Synthesis and evaluation of imidazo[1,2-a]quinoxaline derivatives as potential antifungal agents against phytopathogenic fungi

Ma, Taigui; Zhong, Xu; Yang, Ya; Liu, Wenjing; Guo, Bing; Fan, Judi; Tang, Lei; Fan, Lingling; Li, Yong

doi:10.1007/s11030-023-10739-y

Cited by 3 publications

(2 citation statements)

References 21 publications

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“…Effects of compound 5 b on the spore germination [22] Considering the inhibition of spore germination and germ tube elongation is an important means to control fungi diseases, light microscopy was used to study the effects of compound 5 b on the spore germination and germ tube growth of V. mali at three different concentrations (Figure 3). The data of this experiment indicated that compound 5 b could markedly suppress the spore germination in a dose-dependent manner compared with the blank control group, and the inhibition rates at concentrations of 2.5, 5.0, 10.0 μg/mL are 53.7 %, 80.5 %, 100 %, respectively, which was comparable to the positive control chlorothalonil.…”

Section: In Vitro Antifungal Activitymentioning

confidence: 99%

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Design and Synthesis of Novel Phthalide Derivatives containing 1,3,4‐Oxadiazole/1,2,4‐Triazole Units as Potential Antifungal Agents

Li,

Luo,

Liu

et al. 2024

Chemistry & Biodiversity

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Four series of novel 1,3,4‐oxadiazole/1,2,4‐triazole hybrids of phthalide derivatives were designed and synthesized to search for novel potential antifungal agents. Preliminary antifungal activity assay results showed that compounds 4a, 4b, 4m, 5b, 5f, 5h, and 7h exhibited moderate to excellent inhibitory activity against some phytopathogenic fungi. Among them, compound 5b displayed the most outstanding antifungal effects against V. mali and S. sclerotiorum, with the EC50 mean of 3.96 μg/mL and 5.60 μg/mL, respectively, which was superior to those of commercial fungicides hymexazol and chlorothalonil. Furthermore, compound 5b could completely suppress the spore germination of V. mali at a concentration of 10 μg/mL. Finally, molecular docking revealed that the potential target for the antifungal activity of compound 5b was succinate dehydrogenase (SDH). This research provides novel candidate compounds for the prevention of phytopathogenic fungi.

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Section: In Vitro Antifungal Activitymentioning

confidence: 99%

“…The antifungal activity and spore germination of the compounds were evaluated according to the standard operating methods reported in our previous work. [5,22] (Supporting Information)…”

Section: Biological Activitymentioning

confidence: 99%

Design and Synthesis of Novel Phthalide Derivatives containing 1,3,4‐Oxadiazole/1,2,4‐Triazole Units as Potential Antifungal Agents

Li,

Luo,

Liu

et al. 2024

Chemistry & Biodiversity

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Design and synthesis of some novel structurally diverse thiochroman derivatives as fungicides against phytopathogenic fungi

Liu,

Li,

Liang

et al. 2024

Pest Management Science

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BACKGROUNDPlant diseases infected by pathogenic fungi have a devastating effect on global agricultural and food industry yields. The development of novel, environmentally friendly, and efficient fungicides is an important technique for preventing and combatting phytopathogenic fungi.RESULTSHerein, 99 thiochroman‐based derivatives containing hydroxyl, sulfoxide, sulfone, carbonyl, double bond, amino, imine, oxime, oxime ester, and amide moieties were synthesized. The antifungal activities of the target compounds against ten typical phytopathogenic fungi were also investigated. The bioassay results illustrated that most of the target compounds exhibited moderate to excellent antifungal effects against the tested fungi in vitro. Among these, thiochroman‐oxime derivatives (12a–12m) exerted a promising inhibition effect, especially against Fusarium solani, Fusarium graminearum, Valsa mali, and Botrytis cinerea strains. Furthermore, the compounds 12f and 12g markedly suppressed the spore germination germ and tube growth. At the same time, they exerted excellent protective effects against potatoes infected by F. solani, making them superior to commercial fungicides Hymexazol and Chlorothalonil. Notably, the compounds 12d and 12f also showed excellent protective effects against cherry tomatoes infected by B. cinerea. Further mechanistic studies revealed that compound 12f exerted an antifungal effect by overtly altering the mycelium structure and remarkably increasing cell membrane permeability. Fortunately, the excellent bioactive compounds showed good safety against human hepatic cell lines (WRL‐68). The preliminary structure–activity relationship analysis revealed that the introduction of hydroxyl or oxime fragments at the thiopyran ring might be significantly beneficial to antifungal activity.CONCLUSIONThis study provides thiochroman compounds that can be used in the development of novel botanical fungicides for the management of phytopathogenic fungi. © 2024 Society of Chemical Industry.

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Synthesis and antifungal activities of small molecule arylthiazolamine derivatives

Zhong,

He,

et al. 2024

Mol Divers

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Synthesis and evaluation of imidazo[1,2-a]quinoxaline derivatives as potential antifungal agents against phytopathogenic fungi

Cited by 3 publications

References 21 publications

Design and Synthesis of Novel Phthalide Derivatives containing 1,3,4‐Oxadiazole/1,2,4‐Triazole Units as Potential Antifungal Agents

Design and Synthesis of Novel Phthalide Derivatives containing 1,3,4‐Oxadiazole/1,2,4‐Triazole Units as Potential Antifungal Agents

Design and synthesis of some novel structurally diverse thiochroman derivatives as fungicides against phytopathogenic fungi

Synthesis and antifungal activities of small molecule arylthiazolamine derivatives

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