Citation: 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 shu

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

School of Science, Xihua University, Chengdu 610039

Corresponding author: Tang Xiaorong, tangxr112@126.com
Received Date: 26 November 2019
Revised Date: 11 January 2020
Available Online: 23 February 2020
Fund Project: the Innovation Fund of Postgraduate of Xihua University YCJJ2019025Project 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)the Undergraduate Innovation and Entrepreneurship Training Programs of Xihua University 201810623009the Technical Innovation Programs of Chengdu Municipal Bureau of Science and Technology 2018-YF05-00970-SN

Figures(6)

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.
- antifungal activity,
- chalcone derivatives,
- molecular docking,
- succinate dehydrogenase inhibitor
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