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

doi:10.6023/cjoc201911034

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1704-1715.DOI: 10.6023/cjoc201911034 Previous Articles Next Articles

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

西华大学理学院成都 610039

收稿日期:2019-11-26 修回日期:2020-01-11 发布日期:2020-03-04
通讯作者: 唐孝荣 E-mail:tangxr112@126.com
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.

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

School of Science, Xihua University, Chengdu 610039

Received:2019-11-26 Revised:2020-01-11 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).

1. 201704S.pdf(8674KB)

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

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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.

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查尔酮衍生物的合成及其抑菌活性和分子对接研究

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

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