Design, Synthesis, and Antifungal Activity of Novel Benzimidazole Derivatives Bearing Thioether and Carbamate Moieties

Lei, Yang

doi:10.1155/2022/8646557

Cited by 2 publications

(2 citation statements)

References 18 publications

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“…For a long time, benzimidazole derivatives as strong and safe antifungal medicines have drawn increasing interest among the pharmaceuticals used to treat fungal infections. Carbendazole, benomyl, and thiabendazole have been frequently used among them. − Triazoles, a type of heterocyclic molecule, are favored scaffolds in a variety of fields. Fluconazole, itraconazole, and voriconazole are antifungal medicines available for therapeutic use that contain 1,2,4-triazole fragments. − In recent years, many studies have been conducted on the antifungal activities of triazoles. − Antifungal drugs with benzimidazole and triazole structures and the chemical structure of the designed compounds are shown in Figure .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Benzimidazole-1,2,4-triazole Derivatives as Potential Antifungal Agents Targeting 14α-Demethylase

et al. 2023

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Invasive fungal infections (IFIs) are increasing as major infectious diseases around the world, and the limited efficacy of existing medications has resulted in substantial morbidity and death in patients due to the lack of effective antifungal agents and serious drug resistance. In this study, a series of benzimidazole-1,2,4-triazole derivatives (6a−6l) were synthesized and characterized by 1 H NMR, 13 C NMR, and HR-MS spectral analysis. All the target compounds were screened for their in vitro antifungal activity against four fungal strains, namely, C. albicans, C. glabrata, C. krusei, and C. parapsilopsis. The synthesized compounds exhibited significant antifungal potential, especially against C. glabrata. Three compounds (6b, 6i, and 6j) showed higher antifungal activity with their MIC values (0.97 μg/mL) compared with voriconazole and fluconazole. Molecular docking provided a possible binding mode of compounds 6b, 6i, and 6j in the 14α-demethylase active site. Our studies suggested that the benzimidazole-1,2,4-triazole derivatives can be used as a new fungicidal lead targeting 14α-demethylase for further structural optimization. In addition, their effects on the L929 cell line were also investigated to evaluate the cytotoxic effects of the compounds. SEM analyses were performed to examine the effects of compounds 6a, 6i, and 6j on C. glabrata cells under in vivo experimental conditions.

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Section: Introductionmentioning

confidence: 99%

“…Carbendazole, benomyl, and thiabendazole have been frequently used among them. 18 − 20 Triazoles, a type of heterocyclic molecule, are favored scaffolds in a variety of fields. Fluconazole, itraconazole, and voriconazole are antifungal medicines available for therapeutic use that contain 1,2,4-triazole fragments.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzimidazole-1,2,4-triazole Derivatives as Potential Antifungal Agents Targeting 14α-Demethylase

et al. 2023

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Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

Xiao,

Song,

Xiong

et al. 2023

Molecules

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At present, phenolic acid derivatives and triazole derivatives have a good antifungal effect, which has attracted widespread attention. A series of novel phenolic acid triazole derivatives were synthesized, and their structures were characterized by IR, MS, NMR, and X-ray crystal diffraction. Compound methyl 4-(2-bromoethoxy)benzoate, methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate, 4-(2-(1H-1,2,4-triazol-1-yl)ethoxy)benzoic acid and 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)-3-methoxybenzoic acid crystallize in the monoclinic system with space group P21/n, the monoclinic system with space group P21, the monoclinic system with space group P21 and the orthorhombic system with space group Pca21, respectively. At a concentration of 100 μg/mL and 200 μg/mL, the antifungal activity against seven plant pathogen fungi was determined. Compound methyl 4-(2-bromoethoxy)benzoate has the best inhibitory effect on Rhizoctonia solani AG1, and the inhibitory rate reached 88.6% at 200 μg/mL. The inhibitory rates of compound methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate against Fusarium moniliforme and Sphaeropsis sapinea at a concentration of 200 μg/mL were 76.1% and 75.4%, respectively, which were better than that of carbendazim.

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Design, Synthesis, and Antifungal Activity of Novel Benzimidazole Derivatives Bearing Thioether and Carbamate Moieties

Cited by 2 publications

References 18 publications

Synthesis of Benzimidazole-1,2,4-triazole Derivatives as Potential Antifungal Agents Targeting 14α-Demethylase

Synthesis of Benzimidazole-1,2,4-triazole Derivatives as Potential Antifungal Agents Targeting 14α-Demethylase

Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

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