含氮杂吲哚骨架的噻唑啉化合物的合成和抗菌活性
收稿日期: 2015-07-12
修回日期: 2015-08-19
网络出版日期: 2015-09-17
基金资助
国家“十二五”科技支撑计划(No. 2011BAE06B02)、国家自然科学基金(No. 21172255)资助项目.
Synthesis and Fungicidal Activities of Azaindolyl Thiazoline Compounds
Received date: 2015-07-12
Revised date: 2015-08-19
Online published: 2015-09-17
Supported by
Project supported by the National S&T Pillar Program of China (No. 2011BAE06B02), and the National Natural Science Foundation of China (No. 21172255).
麻红利 , 闫晓静 , 肖玉梅 , 袁德凯 , 张振华 , 傅滨 , 袁会珠 . 含氮杂吲哚骨架的噻唑啉化合物的合成和抗菌活性[J]. 有机化学, 2016 , 36(1) : 158 -164 . DOI: 10.6023/cjoc201507009
In order to find new agrochemical products with high activities, 20 azaindolyl thiazoline compounds were designed and synthesized, and their structures were identified by spectral methods. At the concentration of 50 mg/L, some of the title compounds showed good fungicidal activities. Among those compounds, the EC50 values of 2a and 2d against Phomopsis asparagi and Pyricularia oryzae Cav are 6.55 and 9.66 mg/L, which are superior or comparable to the control pesticides, then they can serve as the lead compounds for new fungicide discovery.
Key words： azaindolyl; thiazoline; synthesis; fungicidal activity
[1] (a) Maryanoff, B. E. Acc. Chem. Res. 2006, 39, 831.(b) Lu, H. Tonge, P. J. Acc. Chem. Res.2008, 41, 11.
[2] (a) Ye, N.; Neumeyer, J. L.; Baldessarini, R. J.; Zhen, X. C.; Zhang, A. Chem. Rev. 2013, 113, 123.(b) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem.Rev. 2010, 110, 4489.
[3] (a) Tan, X.; Zhou, Y.; Yao, Q. Z. World Notes Antibiot. 2010, 31, 207 (in Chinese).(谭雪, 周莹, 姚启正, 国外医药抗生素分册, 2010, 31, 207.)(b) Fan, J.-C.; Ren, A.-M.; Feng, J.-K.; Bo, D.-S. Chem. J. Chin. Univ. 2006, 27, 1091 (in Chinese).(范建训, 任爱民, 封继康, 薄冬生, 高等学校化学学报, 2006, 27, 1091.)(c) Tian, H.-B.; Yin, R.; Zhang, C.-F.; Zhang, L.; Li, J.-L.; Wang, L.-H.; Zhou, W.; Wang, X.-Y.; Guo, Z.-L. Chin. J. Med. Chem. 2002, 12, 214 (in Chinese).(田海滨, 尹端, 张春富, 张岚, 李俊玲, 王丽华, 周伟, 汪勇先, 郭子丽, 中国药物化学杂志, 2002, 12, 214.)
[4] (a) Wang, T.; Yin, Z.-W.; Zhang, Z.-X.; Bender, J. A.; Yang, Z.; Johnson, G.; Zheng Y.-Z.; Zadjura, L. M.; D'Arienzo, C. J.; Parker, D. D.; Gesenberg, C.; Yamanaka, G. A.; Gong, Y.-F.; Ho, H.-T.; Fang, H.; Zhou, N.-N.; McAuliffe, B. V.; Eggers, B. J.; Fan, L.; Nowicka-Sans, B.; Dicker, I. B.; Gao, Q.; Colonno, R. J.; Lin, P.-F.; Meanwell, N. A.; Kadow, J. F. J. Med. Chem. 2009, 52, 7778.(b) Choi-Sledeski, Y. M.; Kearney, R.; Poli, G.; Pauls, H.; Gardner, C.; Gong, Y.; Becker, M.; Davis, R.; Spada, A.; Liang, G. -Y.; Chu, V.; Brown, K.; Collussi, D.; Leadley, R., Jr.; Rebello, S.; Moxey, P.; Morgan, S.; Bentley, R.; Kasiewski, C.; Maignan, S.; Guilloteau, J.-P.; Mikol, V. J. Med. Chem. 2003, 46, 681.(c) Riether, D.; Harcken, C.; Razavi, H.; Kuzmich, D.; Gilmore, T.; Bentzien, J.; Pack, E. J. Jr.; Souza, D.; Nelson, R. M.; Kukulka, A.; Fadra, T. N.; Zuvela-Jelaska, L.; Pelletier, J.; Dinallo, R.; Panzenbeck, M.; Torcellini, C.; Nabozny, G. H.; Thomson, D. S. J. Med. Chem. 2010, 53, 6681.(d) Ganser, C.; Lauermann, E.; Maderer, A.; Stauder, T.; Kramb, J.-P.; Plutizki, S.; Kindler, T.; Moehler, M.; Dannhardt, G. J. Med.Chem. 2012, 55, 9531.(e) Gourdain, S.; Dairou, J.; Denhez, C.; Bui, L. C.; Rodrigues-Lima, F.; Janel, N.; Delabar, J. M.; Cariou, K.; Dodd, R. H. J. Med. Chem. 2013, 56, 9569.
[5] (a) Zhu, Y.-Q.; Wang, D.-Y.; Yuan, Y.-W.; Ma, Y.; Zou, X.-M.;Yang, H.-Zh. Chin. J. Org. Chem. 2012, 32, 2115 (in Chinese).(朱有全, 王丹阳, 袁燕伟, 马原, 邹小毛, 杨华铮, 有机化学, 2012, 32, 2115.)(b) Dai, H.; Miao, W.-K.; Liu, J.-B.; Wu, S.-S.; Qin, X.; Zhang, X.; Fang, J.-X. Chin. J. Org. Chem. 2012, 32, 1327 (in Chinese).(戴红, 苗文科, 刘建兵, 吴珊珊, 秦雪, 张欣, 方建新, 有机化学, 2012, 32, 1327.)(c) Dai, H.; Miao, W.-K.; Liu, J.-B.; Wu, S.-S.; Qin, X.; Fang, J.-X. Chin. J. Org. Chem. 2012, 32, 1690 (in Chinese).(戴红, 苗文科, 刘建兵, 吴珊珊, 秦雪, 方建新, 有机化学, 2012, 32, 1690.)(d) Huang, G.; Yang, J. C.; Li, H.-C.; Zhang, J.; Liu, C.-L. Pesticides 2011, 50, 79 (in Chinese).(黄光, 杨吉春, 李慧超, 张静, 刘长令, 农药, 2011, 50, 79.)
[6] Li, N.; Wei, X.; Fan, H.-T.; Bi, L.; Li, X.-Y.; Yang, S.; Hu, D. Y.; Song, B. A. Chin. J. Org. Chem. 2011, 31, 1300 (in Chinese).(李娜, 魏学, 范会涛, 毕亮, 李向阳, 杨松, 胡德禹, 宋宝安, 有机化学, 2011, 31, 1300.)
[7] Liu, L.; Zheng, Z.-B.; Qin, Z.-H.; Fu, B.; Yuan, H.-Z. Chin. J. Org. Chem. 2008, 28, 1841 (in Chinese).(刘磊, 郑中博, 覃兆海, 傅滨, 袁会珠, 有机化学, 2008, 28, 1841.)
[8] (a) Fu, B.; Qi, Q.-Q.; Lu, X.-H.; Cheng, X.-M.; Xiao, Y.-M.; Li, N. Chin. J. Org. Chem. 2008, 28, 1358 (in Chinese).(傅滨, 齐卿卿, 路绪红, 程学明, 肖玉梅, 李楠, 有机化学, 2008, 28, 1358.)(b) Lu, X.-H.; Qi, Q.-Q.; Xiao, Y. M.; Li, N.; Fu, B. Heterocycles2009, 79, 1031.
[9] Chen, N.-C. Bioassay of Pesticides, Beijing Agricultural University Press, Beijing, 1991, p. 161 (in Chinese).(陈年春, 农药生物测定技术, 北京农业大学出版社, 北京, 1991, p. 161.)
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