Bioactive-guided structural optimization of 1,2,3-triazole phenylhydrazones as potential fungicides against Fusarium graminearum

Chen, Yiliang; Yao, Kai-Cheng; Wang, Kaiyan; Xiao, Cheng; Li, Ké; Khan, Bashir M.; Zhao, Shuangshuang; Yan, Wei; Ye, Yonghao

doi:10.1016/j.pestbp.2019.12.004

Cited by 15 publications

(8 citation statements)

References 20 publications

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“…graminearum as the positive control, the in vivo preventative effects of title compound C 17 against F. graminearum were fulfilled on the potted wheat cultivars, named Yangmai 2. − The distilled water (1.00 L) containing mung beans (30.00 g) was boiled for 15 min, filtered, and sterilized to obtain the liquid medium that could culture fungal spores. The newly activated cake of F.…”

Section: Materials and Methodsmentioning

confidence: 99%

Expedient Discovery for Novel Antifungal Leads Inhibiting Fusarium graminearum: 3-(Phenylamino)quinazolin-4(3H)-ones Deriving from Systematic Optimizations on a Tryptanthrin Structure

Wang¹,

Chai

Gu³

et al. 2022

J. Agric. Food Chem.

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The ever-increasing resistance of Fusarium graminearum has emerged as a pressing agricultural issue that could be settled by developing novel fungicides owning inimitable action mechanisms. With the aim of discovering novel antifungal leads inhibiting F. graminearum, a tryptanthrin structure was dexterously optimized to generate 30 novel quinazolin-4(3H)-one derivatives. The aforementioned optimization generated the molecule C 17 that owned exhilarating in vitro anti-F. graminearum effect (EC50 value = 0.76 μg/mL). Whereafter, the in vivo anti-F. graminearum preventative efficacy of the molecule C 17 was measured to be 59.5% at 200 μg/mL, which was approximately comparable with that of carbendazim (64.9%). Furthermore, morphological observations indicated that the molecule C 17 could cause the hypha to become slender and dense, distort the outline of cell walls, induce an increase in liposome numbers, and cause the reduction of mitochondria numbers. The above results have emerged as an obbligato complement for developing novel antifungal leads that could effectively control Fusarium head blight.

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Section: Materials and Methodsmentioning

confidence: 99%

Expedient Discovery for Novel Antifungal Leads Inhibiting Fusarium graminearum: 3-(Phenylamino)quinazolin-4(3H)-ones Deriving from Systematic Optimizations on a Tryptanthrin Structure

Wang¹,

Chai

Gu³

et al. 2022

J. Agric. Food Chem.

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“…Compound 143d showed the biggest and second most inhibitory activity against R. solani and S. sclerotiorum with EC50 values of 0.86 and 1.66 mg/mL, respectively. When comparing all compounds with similar halogen substituents, it has an unfavorable effect on antifungal activities, since the methylene group is found among the 1,2,3-triazoles and aromatic rings (Figure 74) [139]. Santos et al [140] tested nine synthetic 1,2,3-triazole derivatives against four Candida spp.…”

Section: 23-triazole Linked To Other Heterocyclicmentioning

confidence: 99%

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

Marzi

Farjam

Kazeminejad

et al. 2022

Journal of Chemistry

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A pharmacophore system has been found as 1,2,3-triazole, a five-membered heterocycle ring with nitrogen heteroatoms. These heterocyclic compounds can be produced using azide-alkyne cycloaddition processes catalyzed by ruthenium or copper. The bioactive compounds demonstrated antitubercular, antibacterial, anti-inflammatory, anticancer, antioxidant, antiviral, and antidiabetic properties. This heterocycle molecule, in particular, with one or more 1,2,3-triazole cores has been found to have the most powerful antifungal effects. The goal of this review is to highlight recent developments in the synthesis and structure-activity relationship (SAR) investigation of this prospective fungicidal chemical. Also there have been explained drugs and mechanism of action of a triazole compound with antifungal activity. This review will be useful in a variety of fields, including medicinal chemistry, organic chemistry, mycology, and pharmacology.

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“…If the wheat and its products contaminated by mycotoxins are eaten by humans and animals, they will cause vomiting, diarrhea, abortion, stillbirth, and other problems, which pose a great threat to the health of human beings and animals ( Puri and Zhong, 2010 ; Zheng et al., 2021 ). A comprehensive understanding of the molecular mechanism related to fungal growth, development, and pathogenicity is helpful to formulate effective measures to control this destructive pathogen and provide guidance for the development of new and efficient fungicides ( Becher et al., 2010 ; Chen et al., 2020 ).…”

Section: Introductionmentioning

confidence: 99%

FgMet3 and FgMet14 related to cysteine and methionine biosynthesis regulate vegetative growth, sexual reproduction, pathogenicity, and sensitivity to fungicides in Fusarium graminearum

et al. 2022

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Fusarium graminearum is a destructive filamentous fungus, which widely exists in wheat and other cereal crops. Cysteine and Methionine are unique sulfur-containing amino acids that play an essential role in protein synthesis and cell life, but their functions and regulation in F. graminearum remain largely unknown. Here we identified two proteins, FgMet3 and FgMet14 in F. graminearum, which are related to the synthesis of cysteine and methionine. We found FgMet3 and FgMet14 were localized to the cytoplasm and there was an interaction between them. FgMet3 or FgMet14 deletion mutants (ΔFgMet3 and ΔFgMet14) were deficient in vegetative growth, pigment formation, sexual development, penetrability and pathogenicity. With exogenous addition of cysteine and methionine, the vegetative growth and penetrability could be completely restored in ΔFgMet3 and ΔFgMet14, while sexual reproduction could be fully restored in ΔFgMet3 and partially restored in ΔFgMet14. ΔFgMet3 and ΔFgMet14 exhibited decreased sensitivity to Congo red stress and increased sensitivity to SDS, NaCl, KCl, Sorbitol, Menadione, and Zn ion stresses. Moreover, FgMet3 and FgMet14 nonspecifically regulate the sensitivity of F. graminearum to fungicides. In conclusion, FgMet3 and FgMet14 interacted to jointly regulate the development, pathogenicity, pigment formation, sensitivity to fungicides and stress factors in F. graminearum.

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Bioactive-guided structural optimization of 1,2,3-triazole phenylhydrazones as potential fungicides against Fusarium graminearum

Cited by 15 publications

References 20 publications

Expedient Discovery for Novel Antifungal Leads Inhibiting Fusarium graminearum: 3-(Phenylamino)quinazolin-4(3H)-ones Deriving from Systematic Optimizations on a Tryptanthrin Structure

Expedient Discovery for Novel Antifungal Leads Inhibiting Fusarium graminearum: 3-(Phenylamino)quinazolin-4(3H)-ones Deriving from Systematic Optimizations on a Tryptanthrin Structure

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

FgMet3 and FgMet14 related to cysteine and methionine biosynthesis regulate vegetative growth, sexual reproduction, pathogenicity, and sensitivity to fungicides in Fusarium graminearum

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