Synthesis and antifungal activity of novel 1,2,4‐triazole derivatives containing an amide moiety

Wu, Weilong; Jiang, Yang-Ming; Fei, Qiang; Du, Hongguang; Yang, Mao‐Fa

doi:10.1002/jhet.3874

Cited by 26 publications

(8 citation statements)

References 25 publications

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“…Triazole derivatives have attracted considerable interest in the scientific community due to their vast range of biological activities. In addition to antifungal action [ 14 , 15 , 16 , 17 , 18 , 19 ], they were shown to possess other antimicrobial effects such as antibacterial, including anti-tuberculous activity [ 20 , 21 , 22 , 23 , 24 ], antiparasitic [ 25 , 26 , 27 ] and anti-HIV effects [ 28 ] as well as anticholinesterase [ 29 ], antiangiogenic [ 30 ], anticancer [ 31 , 32 ], antidiabetic [ 33 , 34 ] and anticonvulsant activities [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

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Herein we report the synthesis of some new 1H-1,2,4-triazole functionalized chromenols (3a–3n) via tandem reactions of 1-(alkyl/aryl)-2-(1H-1,2,4-triazole-1-yl) with salicylic aldehydes and the evaluation of their antifungal activity. In silico prediction of biological activity spectra with computer program PASS indicate that the compounds have a high novelty compared to the known antifungal agents. We did not find any close analog among the over 580,000 pharmaceutical agents in the Cortellis Drug Discovery Intelligence database at the similarity cutoff of 70%. The evaluation of antifungal activity in vitro revealed that the highest activity was exhibited by compound 3k, followed by 3n. Their MIC values for different fungi were 22.1–184.2 and 71.3–199.8 µM, respectively. Twelve from fourteen tested compounds were more active than the reference drugs ketoconazole and bifonazole. The most sensitive fungus appeared to be Trichoderma viride, while Aspergillus fumigatus was the most resistant one. It was found that the presence of the 2-(tert-butyl)-2H-chromen-2-ol substituent on the 4th position of the triazole ring is very beneficial for antifungal activity. Molecular docking studies on C. albicans sterol 14α-demethylase (CYP51) and DNA topoisomerase IV were used to predict the mechanism of antifungal activities. According to the docking results, the inhibition of CYP51 is a putative mechanism of antifungal activity of the novel chromenol derivatives. We also showed that most active compounds have a low cytotoxicity, which allows us to consider them promising antifungal agents for the subsequent testing activity in in vivo assays.

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Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

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“…Wu et al [ 136 ] evaluated the fungicidal activity of a novel series of 1,2,4-triazole derivatives containing an amide moiety. Compounds 71a, 71d, 71e, and 71f had the highest antifungal activity against Botrytis cinerea .…”

Section: 124 Triazole Scaffold For the Development Of Antifungal Agentsmentioning

confidence: 99%

Novel 1, 2, 4-Triazoles as Antifungal Agents

Kazeminejad

Marzi

Shiroudi

et al. 2022

BioMed Research International

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The development of innovative antifungal agents is essential. Some fungicidal agents are no longer effective due to resistance development, various side effects, and high toxicity. Therefore, the synthesis and development of some new antifungal agents are necessary. 1,2,4-Triazole is one of the most essential pharmacophore systems between five-membered heterocycles. The structure-activity relationship (SAR) of this nitrogen-containing heterocyclic compound showed potential antifungal activity. The 1,2,4-triazole core is present as the nucleus in a variety of antifungal drug categories. The most potent and broad activity of triazoles have confirmed them as pharmacologically significant moieties. The goal of this review is to highlight recent developments in the synthesis and SAR study of 1,2,4-triazole as a potential fungicidal compound. In this study, we provide the results of a biological activity evaluation using various structures and figures. Literature investigation showed that 1, 2, 4-triazole derivatives reveal the extensive span of antifungal activity. This review will assist researchers in the development of new potential antifungal drug candidates with high effectiveness and selectivity.

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“…High herbicidal activities have been reported for a series of novel triketones with N ‐substituted piperazine moiety 16 . Novel 1,2,4‐triazole derivatives with a piperazine moiety also show sufficient antifungal activities 17 . Furthermore, 1‐arylmethyl‐4‐[(trifluoromethyl)pyridin‐2‐yl] piperazine derivatives have demonstrated growth‐inhibiting or larvicidal functionality against the armyworm (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…16 Novel 1,2,4-triazole derivatives with a piperazine moiety also show sufficientantifungal activities. 17 Furthermore, 1-arylmethyl-4-[(trifluoromethyl)pyridin-2-yl] piperazine derivatives have demonstrated growth-inhibiting or larvicidal functionality against the armyworm (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and fungicidal activity of novel N‐substituted piperazine‐containing phenylpyridines against cucumber downy mildew

Wang

2022

Pest Management Science

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BACKGROUND Cucumber downy mildew (CDM) is a severe plant disease and affects the yield of cucumber production worldwide. As the resistance toward conventional fungicides is emerging as a ubiquitous issue, it is urgent to discover efficient fungicides with unique structures. RESULTS In this study, a series of novel phenylpyridine derivatives were designed and synthesized. Bioassays revealed that most of these compounds possessed excellent fungicidal activities against CDM. Among the phenylpyridine compounds, 2‐(4‐(4‐(tert‐butyl)benzyl)piperazin‐1‐yl)‐6‐phenylnicotinonitrile (C8) [half‐maximal effective concentration (EC50) = 4.40 mg L−1] displayed the highest activity, which was better than those of the commercial fungicides, such as azoxystrobin (EC50 = 42.77 mg L−1) and flumorph (EC50 = 41.94 mg L−1). Furthermore, the molecular electrostatic potential of high‐activity compound C8 indicated that nitrogen atom of the cyano group on the pyridine ring was in the negative region and may easily form hydrogen bonds and allow for electrostatic interactions with potential receptors. CONCLUSIONS This study demonstrated that the novel N‐substituted piperazine‐containing phenylpyridine derivatives could be further developed as a candidate compound to control CDM.

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Synthesis and antifungal activity of novel 1,2,4‐triazole derivatives containing an amide moiety

Cited by 26 publications

References 25 publications

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

Novel 1, 2, 4-Triazoles as Antifungal Agents

Design, synthesis, and fungicidal activity of novel N‐substituted piperazine‐containing phenylpyridines against cucumber downy mildew

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