Computation-Directed Molecular Design, Synthesis, and Fungicidal Activity of Succinate Dehydrogenase Inhibitors

Li, Kun; Hong, Shuang; Yu, Zhenwu; Hong, Zeyu; Sun, Yaru; Cheng, Jiagao; Tang, Liangfu; Wang, Yong; Qi, Xin; Fan, Zhijin

doi:10.1021/acs.jafc.3c05232

Cited by 2 publications

(2 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To further explore the potential fungicidal ability of active compounds, a median effective concentration (EC 50 ) value test was carried out according to the established method. The statistical analyses were performed by SPSS software version 26.0 …”

Section: Methodsmentioning

confidence: 99%

Fungicidal Activity of New Pyrrolo[2,3-d]thiazoles and Their Potential Action on the Tryptophan Metabolic Pathway and Wax Biosynthesis

Zhang,

Li,

Yang

et al. 2024

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

The main challenge in the development of agrochemicals is the lack of new leads and/or targets. It is critical to discover new molecular targets and their corresponding ligands. YZK-C22, which contains a 1,2,3-thiadiazol-[1,2,4]triazolo [3,4b][1,3,4]thiadiazole skeleton, is a fungicide lead compound with broad-spectrum fungicidal activity. Previous studies suggested that the [1,2,4]triazolo [3,4-b][1,3,4]thiadiazole scaffold exhibited good antifungal activity. Inspired by this, a series of pyrrolo[2,3d]thiazole derivatives were designed and synthesized through a bioisosteric strategy. Compounds C1, C9, and C20 were found to be more active against Rhizoctonia solani than the positive control YZK-C22. More than half of the target compounds provided favorable activity against Botrytis cinerea, where the EC 50 values of compounds C4, C6, C8, C10, and C20 varied from 1.17 to 1.77 μg/mL. Surface plasmon resonance and molecular docking suggested that in vitro potent compounds C9 and C20 have a new mode of action instead of acting as pyruvate kinase inhibitors. Transcriptome analysis revealed that compound C20 can impact the tryptophan metabolic pathway, cutin, suberin, and wax biosynthesis of B. cinerea. Overall, pyrrolo[2,thiazole is discovered as a new fungicidal lead structure with a potential new mode of action for further exploration.

show abstract

Section: Methodsmentioning

confidence: 99%

Fungicidal Activity of New Pyrrolo[2,3-d]thiazoles and Their Potential Action on the Tryptophan Metabolic Pathway and Wax Biosynthesis

Zhang,

Li,

Yang

et al. 2024

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…In a study conducted by Li and colleagues, molecular docking and 3D-QSAR models were used on 33 pyrazole-containing compounds and their activity against R. cerealis was evaluated . Using comparative molecular field analysis and comparative molecular similarity indices analysis, the structure–activity relationships were studied.…”

Section: Review Backgroundmentioning

confidence: 99%

Recent Advances in Design and Development of Diazole and Diazine Based Fungicides (2014–2023)

Saeedian Moghadam,

Bonyasi,

Bayati

et al. 2024

J. Agric. Food Chem.

View full text Add to dashboard Cite

With fungal diseases posing a major threat to agricultural production, the application of fungicides to control related diseases is often considered necessary to ensure the world's food supply. The search for new bioactive agents has long been a priority in crop protection due to the continuous development of resistance against currently used types of active compounds. Heterocyclic compounds are an inseparable part of the core structures of numerous lead compounds, these rings constitute pharmacophores of a significant number of fungicides developed over the past decade by agrochemists. Among heterocycles, nitrogen-based compounds play an essential role. To date, diazole (imidazole and pyrazole) and diazine (pyrimidine, pyridazine, and pyrazine) derivatives make up an important series of synthetic fungicides. In recent years, many reports have been published on the design, synthesis, and study of the fungicidal activity of these scaffolds, but there was a lack of a comprehensive classified review on nitrogen-containing scaffolds. Regarding this issue, here we have reviewed the published articles on the fungicidal activity of the diazole and diazine families. In current review, we have classified the molecules synthesized so far based on the size of the ring.

show abstract

Computation-Directed Molecular Design, Synthesis, and Fungicidal Activity of Succinate Dehydrogenase Inhibitors

Cited by 2 publications

References 32 publications

Fungicidal Activity of New Pyrrolo[2,3-d]thiazoles and Their Potential Action on the Tryptophan Metabolic Pathway and Wax Biosynthesis

Fungicidal Activity of New Pyrrolo[2,3-d]thiazoles and Their Potential Action on the Tryptophan Metabolic Pathway and Wax Biosynthesis

Recent Advances in Design and Development of Diazole and Diazine Based Fungicides (2014–2023)

Contact Info

Product

Resources

About