Antiviral Activities of Novel Myricetin Derivatives Containing 1,3,4‐Oxadiazole Bisthioether

Peng, Feng; Liu, Tingting; Cao, Xiaohong; Wang, Qifan; Liu, Fang; Liu, Liwei; He, Ming; Xue, Wei

doi:10.1002/cbdv.202100939

Cited by 13 publications

(6 citation statements)

References 47 publications

(43 reference statements)

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“…The synthetic route of title compounds D1 – D19 is illustrated in Scheme 1 , based on the synthesis method outlined in reference [ 41 , 42 , 43 , 44 , 45 , 46 ]. The intermediate a was synthesized using substituted phenylhydrazine, ethyl acetoacetate or ethyl benzoylacetate, DMF ( N , N -Dimethylformamide) and POCl 3 (phosphorus oxychloride).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of Myricetin Derivatives Containing Pyrazole Piperazine Amide

Liu

Cao

Zhang

et al. 2023

IJMS

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In this paper, a series of derivatives were synthesized by introducing the pharmacophore pyrazole ring and piperazine ring into the structure of the natural product myricetin through an amide bond. The structures were determined using carbon spectrum and hydrogen spectrum high-resolution mass spectrometry. Biological activities of those compounds against bacteria, including Xac (Xanthomonas axonopodis pv. Citri), Psa (Pseudomonas syringae pv. Actinidiae) and Xoo (Xanthomonas oryzae pv. Oryzae) were tested. Notably, D6 exhibited significant bioactivity against Xoo with an EC50 value of 18.8 μg/mL, which was higher than the control drugs thiadiazole-copper (EC50 = 52.9 μg/mL) and bismerthiazol (EC50 = 69.1 μg/mL). Furthermore, the target compounds were assessed for their antifungal activity against ten plant pathogenic fungi. Among them, D1 displayed excellent inhibitory activity against Phomopsis sp. with an EC50 value of 16.9 μg/mL, outperforming the control agents azoxystrobin (EC50 = 50.7 μg/mL) and fluopyram (EC50 = 71.8 μg/mL). In vitro tests demonstrated that D1 possessed curative (60.6%) and protective (74.9%) effects on postharvest kiwifruit. To investigate the active mechanism of D1, its impact on SDH activity was evaluated based on its structural features and further confirmed through molecular docking. Subsequently, the malondialdehyde content of D1-treated fungi was measured, revealing that D1 could increase malondialdehyde levels, thereby causing damage to the cell membrane. Additionally, the EC50 value of D16 on P. capsici was 11.3 μg/mL, which was superior to the control drug azoxystrobin (EC50 = 35.1 μg/mL), and the scanning electron microscopy results indicated that the surface of drug-treated mycelium was ruffled, and growth was significantly affected.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of Myricetin Derivatives Containing Pyrazole Piperazine Amide

Liu

Cao

Zhang

et al. 2023

IJMS

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“…For example, compounds 1 ( K d = 0.003 μM) and 2 ( K d = 0.256 μM) (myricetin derivative containing oxadiazole linked with flexible bridges) exhibited significantly improved curative and protective activities against TMV compared to ningnanmycin ( K d = 2.726 μM) . However, compared to compound 1 , compound 3 ( K d = 0.029 μM), exhibited reduced activity against TMV despite containing the same scaffold . This observation suggests that the length of the flexible bridge is a critical parameter governing the antiviral activity of these compounds.…”

Section: Benzopyran Active Compounds For Agricultural Applicationmentioning

confidence: 99%

“…49 However, compared to compound 1, compound 3 (K d = 0.029 μM), exhibited reduced activity against TMV despite containing the same scaffold. 50 This observation suggests that the length of the flexible bridge is a critical parameter governing the antiviral activity of these compounds. In addition, the introduction of electron-donating groups on the benzene ring connected with oxadiazole also improves the antiviral activity of the scaffold compound; therefore, oxadiazole was replaced with thiadiazole or its mode of linking with the pyranoid ring was altered to obtain compounds 4 and 5, respectively.…”

Section: ■ Introductionmentioning

confidence: 99%

Recent Advances and Outlook of Benzopyran Derivatives in the Discovery of Agricultural Chemicals

Liu,

Zhang,

Zou

et al. 2024

J. Agric. Food Chem.

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Scaffold structures, new mechanisms of action, and targets present enormous challenges in the discovery of novel pesticides. The discovery of new scaffolds is the basis for the continuous development of modern agrochemicals. Identification of a good scaffold such as triazole, carbamate, methoxy acrylate, pyrazolamide, pyrido-pyrimidinone mesoionic, and bisamide often leads to the development of a new series of pesticides. In addition, pesticides with the same target, including the inhibitors of succinate dehydrogenase (SDH), oxysterol-binding-protein, and p-hydroxyphenyl pyruvate dioxygenase (HPPD), may have the same or similar scaffold structure. Recent years have witnessed significant progress in the discovery of new pesticides using natural products as scaffolds or bridges. In recent years, there have been increasing reports on the application of natural benzopyran compounds in the discovery of new pesticides, especially osthole and coumarin. A systematic and comprehensive review of benzopyran active compounds in the discovery of new agricultural chemicals is helpful to promote the discussion and development of benzopyran active compounds. Therefore, this work systematically reviewed the research and application of benzopyran derivatives in the discovery of agricultural chemicals, summarized the antiviral, herbicidal, antibacterial, fungicidal, insecticidal, nematicidal and acaricidal activities of benzopyran active compounds, and discussed the structural−activity relationship and mechanism of action. In addition, some active fragments were recommended to further optimize the chemical structure of benzopyran active compounds based on reference information.

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“…Myricetin is a class of natural flavonoids. Pharmacological research shows that myricetin possesses antiviral, 13,14 antibacterial, [15][16][17] anticancer, [18][19][20][21] antioxidant 22 and other biological activities. Because of the advantages of various plant sources and biological activity, the myricetin flavonoids have attracted widespread attention and research.…”

Section: Introductionmentioning

confidence: 99%

Novel 1,3,4‐oxadiazole sulfonate/carboxylate flavonoid derivatives: synthesis and biological activity

Peng

Liu

Zhu

et al. 2022

Pest Management Science

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Background: With the long-term use of traditional bactericides and antiviral agents, drug resistance has become increasingly prominent, resulting in impaired crop growth and yields. Based on this, the introduction of small molecular active groups into natural products has become the direction of research for green pesticides.Results: In this study, novel 1,3,4-oxadiazole sulfonate/carboxylate flavonoid derivatives were explored. Among them, D4 exhibited good inhibitory effects on plant bacteria. It is worth mentioning that D4 (15 ∼g ml −1 ) exhibited an excellent median effective concentration (EC 50 ) value against Xanthomonas oryzae pv. oryzae (Xoo), which was better than bismerthiazol (73 ∼g ml −1 ) and thiodiazole copper (100 ∼g ml −1 ). The EC 50 for D4 was much lower than the two positive controls (bismerthiazol, thiodiazole copper), making D4 more potent in this assay of bacterial growth inhibition. In addition, mechanism research using scanning electron microscopy revealed that D4 could cause deformation or rupture of the cell membranes of Xoo and Pseudomonas syringae pv. actinidiae. Moreover, D4 exhibited the best EC 50 for in vivo curative (132 ∼g ml −1 ) and protective (101 ∼g ml −1 ) activities against tobacco mosaic virus, which were more effective than ningnanmycin. Microscale thermophoresis data suggested that D4 [dissociation constant (K d ) = 0.038 ± 0.011 ∼mol L −1 ] exhibited a stronger binding capacity than the control agent ningnanmycin (K d = 4.707 ± 2.176 ∼mol L −1 ). Conclusion:The biological activity data and mode of action demonstrated that D4 had the best antibacterial and antiviral effects. Compound D4 discovered in the current work may be a very promising agricultural drug.

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Antiviral Activities of Novel Myricetin Derivatives Containing 1,3,4‐Oxadiazole Bisthioether

Cited by 13 publications

References 47 publications

Synthesis and Biological Activity of Myricetin Derivatives Containing Pyrazole Piperazine Amide

Synthesis and Biological Activity of Myricetin Derivatives Containing Pyrazole Piperazine Amide

Recent Advances and Outlook of Benzopyran Derivatives in the Discovery of Agricultural Chemicals

Novel 1,3,4‐oxadiazole sulfonate/carboxylate flavonoid derivatives: synthesis and biological activity

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