Synthesis and biological activity of novel 1,3,4-oxadiazole derivatives containing a pyrazole moiety

Yu, Wei; Zhai, Zhi-Wen; Wedge, David E.; Duke, Stephen O.; Wu, Hong‐Ke; Weng, Jian‐Quan; Tan, Cheng‐Xia; Zhang, Yonggang; Liu, Xinghai

doi:10.1007/s11164-019-04015-8

Cited by 12 publications

(12 citation statements)

References 53 publications

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“…Using acetonitrile as the solvent, the intermediates 5a−5v and 3-chloro-5-(trifluoromethyl) pyridin-2-ol were reacted for approximately 1.5 h under reflux to give the corresponding target compounds 6a− 6v. The structures of the target compounds were characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and 19 F NMR spectroscopy and high-resolution mass spectrometry (HRMS).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…As a highly efficient pharmacophore, 1,3,4-oxadiazole is not only used widely in drug design but also has extensive biological activities, 10,11 such as antibacterial, 12 herbicidal, 13 anti-inflammatory, 14 and insecticidal 15 properties. Furthermore, the molecules that contain 1,3,4-oxadiazole show excellent antibacterial activities against a number of plant bacterial pathogens, including R. solanacearum, 16 Xoo, 17 and Xac.…”

Section: ■ Introductionmentioning

confidence: 99%

“…All experiments were repeated three times. The inhibition rate was calculated using the following equation, where the corrected turbidity value of the negative control group was expressed as X and the turbidity value of the treatment group was expressed as Y. sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.1c04472.Characterization data, 1 H NMR,13 C NMR, and19 F NMR spectra, and HRMS data for the target compounds (PDF) State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China; orcid.org/0000-0002-9173-6608; Phone: +86-0851-88292090; Email: wujian2691@126.com, jwu6@ gzu.ede.cn; Fax: 86-851-88292090…”

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confidence: 99%

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Trifluoromethylpyridine 1,3,4-Oxadiazole Derivatives: Emerging Scaffolds as Bacterial Agents

Chen

Guo

et al. 2021

ACS Omega

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A new class of trifluoromethylpyridine 1,3,4-oxadiazole derivatives (6a–6v) was obtained, and their antibacterial activities were evaluated. Some of them exhibited good activity, particularly 6a, which had the highest in vitro activity against Ralstonia solanacearum (R. solanacearum) and Xanthomonas axonopodis pv. citri (Xac). The half-maximal effective concentrations (EC50) were 26.2 and 10.11 μg/mL, respectively, which were lower than those of commercial thiodiazole copper (97.2 and 35.3 μg/mL, respectively). Furthermore, 6q showed much higher activity against Xanthomonas oryzae pv. oryzae (Xoo) with an EC50 value of 7.2 μg/mL; this was superior to bismerthiazol (57.2 μg/mL). Collectively, our findings provide a foundation for the development of trifluoromethylpyridine 1,3,4-oxadiazole derivatives.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Trifluoromethylpyridine 1,3,4-Oxadiazole Derivatives: Emerging Scaffolds as Bacterial Agents

Chen

Guo

et al. 2021

ACS Omega

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“…For instance, the recent succinate dehydrogenase inhibitor (SDHI) fungicides pydiflumetofen, isoflucypram, and pyrapropoyne have pyrazole amide groups. Numerous biological activities can be performed by modifying the pyrazole scaffold, such as nematocidal [8][9][10], herbicidal [11,12], antimicrobial [13], antioxidant [14], fungicidal [15][16][17], anticancer [18], and insecticidal activities [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoromethylpyrazoyl moiety

et al. 2022

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In order to find new lead compounds with high pesticidal activity, a series of 1,3,4-oxadiazole thioether compounds ( 5 series) were designed by using penthiopyrad as a synthon. They were synthesized easily via five steps by using ethyl 4,4,4-trifluoro-3-oxobutanoate and triethyl orthoformate as starting materials. The synthesized compounds were characterized by 1 H NMR, 13 C NMR and HRMS. The compound 2-(benzylthio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole ( 5a ) was further determined by X-ray single-crystal diffraction. It crystallized in the monoclinic system, space group P2 1 /c , Z = 4. All the 1,3,4-oxadiazole thioether derivatives were screened for fungicidal activity against ten fungi and herbicidal activity against two weeds. The bioassay results indicated that some of the synthesized 1,3,4-oxadiazole compounds exhibited good fungicidal activity (> 50% inhibition) against the plant pathogens Sclerotinia sclerotiorum and Rhizoctonia solani at 50 μg/mL. Some of them exhibited certain herbicidal activity, and compounds 2-((3-chlorobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole ( 5e) and 2-((4-bromobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole (5 g) had bleach effect. Molecular docking is to find the best fit orientation of the 2-((4-bromobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole (5 g) molecule with the SDH protein (PDB: 2FBW). The docking results indicate that the compound 5 g and the lead compound penthiopyrad have similar binding interactions with SDH and carbonyl is a key group for these compounds. Supplementary Information The online version contains supplementary material available at 10.1007/s11164-022-04839-x.

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“…The structures of 2aminopyridines and its derivatives are a class of nitrogen heterocyclic compounds that have drawn much attention, due to their biological and pharmaceutical activities [19][20][21][22][23][24]. The development of clean synthetic routes towards nitrogen-containing heterocycles is of great importance to both synthetic and medicinal chemists [25][26][27]. So, it is important to find simple and convenient procedures for the synthesis of 2-aminopyridines with different substitutes in their moiety, with the aim of obtaining some novel heterocyclic compounds with potentially enhanced properties.…”

Section: Introductionmentioning

confidence: 99%

Efficient multicomponent synthesis of 2-aminopyridines catalysed by basic mesoporous materials

et al. 2020

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An efficient and green procedure for the synthesis of 2aminopyridines derivatives via four-component reaction of acetophenone, malononitrile, triethoxymethane and different primary amines has been developed using different surfactant-containing mesoporous catalysts. The advantages of this approach are easy operational method, high product yields and reusable catalysts without losing their catalytic activity.

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Synthesis and biological activity of novel 1,3,4-oxadiazole derivatives containing a pyrazole moiety

Cited by 12 publications

References 53 publications

Trifluoromethylpyridine 1,3,4-Oxadiazole Derivatives: Emerging Scaffolds as Bacterial Agents

Trifluoromethylpyridine 1,3,4-Oxadiazole Derivatives: Emerging Scaffolds as Bacterial Agents

Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoromethylpyrazoyl moiety

Efficient multicomponent synthesis of 2-aminopyridines catalysed by basic mesoporous materials

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