134799, 2008 [Chem. Abstr. 2008, 148, 168714].
[30] Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q. J. Agric. Food Chem. 2003, 51, 5030.
[31] Liu, J. C.; Liu, Y. J.; He, H. W. Chin. J. Org. Chem. 2015, 35, 462 (in Chinese). (刘建超, 刘勇军, 贺红武, 有机化学, 2015, 35, 462.)

Outlines

/