Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring

Yan, Zhongzhong; Liu, Aiping; Huang, Mingzhi; Liu, Minhua; Hui, Pei; Huang, Lu; Yi, Hai-Bo; Liu, Weidong; Hu, Aiguo

doi:10.1016/j.ejmech.2018.02.036

Cited by 67 publications

(28 citation statements)

References 32 publications

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“…frac.info), succinate dehydrogenase inhibitor (SDHI) class is the fastest growing in terms of new compounds produced and launched into the market. 2,3 To date, 23 commercial SDHI fungicides have been approved for plant protection since the first launch of carboxin in 1966, and extensively applied to combat destructive plant fungi, such as Sclerotinia sclerotiorum, Rhizoctonia solani, and Botrytis cinerea. [4][5][6] In most of SDHI fungicides, the amide bonds are directly linked to the aromatic ring and polar moiety ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Studies on the novel pyridine sulfide containing SDH based heterocyclic amide fungicide

Hua

Liu

et al. 2020

Pest Management Science

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BACKGROUND: Succinate dehydrogenase (SDH) has been identified as one of the most significant targets for fungicide discovery. To date, 23 commercial SDH inhibitor (SDHI) fungicides have been approved for plant protection since the first launch of carboxin in 1966, and extensively applied to combat destructive plant fungi. RESULTS:In this project, 20 novel pyridine sulfide derivatives containing SDH-based heterocyclic amide fungicide were designed, synthesized, and characterized by proton nuclear magnetic resonance ( 1 H-NMR), carbon-13 ( 13 C)-NMR and highresolution mass spectrometry (HRMS). In vitro fungicidal activity experiment, the target compound I-1 displayed excellent inhibitory rates against the common agricultural pathogens with half maximal effective concentration (EC 50 ) values of 5.2 to 39.8 ∼g mL −1 . The in vivo fungicidal activities demonstrated that the compound I-1 could effectively prevent Botrytis cinerea from infecting tomato and cucumber leaves with the preventative rates of 67% and 50%. The mitochondrial membrane potential detection, SDH enzyme assay and the molecular docking simulation revealed that the mechanism of action of the compound I-1 and the relevant interactions with the target enzyme may be similar to those of the control fluopyram.CONCLUSION: The biological activity screening and validation of mechanism of action indicated that the compound I-1 could be identified as a potential SDH inhibitor for further study.

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Section: Introductionmentioning

confidence: 99%

Studies on the novel pyridine sulfide containing SDH based heterocyclic amide fungicide

Hua

Liu

et al. 2020

Pest Management Science

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“…The growing incidence of microorganisms that resist antimicrobials is a constant concern for the scientific community. Pyrazoles have always been considered as a scaffold-of-choice in designing novel therapeutic agents because of their anti-inflammatory, anti-tumor, antihyperglycemic, antipyretic, analgesic, antibacterial, and antifungal properties [9][10][11][12][13][14][15][16]. In this work, we present a synthesis, structural characterization, and investigation of the biological, spectroscopic, and thermal properties of two new pyrazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity against A549 Human Lung Cancer Cells and ADMET Analysis of New Pyrazole Derivatives

Czylkowska

Szczesio

Raducka

et al. 2021

IJMS

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Two new pyrazole derivatives, namely compound 1 and compound 2, have been synthesized, and their biological activity has been evaluated. Monocrystals of the obtained compounds were thoroughly investigated using single-crystal X-ray diffraction analysis, FTIR spectroscopy, and NMR spectroscopy. The results gathered from all three techniques are in good agreement, provide complete information about the structures of 1 and 2, and confirm their high purity. Thermal properties were studied using thermogravimetric analysis; both 1 and 2 are stable at room temperature. In order to better characterize 1 and 2, some physicochemical and biological properties have been evaluated using ADMET analysis. The cytotoxic activity of both compounds was determined using the MTT assay on the A549 cell line in comparison with etoposide. It was determined that compound 2 was effective in the inhibition of human lung adenocarcinoma cell growth and may be a promising compound for the treatment of lung cancer.

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“…Stock solution of every test compound was prepared in DMF at a concentration of 1000 mg /L and then the solution was diluted to the required test concentration (50-500 mg/L) with water containing Tween 80 (0.40 mg/L) [14][15][16][17].…”

Section: Biological Assaymentioning

confidence: 99%

Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives

Liu

et al. 2019

Heterocyclic Communications

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A series of novel imidazo[4,5-b]pyridine derivatives were synthesized and their structures were characterized by NMR spectroscopy, mass spectrometry and elemental analysis. The results of bioassays showed that some compounds exhibit good fungicidal activity against Puccinia polysora In particular, compound 7b showed an EC50 value of 4.00 mg/L, which was comparable with that of tebuconazole. Besides, preliminary structure-activity relationship was discussed.

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Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring

Cited by 67 publications

References 32 publications

Studies on the novel pyridine sulfide containing SDH based heterocyclic amide fungicide

Studies on the novel pyridine sulfide containing SDH based heterocyclic amide fungicide

Cytotoxic Activity against A549 Human Lung Cancer Cells and ADMET Analysis of New Pyrazole Derivatives

Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives

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