Synthesis, Fungicidal Activity and Molecular Docking Study of Novel N-[2-((Substitutedphenyl)amino)pyridin-3-yl]-pyrimidine-4-carboxamides

doi:10.6023/cjoc202002019

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 1948-1954.DOI: 10.6023/cjoc202002019 Previous Articles Next Articles

新型N-[2-((取代苯基)氨基)吡啶-3-基]嘧啶甲酰胺的合成、杀菌活性及分子对接

时艳华, 张帅, 万福贤, 孙昌兴, 姜林

山东农业大学化学与材料科学学院山东泰安 271018

收稿日期:2020-02-17 修回日期:2020-03-15 发布日期:2020-04-10
通讯作者: 姜林 E-mail:jiangl@sdau.edu.cn
基金资助:
山东省自然科学基金（No.ZR2014BM030）资助项目.

Synthesis, Fungicidal Activity and Molecular Docking Study of Novel N-[2-((Substitutedphenyl)amino)pyridin-3-yl]-pyrimidine-4-carboxamides

Shi Yanhua, Zhang Shuai, Wan Fuxian, Sun Changxing, Jiang Lin

College of Chemistry and Material Science, Shandong Agricultural University, Tai'an, Shandong 271018

Received:2020-02-17 Revised:2020-03-15 Published:2020-04-10
Supported by:
Project supported by the Natural Science Foundation of Shandong Province (No. ZR2014BM030).

1. 201948S.pdf(3746KB)

Abstract

To explore succinate dehydrogenase inhibitor with new structure, the excellent fungicide boscalid was chosen as a lead compound, and seventeen N-[2-((substitutedphenyl)amino)pyridin-3-yl]-4-methyl-2-(methylthio)pyrimidine-5-carbox-amides (4a~4g) and N-[2-((substitutedphenyl)amino)pyridin-3-yl]-4-methoxy-2-(methylthio)pyrimidine-5-carboxamides (4h~4q) were designed and synthesized. The structures of target compounds were characterized by ¹H NMR, ¹³C NMR, and MALDI-TOF-MS. The in vitro bioassay showed that sixteen compounds possessed high fungicidal activity against S. sclerotiorum with more than 90% inhibitory rate at 50 μg/mL, and some compounds showed moderate activity against B. cinerea at the same dose with inhibitory rate in the range of 70%~84%. The molecular docking study revealed that four hydrogen bonds and one cation-π interaction were formed between N-[2-((3-fluoro-4-methylphenyl)amino)pyridin-3-yl]-4-methoxy-2-(methyl-thio)pyrimidine-5-carboxamide (4p) and succinate dehydrogenase (SDH) enzyme.

Key words: pyrimidine, carboxamide, synthesis, fungicidal activity, molecular docking

Cite this article

Shi Yanhua, Zhang Shuai, Wan Fuxian, Sun Changxing, Jiang Lin. Synthesis, Fungicidal Activity and Molecular Docking Study of Novel N-[2-((Substitutedphenyl)amino)pyridin-3-yl]-pyrimidine-4-carboxamides[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1948-1954.

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新型N-[2-((取代苯基)氨基)吡啶-3-基]嘧啶甲酰胺的合成、杀菌活性及分子对接

Synthesis, Fungicidal Activity and Molecular Docking Study of Novel N-[2-((Substitutedphenyl)amino)pyridin-3-yl]-pyrimidine-4-carboxamides

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