含芳硫醚结构的新型酰胺衍生物的设计、合成和生物活性
收稿日期: 2019-03-03
修回日期: 2019-03-31
网络出版日期: 2019-04-19
基金资助
山东省自然科学基金（No.ZR2017BC053）、聊城大学博士科研启动基金（No.318051625）、聊城大学大学生创新创业训练（No.CXCY2018181）资助项目.
Design, Synthesis and Biological Activity Screening of Novel Amide Derivatives Containing Aromatic Thioether Group
Received date: 2019-03-03
Revised date: 2019-03-31
Online published: 2019-04-19
Supported by
Project supported by the Natural Science Foundation of Shandong Province (No. ZR2017BC053), the Doctoral Research Startup Foundation of Liaocheng University (No. 318051625), and the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University (No. CXCY2018181).
华学文 , 刘南南 , 范志金 , 宗广宁 , 马翼 , 雷康 , 殷昊 , 王桂清 . 含芳硫醚结构的新型酰胺衍生物的设计、合成和生物活性[J]. 有机化学, 2019 , 39(9) : 2581 -2588 . DOI: 10.6023/cjoc201903004
A series of amide derivatives containing aromatic sulfide and sulfone groups synthesized in our previous work displayed excellent nematocidal activity at 200 μg/mL. In order to explore the effect of structural modification of the amide bridge on biological activity in a more delicate way, two series of novel target compounds were designed and synthesized by adopting amide group flipping and introducing N-sulfonyl substituted amide bonds. The bioassays indicated that the structural modification of the amide bridge had important effects on their nematocidal and fungicidal activities, which the introduction of the N-sulfonyl substituent on the amide group was favorable to improving the nematocidal activity in comparison with compounds I. The molecular docking revealed that directly attaching the carbonyl or sulfonyl groups in the amide bridge to the aromatic rings was advantageous to the nematocidal activity.
Key words： synthesis; thioether; amide; nematocidal activity; molecular docking
[1] Lu, H. B.; Xu, S. Y.; Zhang, W. J.; Xu, C. M.; Li, B. X.; Zhang, D. X.; Mu, W.; Liu, F. J. Agric. Food Chem. 2017, 65, 544.
[2] Al-Idrus, A.; Carpentier, S. C.; Ahmad, M. T.; Panis, B.; Mohamed, Z. PLoS One 2017, 12, e0178438/1.
[3] Kearn, J.; Ludlow, E.; Dillon, J.; O'Connor, V.; Holden-Dye, L. Pestic. Biochem. Phys. 2014, 109, 44.
[4] Cheng, L.; Xu, S. Y.; Xu, C. M.; Lu, H. B.; Zhang, Z. Q.; Zhang, D. X.; Mu, W.; Liu, F. Pest Manage. Sci. 2017, 73, 888.
[5] Lahm, G. P.; Desaeger, J.; Smith, B. K.; Pahutski, T. F.; Rivera, M. A.; Meloro, T.; Kucharczyka, R.; Lett, R. M.; Daly, A.; Smith, B. T.; Cordova, D.; Thoden, T.; Wiles, J. A. Bioorg. Med. Chem. Lett. 2017, 27, 1572.
[6] Hungenberg, H.; Fürsch, H.; Rieck, H.; Hellwege, E. US 20130253018, 2013.
[7] Raymond, R. G.; Gray, R. M. WO 2017013083, 2017.
[8] Slomczynska, U.; South, M. S.; Bunkers, G. J.; Edgecomb, D.; Wyse-Pester, D.; Selness, S.; Ding, Y.; Christiansen, J.; Ediger, K.; Miller, W.; Charumilind, P.; Hartmann, G.; Williams, J.; Dimmic, M.; Shortt, B.; Haakenson, W.; Wideman, A.; Crawford, M.; Hresko, M.; McCarter, J. ACS Sym. Ser. 2015, 1204, 129.
[9] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[10] Zhao, W.; Shen, Z. H.; Xing, J. H.; Yang, G.; Xu, T. M.; Peng, W. L.; Liu, X. H. Chem. Pap. 2017, 71, 921.
[11] Lahm, G. P.; Deangelis, A. J.; Campbell, M. J. WO 2017116646, 2017.
[12] El Qacemi, M.; Bigot, A.; Edmunds, A.; Gagnepain, J. D. H.; Jeanguenat, A.; Pitterna, T.; Stoller, A.; Sabbadin, D. WO 2017055414, 2017.
[13] Jeanguenat, A.; Pitterna, T.; El Qacemi, M.; Stoller, A.; Mondiere, R. J. G.; Bigot, A.; Edmunds, A.; Gribkov, D. WO 2017140771, 2017.
[14] Yoneda, T.; Yoshida, K.; Tazawa, Y.; Kani, T.; Cho, Y.; Noujima, A.; Murai, Y. WO 2017222037, 2017.
[15] Müller, K. H.; Kübbeler, S.; Greul, J.; Portz, D.; Malsam, O.; Ilg, K. WO 2015169776, 2015.
[16] Hua, X. W.; Liu, N. N.; Yin, H.; Zhang, C.; Zhang, N.; Zhang, Y. J. Liaocheng Univ. (Nat. Sci. Ed.) 2018, 31, 60(in Chinese). (华学文, 刘南南, 殷昊, 张晨, 张娜, 张媛, 聊城大学学报(自然科学版), 2018, 31, 60.)
[17] Song, B. A.; Chen, X. W.; Chen, Y. Z.; Hu, D. Y.; Xue, W.; Chen, J. X.; Wang, Y. L.; Wang, Z. Z. CN 105646393, 2016.
[18] Liu, G.; Lai, D. W.; Liu, Q. Z.; Zhou, L. G.; Liu, Z. L. Molecules 2016, 21, 1276.
[19] Liu, Y.; Liu, M.; Chen, M. G.; Wu, C. C.; Hua, X. W.; Zhou, S.; Wang, B. L.; Li, Z. M. Chin. J. Org. Chem. 2017, 37, 403(in Chinese). (刘阳, 刘明, 陈明桂, 吴长春, 华学文, 周莎, 王宝雷, 李正名, 有机化学, 2017, 37, 403.)
[20] Faske, T. R.; Hurd, K. J. Nematol. 2015, 47, 316.
[21] Jain, A. N. J. Med. Chem. 2003, 46, 499.
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