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


时艳华, 张帅, 万福贤, 孙昌兴, 姜林   

  1. 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
  • 基金资助:

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   

  1. 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).

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