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Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives.

Lu XuJinmeng YuLu JinLe Pan
Published in: Molecules (Basel, Switzerland) (2022)
A series of 30 succinate dehydrogenase inhibitors (SDHIs) of 4-amino coumarin-based derivatives were designed and synthesized. According to the analysis of fungicidal activity in vitro, most of the compounds expressed broad-spectrum antifungal activity against four plant pathogenic fungi ( Alternaria alternata, Alternaria solani, Fusarium oxysporum, and Botrytis cinerea ) using the mycelium growth inhibition method. The results showed that compounds 3n with the group of 2-ene-3-methyl-butyl and 4e with the group of 2-bromo-1-oxo-hexyl displayed excellent activity against Alternaria alternata and Alternaria solani , with EC 50 values of 92~145 μg/mL. Molecular docking showed that the inhibitor 3n was completely locked into the cavity of SDH, forming a conventional hydrogen bond interacting with the amino acid residue TYR58. The present work indicates that these derivatives would serve as novel potential fungicides targeting SDH.
Keyphrases
  • molecular docking
  • amino acid
  • structure activity relationship
  • molecular dynamics simulations
  • fluorescent probe
  • risk assessment
  • human health