Design, synthesis and biological evaluation of pyrazole-aromatic containing carboxamides as potent SDH inhibitors

Yu, Bin; Zhao, Bin; Hao, Zesheng; Chen, Lei; Cao, Lixin; Guo, Xiaofeng; Zhang, Nailou; Yang, Dongyan; Tang, Liang‐Fu; Fan, Zhijin

doi:10.1016/j.ejmech.2021.113230

Cited by 38 publications

(39 citation statements)

References 34 publications

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“…In order to evaluate the binding modes between target compounds (5e and 5k) with target enzymes succinate dehydrogenase (SDH; Yan et al, 2019 ; Yu et al, 2021 ), the molecular docking was conducted using Surflex-Dock program in the Sybyl-X software (version 2.1.1), and interaction analyzed using Ligplot + client (version 2.2.4) and Pymol client. The crystal structure of SDH was downloaded from the Protein Data Bank (PDB code: 2FBW).…”

Section: Methodsmentioning

confidence: 99%

Development of 1,3,4-Oxadiazole Derived Antifungal Agents and Their Application in Maize Diseases Control

Zhang

et al. 2022

Front. Plant Sci.

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Maize is an important food crop and its fungal disease has become a limiting factor to improve the yield and quality of maize. In the control of plant pathogens, commercial fungicides have no obvious effect on corn diseases due to the emergence of drug resistance. Therefore, it is of great significance to develop new fungicides with novel structure, high efficiency, and low toxicity to control maize diseases. In this paper, a series of 1,3,4-oxadiazole derivatives were designed and synthesized from benzoyl hydrazine and aromatic aldehydes through condensation and oxidation cyclization reaction. The antifungal activity of oxadiazole derivatives against three maize disease pathogens, such as Rhizoctonia solani (R. solani), Gibberella zeae (G. zeae), and Exserohilum turcicum (E. turcicum), were evaluated by mycelium growth rate method in vitro. The results indicated that most of the synthesized derivatives exhibited positive antifungal activities. Especially against E. turcicum, several compounds demonstrated significant antifungal activities and their EC50 values were lower than positive control carbendazim. The EC50 values of compounds 4k, 5e, and 5k were 50.48, 47.56, 32.25 μg/ml, respectively, and the carbendazim was 102.83 μg/ml. The effects of active compounds on E. turcicum microstructure were observed by scanning electron microscopy (SEM). The results showed that compounds 4k, 5e, and 5k could induce the hyphae of E. turcicum to shrink and collapse obviously. In order to elucidate the preliminary mechanism of oxadiazole derivatives, the target compounds 5e and 5k were docked with the theoretical active site of succinate dehydrogenase (SDH). Compounds 5e and 5k could bind to amino acid residues through hydrophobic contact and hydrogen bonds, which explained the possible mechanism of binding between the inhibitor and target protein. In addition, the compounds with antifungal activities had almost no cytotoxicity to MCF-7. This study showed that 1,3,4-oxadiazole derivatives were worthy for further attention as potential antifungal agents for the control of maize diseases.

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Section: Methodsmentioning

confidence: 99%

Development of 1,3,4-Oxadiazole Derived Antifungal Agents and Their Application in Maize Diseases Control

Zhang

et al. 2022

Front. Plant Sci.

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“…In vitro antifungal activities of compounds 7a-7u against Alternaria solani, B. cinerea, Cercospora arachidicola, Gibberella zeae, Phytophthora infestans (Mont) de Bary, Physalospora piricola, Pellicularia sasakii, Rhizoctonia cerealis, S. sclerotiorum were conducted at 50 μg/mL by using the mycelium growth-inhibition method according to a reported method [27]. Any compounds with inhibition over 70% were further evaluated for their median effective concentrations (EC 50 ) according to the reported procedures [27,28].…”

Section: Antifungal Activity Testmentioning

confidence: 99%

Design, synthesis and fungicidal activity of 3,4-dichloroisothiazolocoumarin-containing strobilurins

Wei

et al. 2021

Mol Divers

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Twenty-one novel 3,4-dichloroisothiazolocoumarin-containing strobilurins were rationally designed and synthesized. Preliminary bioassay showed that compounds 7c, 7h and 7l exhibited over 80% inhibitory rate against Sclerotinia sclerotiorum at 50 μg/mL, 7c exhibited good activity against S. sclerotiorum with median effective concentration (EC 50 ) of 4.08 μg/mL, while the positive control coumoxystrobin showed EC 50 of 1.00 μg/mL. In addition, 7d showed better fungicidal activity with a lower EC 50 value of 7.65 μg/mL against Botrytis cinerea than that of positive control trifloxystrobin with its EC 50 value of 21.96 μg/mL. This study indicated that 3,4-dichloroisothiazolocoumarin-containing strobilurin was a promising fungicide lead deserved for further study.

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“…The detail docking procedure was conducted according to the reported literature. 26 The figure was exported from SYBYL and drawn by Pymol.…”

Section: Molecular Dockingmentioning

confidence: 99%

“…1,2,3‐Thiadiazole and isothiazole derivatives possess a broad spectrum of biological activity such as fungicidal, antiviral and SAR activity (also called induction activity) discovered in our previous studies 26,27 . Literature analyses revealed that all commercialized carboxamide‐containing plant elicitors contain an amine moiety with only one simple aromatic group.…”

Section: Introductionmentioning

confidence: 98%

“…24,25 1,2,3-Thiadiazole and isothiazole derivatives possess a broad spectrum of biological activity such as fungicidal, antiviral and SAR activity (also called induction activity) discovered in our previous studies. 26,27 Literature analyses revealed that all commercialized carboxamide-containing plant elicitors contain an amine moiety with only one simple aromatic group. It is supposed that an introduction of a substitution with two phenyl/heterocycle rings in many pesticide molecules would improve physicochemical properties and pesticide activity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

Yang

Калинина

et al. 2021

Pest Management Science

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BACKGROUND: Plant elicitors are a class of plant protection agents that can stimulate plant immunity against phytopathogen without a potential resistance problem. In searching for novel plant elicitor candidates, a series of novel N-(2-phenyl-3-pyridyl) thiadiazole/isothiazole carboxamide analogs were designed and synthesized. RESULTS:In vitro bioassay showed that all new compounds exhibited weak direct fungicidal activity. However, compounds 3b, 3g, 3n and 3o showed broad spectrum of in vivo activity against four plant fungi tested. In particularly, 3g showed 80% activity against Rhizoctonia solani in a glasshouse at a concentration of 1 ∼g mL -1 . For induction activity of tobacco against tobacco mosaic virus (TMV), compounds 3c and 3v showed 67% and 68% inhibitory activity, respectively, which were superior to the positive controls ribavirin and ningnanmycin. Compound 3g showed moderate induction activity (41%). Reverse transcription quantitative polymerase chain reaction (RT-qPCR) analysis found that, 3g could up-regulate expression of genes that are related to reactive oxygen species (ROS), pathogenesis-related protein (PRP) and salicylic acid (SA) signalling.CONCLUSION: These results indicated that 3g as an elicitor candidate might act on the SA signalling pathway. According to our findings, N-(2-phenyl-3-pyridyl) thiadiazole/isothiazole carboxamide analogs might be promising lead scaffolds as a novel plant elicitor for further investigation.

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Design, synthesis and biological evaluation of pyrazole-aromatic containing carboxamides as potent SDH inhibitors

Cited by 38 publications

References 34 publications

Development of 1,3,4-Oxadiazole Derived Antifungal Agents and Their Application in Maize Diseases Control

Development of 1,3,4-Oxadiazole Derived Antifungal Agents and Their Application in Maize Diseases Control

Design, synthesis and fungicidal activity of 3,4-dichloroisothiazolocoumarin-containing strobilurins

Synthesis of novel N‐(2‐phenyl‐3‐pyridyl) thiadiazole/isothiazole carboxamide analogs as potent plant elicitors

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