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2020 , Vol. 40 >Issue 6: 1704 - 1715

DOI: https://doi.org/10.6023/cjoc201911034

研究论文

查尔酮衍生物的合成及其抑菌活性和分子对接研究

  • 肖婷婷 ,
  • 程玮 ,
  • 钱伟烽 ,
  • 张婷婷 ,
  • 陆童 ,
  • 高扬 ,
  • 唐孝荣
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  • 西华大学理学院 成都 610039

收稿日期: 2019-11-26

  修回日期: 2020-01-11

  网络出版日期: 2020-03-04

基金资助

成都市科学技术局技术创新（No.2018-YF05-00970-SN）、西华大学研究生创新基金（No.YCJJ2019025）和西华大学大学生创新创业训练计划（No.201810623009）资助项目.

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Synthesis of Chalcone Derivatives and Studies on Their Inhibitory Activity and Molecular Docking

  • Xiao Tingting ,
  • Cheng Wei ,
  • Qian Weifeng ,
  • Zhang Tingting ,
  • Lu Tong ,
  • Gao Yang ,
  • Tang Xiaorong
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  • School of Science, Xihua University, Chengdu 610039

Received date: 2019-11-26

  Revised date: 2020-01-11

  Online published: 2020-03-04

Supported by

Project supported by the Technical Innovation Programs of Chengdu Municipal Bureau of Science and Technology (No. 2018-YF05-00970-SN), the Innovation Fund of Postgraduate of Xihua University (No. YCJJ2019025) and the Undergraduate Innovation and Entrepreneurship Training Programs of Xihua University (No. 201810623009).

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摘要

设计合成了29个查尔酮衍生物，并用IR、1H NMR、13C NMR和HRMS对其结构进行了表征.测定了所有合成化合物对5种植物病原真菌即水稻纹枯病原真菌、小麦赤霉病原真菌、玉米小斑病原真菌、油菜菌核病原真菌和番茄灰霉病原真菌的抑菌活性.初步的结果显示，大多数化合物都有显著的抑菌活性，其中，（E）-N-（4-（3-（5-溴噻吩-2-基）丙烯酰基）苯基）烟酰胺（4m）（EC50=0.057 mg/L）和（E）-2-羟基-N-（4-（3-（吡啶-3-基）丙烯酰基）苯基）乙酰胺（6i）（EC50=0.054 mg/L）对油菜菌核表现出最强的抑制活性，活性优于市售杀菌剂氟吡菌酰胺（EC50=0.244 mg/L）.与此同时，还测定了化合物4m和6i对琥珀酸脱氢酶（SDH）的抑制活性.结果显示，它们都比氟吡菌酰胺有更好的抑制活性.分子对接研究表明，化合物4m和6i都与SDH结合得很好，结合能分别为-31.0和-31.4 kJ/mol.而且，化合物4m和6i分别与SDH的B/Trp-230残基形成了一个氢键.

关键词： 抑菌活性; 查尔酮衍生物; 分子对接; 琥珀酸脱氢酶抑制剂

本文引用格式

肖婷婷 , 程玮 , 钱伟烽 , 张婷婷 , 陆童 , 高扬 , 唐孝荣 . 查尔酮衍生物的合成及其抑菌活性和分子对接研究[J]. 有机化学, 2020 , 40(6) : 1704 -1715 . DOI: 10.6023/cjoc201911034

Abstract

Twenty nine chalcone derivatives were designed, synthesized and characterized by IR, 1H NMR, 13C NMR and HRMS. The antifungal activities of all the synthesized compounds were determined against five plant pathogenic fungi namely Rhizoctonia solani, Fusarum graminearum, Helminthosporium maydis, Sclerotinia sclerotiorum and Botrytis cinerea. Preliminary results indicated that most of them revealed significant antifungal activity. Among them, (E)-N-(4-(3-(5-bromothiophen-2-yl)acryloyl)phenyl)nicotinamide (4m) (EC50=0.057 mg/L) and (E)-2-hydroxy-N-(4-(3-(pyridin-3-yl)acryloyl)phenyl)ace-tamide (6i) (EC50=0.054 mg/L) showed the strongest activities against S. sclerotiorum and possessed better antifungal activities than the commercial fungicide of fluopyram (EC50=0.244 mg/L). Meanwhile, the inhibitory activities of compounds 4m and 6i were tested against succinate dehydrogenase (SDH). The results displayed that they had also better activities than fluopyram. Molecular docking studies demonstrated that compounds 4m and 6i bound well to SDH and their binding energies were -31.0 and -31.4 kJ/mol, respectively. Moreover, compounds 4m and 6i formed hydrogen bonds with residue B/Trp-230 of SDH, respectively.

Key words： antifungal activity; chalcone derivatives; molecular docking; succinate dehydrogenase inhibitor

参考文献

[1] Chen, Y.; Zhang, A. F.; Wang, W. X.; Zhang, Y.; Gao, T. C. Ann. Appl. Biol. 2012, 161, 247.
[2] Yanase, Y.; Kishi, J.; Inami, S.; Katsuta, H.; Yoshikawa, Y. J. Pestic. Sci. 2013, 38(4), 188.
[3] Veloukas, T.; Karaoglanidis, G. S. Pest Manage. Sci. 2012, 68(6), 858.
[4] Xiong, L.; Shen, Y. Q., Jiang, L. N.; Zhu, X. L.; Yang, W. C.; Huang, W.; Yang, G. F. ACS Symp. Ser. 2015, 1204, 175.
[5] Xiong, L.; Li, H.; Jiang, L. N.; Ge, J. M.; Yang, W. C.; Zhu, X. L.; Yang, G. F. J. Agric. Food. Chem. 2017, 65, 1021.
[6] Jin, H.; Zhou, J. Y.; Pu, T.; Zhang, A. G.; Gao, X. H.; Tao, K.; Hou, T. P. Bioorg. Chem. 2017, 73, 76.
[7] Yao, T. T.; Xiao, D. X.; Li, Z. S.; Cheng, J. L.; Fang, S. W.; Du, Y. J.; Zhao, J. H.; Dong, X. W.; Zhu, G. N. J. Agric. Food Chem. 2017, 65, 5397.
[8] Yao, T. T.; Fang, S. W.; Li, Z. S.; Xiao, D. X.; Cheng, J. L.; Ying, H. Z.; Du, Y. J.; Zhao, J. H.; Dong, X. W. J. Agric. Food Chem. 2017, 65, 3204.
[9] Zhang, X. X.; Jin, H.; Deng, Y. J.; Gao, X. H.; Li, Y.; Zhao, Y. T.; Tao, K.; Hou, T. P. Chin. Chem. Lett. 2017, 28, 1731.
[10] Wang, H. Y.; Gao, X. H.; Zhang, X. X.; Jin, H.; Tao, K.; Hou, T. P. Med. Chem. Lett. 2017, 27, 90.
[11] Zhang, A. G.; Zhou, J. Y.; Tao, K.; Hou, T. P.; Jin, H. Bioorg. Med. Chem. Lett. 2018, 28, 3042.
[12] Zhang, A. G.; Yue, Y.; Yang, Y. H.; Yang, J.; Tao, K.; Jin, H.; Hou, T. P. Pestic. Biochem. Phys. 2019, 158, 175.
[13] Sivakumar, P. M.; Ganesan, S.; Veluchamy, P.; Doble, M. Chem. Biol. Drug Des. 2010, 76, 407.
[14] Bandgar, B. P.; Patil, S. A.; Korbad, B. L.; Nile, S. H.; Khobragade, C. N. Eur. J. Med. Chem. 2010, 45, 2629.
[15] Rane, R. A.; Telvekar, V. N. Bioorg. Med. Chem. Lett. 2010, 20, 5681.
[16] Solankee, A.; Kapadia, K.; Ćirić, A.; Soković, M.; Doytchinova, I.; Geronikaki, A. Eur. J. Med. Chem. 2010, 45, 510.
[17] De Carvalho Tavares, L.; Johann, S.; De Almeida Alves, T. M.; Guerra, J. C.; De Souza-Fagundes, E. M.; Cisalpino, P. S.; Bortoluzzi, A. J.; Caramori, G. F.; De Mattos Piccoli, R.; Braibante, H. T. S.; Braibante, M. E. F.; Pizzolatti, M. G. Eur. J. Med. Chem. 2011, 46, 4448.
[18] Sugamoto, K.; Matsusita, Y.; Matsui, K.; Kurogi, C.; Matsui, T. Tetrahedron 2011, 67, 5346.
[19] Chu, W. C.; Bai, P. Y.; Yang, Z. Q.; Cui, D. Y.; Hua, Y. G.; Yang, Y.; Yang, Q. Q.; Zhang, E.; Qin, S. S. Eur. J. Med. Chem. 2018, 143, 905.
[20] Zhou, D. G.; Xie, D. D.; He, F. C.; Song, B. A.; Hu, D. Y. Bioorg. Med. Chem. Lett. 2018, 28, 2091.
[21] Tomar, V.; Bhattacharjee, G.; Kamaluddin; Rajakumar, S.; Srivastava, K.; Puri, S. K. Eur. J. Med. Chem. 2010, 45, 745.
[22] Wanare, G.; Aher, R.; Kawathekar, N.; Ranjan, R.; Kaushik, N. K.; Sahal, D. Bioorg. Med. Chem. Lett. 2010, 20, 4675.
[23] Nazarian, Z.; Emami, S.; Heydari, S.; Ardestani, S. K.; Nakhjiri, M.; Poorrajab, F.; Shafiee, A.; Foroumadi, A. Eur. J. Med. Chem. 2010, 45, 1424.
[24] Sharath, V.; Kumar, H. V.; Naik, N. J. Pharm. Res. 2013, 6, 785.
[25] El Sayed Aly, M. R.; El Razek Fodah, H. H. A.; Saleh, S. Y. Eur. J. Med. Chem. 2014, 76, 517.
[26] Fu, Y.; Sheng, L.; Gao, L.; Li, J.; Sun, L. Chin. J. Org. Chem. 2019, 39, 1029(in Chinese). (付洋, 盛丽, 高立信, 李佳, 孙良鹏, 有机化学, 2019, 39, 1029.)
[27] Pontes, O.; Costa, M.; Santos, F.; Sampaio-Marques, B.; Dias, T.; Ludovico, P.; Baltazar, F.; Proença, F. Eur. J. Med. Chem. 2018, 157, 101.
[28] Sheng, Q.; Zhao, W. Q.; Zeng, M.; Xie, Z. P.; Xia, Y. P.; Cui, D. M. Chin. J. Org. Chem. 2019, 39, 703(in Chinese). (盛琦威, 赵婉秋, 曾明, 谢中袍, 夏雅平, 崔冬梅, 有机化学, 2019, 39(3), 703.)
[29] Bano, S.; Javed, K.; Ahmad, S.; Rathish, I. G.; Singh, S.; Chaitanya, M.; Arunasree, K. M.; Alam, M. S. Eur. J. Med. Chem. 2013, 65, 51.
[30] Lin, Y. M.; Zhou, Y.; Flavin, M. T.; Zhou, L. M.; Nie, W.; Chen, F. C. Bioorg. Med. Chem. 2002, 10, 2795.
[31] Ono, M.; Hori, M.; Haratake, M.; Tomiyama, T.; Mori, H.; Nakayama, M. Bioorg. Med. Chem. 2007, 15, 6388.
[32] Dos Santos, M. B.; Bertholin Anselmo, D.; De Oliveira, J. G.; Jardim-Perassi, B. V.; Alves Monteiro, D.; Silva, G.; Gomes, E.; Lucia Fachin, A.; Marins, M.; De Campos Zuccari, D. A. P.; Octavio Regasini, L. J. Enzyme Inhib. Med. Chem. 2019, 34, 1093.
[33] Karaman, I.; Gezegen, H.; Gürdere, M. B.; Dingil, A.; Ceylan, M. Chem. Biodiversity 2010, 7, 400.
[34] Zhu, M.; Wang, J.; Xie, J. B.; Chen, L. P.; Wei, X. Y.; Jiang, X.; Bao, M.; Qiu, Y. Y.; Chen, Q.; Li, W. L.; Jiang, C. X.; Zhou, X. O.; Jiang, L. P.; Qiu, P. H.; Wu, J. Z. Eur. J. Med. Chem. 2018, 157, 1395.
[35] Chu, W. C.; Bai, P. Y.; Yang, Z. Q.; Cui, D. Y.; Hua, Y. G.; Yang, Y.; Yang, Q, Q.; Zhang, E.; Qin, S. S. Eur. J. Med. Chem. 2017, 143, 905.
[36] Ye, Y. H.; Ma, L.; Dai, Z. C.; Xiao, Y.; Zhang, Y. Y.; Li, D. D.; Wang, J. X.; Zhu, H. L. J. Agric. Food Chem. 2014, 62, 4063.
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