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. 2025 Aug 20.
doi: 10.1007/s11030-025-11317-0. Online ahead of print.

Design, synthesis, and mechanism study of novel isoquinoline derivatives containing an oxime moiety as antifungal agents

Yanxi Jin  1 , Fu Chen  1 , Ying Long  1 , Jianeng Luo  1 , Si Guo  1 , LuYao Wang  1 , Wei Chen  2
Affiliations

Design, synthesis, and mechanism study of novel isoquinoline derivatives containing an oxime moiety as antifungal agents

Yanxi Jin et al. Mol Divers. .

Abstract

A series of novel isoquinoline derivatives 5a-5 s incorporating bioactive amide and oxime ester moieties were rationally designed and synthesized based-on isoquinoline alkaloid scaffolds through pharmacophore splicing strategy. Their structures were verified by 1H NMR, 13C NMR, IR and HRMS. The fungicidal bioassay indicated that most of the target compounds showed good to excellent inhibitory activity against five phytopathogenic fungi in vitro at a concentration of 50 mg/L. Notably, compounds 5 l and 5q exhibited excellent fungicidal activity against S. sclerotiorum with EC50 values reached 8.27 and 8.18 mg/L, respectively, which were comparable to boscalid (8.03 mg/L). 5q exhibited 100% protective and 73.87% curative efficacy against S. sclerotiorum on Brassica napus L. leaves at 100 mg/L. Particularly, compound 5q exhibits potent inhibitory effect against Succinate dehydrogenase (SDH) of S. sclerotiorum with IC50 of 5.05 uΜ. Furthermore, SDH activity assays and molecular docking analyses demonstrated that 5q can interact with SDH in a variety of ways. These results provide substantial insight for the development of novel natural-derived isoquinoline derivatives as potential antifungal agents.

Keywords: Antifungal activity; Antifungal mechanism; Isoquinoline derivatives; Oxime moiety.

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Conflict of interest statement

Declarations. Conflict of interest: The authors declare no competing interests.

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References

    1. Peng F, Tai L, Zhang A et al (2025) Novel naphthyl and phenyl maleimide derivatives: molecular design, systematic optimization, antifungal evaluation, and action mechanism. J Agric Food Chem 73:12026–12037. https://doi.org/10.1021/acs.jafc.5c00920 - DOI - PubMed
    1. Jain A, Surendra S, Qin W et al (2019) A review of plant leaf fungal diseases and its environment speciation. Bioengineered 10:409–424. https://doi.org/10.1080/21655979.2019.1649520 - DOI - PubMed - PMC
    1. Zhang YH, Yang SS, Zhang Q et al (2023) Discovery of N-phenylpropiolamide as a novel succinate dehydrogenase inhibitor scaffold with broad-spectrum antifungal activity on phytopathogenic fungi. J Agric Food Chem 71:3681–3693. https://doi.org/10.1021/acs.jafc.2c07712 - DOI - PubMed
    1. Zhang L, Chen Y, Wu W et al (2025) Design, synthesis, and bioactivity evaluation of novel indene amino acid derivatives as succinate dehydrogenase inhibitors. J Agric Food Chem 73:10130–10143. https://doi.org/10.1021/acs.jafc.5c00009 - DOI - PubMed
    1. Zhong LK, Sun XP, Han L et al (2023) Design, synthesis, insecticidal activity, and SAR of aryl isoxazoline derivatives containing pyrazole-5-carboxamide motif. J Agric Food Chem 71:14458–14470. https://doi.org/10.1021/acs.jafc.3c01608 - DOI - PubMed

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