Chinese Journal of Organic Chemistry >
Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives
Received date: 2016-06-24
Revised date: 2016-08-04
Online published: 2016-09-01
Supported by
Project supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China(No. 14KJ220001), the National Natural Science Foundation of China(No. 31470529), and the Open Funding of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products(No. GXFC15-02).
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.
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
[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.
[2] Christodoulou, M. S.; Liekens, S.; Kasiotis, K. M.; Haroutounian, S. A. Bioorg. Med. Chem. 2010, 18, 4338.
[3] Gouda, M. A.; Berghot, M. A.; Shoeib, A. I.; Khalil, A. M. Eur. J. Med. Chem. 2010, 45, 1843.
[4] Cheng, Y.; Wang, H.; Dinesh, A.; Zhou, H. C. J. Org. Chem. 2016, 36, 1(in Chinese).(程宇, 王辉, Dinesh Addla, 周成合, 有机化学, 2016, 36, 1.)
[5] Xia, Q. C.; He, Q. Z.; Xu, D. F.; Sun, D. Z.; Peng, Z. F. Acta Chim. Sinica 2010, 68, 2414(in Chinese).(夏庆春, 何其庄, 许东芳, 孙大志, 彭子飞, 化学学报, 2010, 68, 2414.)
[6] Gökhan-Kelekçi, N.; Yabano?lu, S.; Küpeli, E.; Salg?n, U.; Özen, O.; Uçar, G.; Ye?ilada, E.; Kendi, E.; Ye?ilada, A.; Bilgin, A. A. Bioorg. Med. Chem. 2007, 15, 5775.
[7] Lv, P. C.; Li, H. Q.; Sun, J.; Zhou, Y.; Zhu, H. L. Bioorg. Med. Chem. 2010, 18, 4606.
[8] Bandgar, B. P.; Gawande, S. S.; Bodade, R. G.; Gawande N. M.; Khobragade, C. N. Bioorg. Med. Chem. 2009, 17, 8168.
[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.
[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).(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.)
[11] Liu, X. H.; Bai, L. S.; Wang, S. F. Chin. J. Synth. Chem. 2006, 14, 147(in Chinese).(刘新华, 白林山, 王世范, 合成化学, 2006, 14, 147.)
[12] Wen, L. R.; Li, M.; Jing, S. X. Chin. J. Org. Chem. 2005, 25, 197(in Chinese).(文丽荣, 李明, 景淑霞, 有机化学, 2005, 25, 197.)
[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).(张大强, 徐高飞, 刘艳红, 王道全, 杨新玲, 袁德凯, 有机化学, 2015, 35, 2191.)
[14] Liu, J.; Xie, H. P.; Song, B. A. Chin. J. Org. Chem. 2010, 30, 1347(in Chinese).(刘杰, 谢化鹏, 宋宝安, 有机化学, 2010, 30, 1347.)
[15] Bu, Y. Q.; Shan, Z. J.; Zhou, J. Y.; Lin, X. L. Agrochemicals 2009, 48, 399(in Chinese).(卜元卿, 单正军, 周军英, 林小丽, 农药, 2009, 48, 399.)
[16] Prakash, A.; Rao, J.; Nandagopal, V. J. Biopesticides 2008, 1, 154.
[17] Rufino, A. T.; Ribeiro, M.; Judas, F. J. Nat. Prod. 2014, 77, 264.
[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.
[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.
[20] Li, J.; Tian, X.; Gao, Y. J. RSC Adv. 2015, 5, 66947.
[21] Gao, Y.; Li, J.; Shang, S. Lett. Drug Des. Discovery 2015, 12, 241.
[22] Liu, B.; Wang, S. F. J. Nanjing For. Univ. 2010, 34, 89(in Chinese).(刘兵, 王石发, 南京林业大学学报, 2010, 34, 89.)
[23] Wei, B. S.; Xu, X.; Yang, Y. Q.; Cao, X. Q.; Wang, S. F. J. Org. Chem. 2012, 32, 287(in Chinese).(魏柏松, 徐徐, 杨益琴, 曹晓琴, 王石发, 有机化学, 2012, 32, 287.)
/
| 〈 |
|
〉 |
