新型蒎烷基吡唑酰胺类衍生物的合成及其生物活性研究
收稿日期: 2016-06-24
修回日期: 2016-08-04
网络出版日期: 2016-09-01
基金资助
江苏省高校自然科学研究重大项目（No. 14KJ220001）、国家自然科学基金（No. 31470529）和广西林产化学与工程重点实验室开放基金（No. JSBEM2014010）资助项目.
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).
以诺蒎酮为原料，合成了新型蒎烷基吡唑酰胺类衍生物，并对其生物活性进行了研究.诺蒎酮与芳香醛进行缩合反应，得到中间体3-芳亚甲基诺蒎酮2a~2g，2a~2g与水合肼经环化、脱氢芳构化反应，得到新型蒎烷基吡唑类化合物3a~3g；以N，N-二甲基甲酰胺为溶剂，3a~3g与2-氯乙酰胺在碱催化作用下，合成了7种吡唑酰胺类化合物4a~4g.其结构经1H NMR，13C NMR，IR，和HRMS表征.通过X射线衍射分析测定了化合物2-（6'，6'-二甲基-3'-（4'-甲氧基苯基）-4'，5'，6'，7'-四氢-5'，7'-桥亚甲基-吲唑-1'-基）乙酰胺（4d）的晶体结构.探讨了化合物3a~3g和4a~4g的抑菌活性和对蚜虫的杀虫活性.实验结果表明，2-（6'，6'-二甲基-3'-（4'-氟苯基）-4'，5'，6'，7'-四氢-5'，7'-桥亚甲基-吲唑-1'-基）乙酰胺（4g）既具有较好的抑菌效果，同时对紫薇蚜虫也表现出较好的杀虫活性.
芮坚 , 张齐 , 王欣 , 徐徐 , 徐海军 , 饶卫东 , 王石发 . 新型蒎烷基吡唑酰胺类衍生物的合成及其生物活性研究[J]. 有机化学, 2017 , 37(1) : 218 -225 . DOI: 10.6023/cjoc201606038
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.
[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.)
/
| 〈 |
|
〉 |
