Design, Synthesis, and Acaricidal Activities of Novel Pyrazole Acrylonitrile Compounds

Huang, Danling; Huang, Mingzhi; Liu, Aiping; Liu, Xing‐Ping; Liu, Weidong; Chen, Xiaoyang; Xue, Hansong; Sun, Jiong; Yin, Dulin; Wang, Xiaoguang

doi:10.1002/jhet.2682

Cited by 18 publications

(9 citation statements)

References 15 publications

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“…Our target compounds A1−A27 were accessible by nucleophilic substitution and esterification reactions according to the reported method as shown in Scheme 3. 13,14,35 As shown in Table 3, the clogP value, which was the fundamental physicochemical property of target compounds related to acaricidal activities, was calculated by the Canvas program (Schrodinger, LLC, 2015). 39 The clogP values of our novel silicon-containing pyrazolyl acrylonitrile derivatives ranged from 5.24 to 6.96, which was close to that of the positive control cyenopyrafen (clogP = 5.45), demonstrating the acaricides likeness and potential acaricidal activities of the title compounds.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon–Silicon Bioisosteric Replacement Strategy

Zhou,

Li,

Qian

et al. 2023

J. Agric. Food Chem.

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The identification of novel pyrazolyl acrylonitrile acaricides with improved properties is of great value for the control of phytophagous mites. A series of innovative silicon-containing pyrazolyl acrylonitriles were rationally designed by applying a bioisosteric carbon−silicon replacement strategy and prepared based on novel synthetic methodology. As a result of our research, we discovered compound A25 which possesses outstanding acaricidal activity. With an LC 50 value of 0.062 mg/L, compound A25 was found to be 2.3-fold and 1.9-fold more potent than the commercial acaricides cyenopyrafen and cyetpyrafen, respectively. Enzymatic inhibitory assay indicated that the active principle M1 of compound A25 possesses an IC 50 value of 2.32 μM against Tetranychus cinnabarinus SDH, which was about twofold superior compared to the active metabolites of cyenopyrafen (IC 50 = 4.72 μM). Molecular docking study showed that the active metabolites 2 and 3 and their corresponding silicon counterparts form H-bonds and cation−π interaction with the residues of Trp165, Tyr433, and Arg279.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon–Silicon Bioisosteric Replacement Strategy

Zhou,

Li,

Qian

et al. 2023

J. Agric. Food Chem.

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“…In recent years, the scope of SDH inhibitors (SDHI) that act by blocking succinate dehydrogenase, the complex II of the mitochondrial electron transport chain, was gradually extended to agricultural mite control. As the first SDHI acaricide, Otsuka introduced cyflumetofen to the market in 2007. , Since then, other complex II acaricide products were identified, developed, and brought to the market, mainly cyenopyrafen (by Nissan in 2009), − pyflubumide (by Nihon Nohyaku in 2015), − and cyetpyrafen (by Sinochem in 2017) . These novel acaricides targeting SDH bear novel chemical structures, exhibit a new mode of action for mite control, and have no cross resistance to the existing acaricide products.…”

Section: Design Of Silicon-containing Complex II Acaricidesmentioning

confidence: 99%

Silicon-Containing Complex II Acaricides─Design, Synthesis, and Pharmacological Optimization

Zhou

Wang

Quan

et al. 2022

J. Agric. Food Chem.

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Bioisosteric replacement has been proven to be a powerful strategy in life science research. In this review, general aspects of carbon–silicon bioisosteric substitution and its applications in pharmaceutical and crop protection research are described. Carbon and their silicon analogues possess similar intrinsic properties. Replacing carbon with silicon in pharmaceuticals and pesticides has shown to result in positive effects on efficacy and selectivity, physicochemical properties, and bioavailability and also to eliminate or improve human or environmental safety properties as well as to provide novelty and new intellectual property in many cases. Furthermore, the application of carbon–silicon substitution in the search for new complex II acaricides is highlighted. This research led to the discovery of sila-cyflumetofen 23a and other silicon-containing analogues of cyflumetofen that match or exceed the acaricidal activity of cyflumetofen. The molecular design strategy, synthetic aspects, biological activity, computational modeling work, and structure–activity relationships will be discussed.

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“…[ 155 ] In another study on similar compounds, Huang et al reported that 85 , 86 , 87 , 88 , and 89 (Table 3) showed significant acaricidal activities against Tetranchus urticae , with LC 50 values of 0.364, 0.313, 0.324, and 0.307 mg/l, respectively. [ 156 ]…”

Section: Biological Activities Of Acrylonitrilesmentioning

confidence: 99%

Insights into the chemistry and therapeutic potential of acrylonitrile derivatives

Tan

Zengin

2021

Archiv der Pharmazie

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Acrylonitrile is a fascinating scaffold widely found in many natural products, drugs, and drug candidates with various biological activities. Several drug molecules such as entacapone, rilpivirine, teriflunomide, and so forth, bearing an acrylonitrile moiety have been marketed. In this review, diverse synthetic strategies for constructing desired acrylonitriles are discussed, and the different biological activities and medicinal significance of various acrylonitrile derivatives are critically evaluated. The information gathered is expected to provide rational guidance for the development of clinically useful agents from acrylonitriles.

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Design, Synthesis, and Acaricidal Activities of Novel Pyrazole Acrylonitrile Compounds

Cited by 18 publications

References 15 publications

Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon–Silicon Bioisosteric Replacement Strategy

Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon–Silicon Bioisosteric Replacement Strategy

Silicon-Containing Complex II Acaricides─Design, Synthesis, and Pharmacological Optimization

Insights into the chemistry and therapeutic potential of acrylonitrile derivatives

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