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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Xiao Tingting , Cheng Wei , Qian Weifeng , Zhang Tingting , Lu Tong , Gao Yang , Tang Xiaorong . Synthesis of Chalcone Derivatives and Studies on Their Inhibitory Activity and Molecular Docking[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1704 -1715 . DOI: 10.6023/cjoc201911034

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