Synthesis, insecticidal evaluation and 3D‐QSAR study of novel anthranilic diamide derivatives as potential ryanodine receptor modulators

Liu, Jingbo; Li, Fengyun; Li, Yuxin; Zhang, Xiulan; Hua, Xuewen; Xiong, Lixia; Li, Zhengming

doi:10.1002/ps.5213

Cited by 18 publications

(22 citation statements)

References 25 publications

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“…The calcium imaging experiment of Ij, In, Ip, and chlorantraniliprole was conducted according to the procedures described in our previous research. 38 Calibration of the fluorescence signal was achieved by using the method of Takahashi et al with minor modifications. 39 Each experiment was repeated at least six times.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Synthesis, Insecticidal Evaluation, and 3D-QASR of Novel Anthranilic Diamide Derivatives Containing N-Arylpyrrole as Potential Ryanodine Receptor Activators

Wang

et al. 2020

J. Agric. Food Chem.

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To cope with the global food shortage and insect pest, there is an urgent need to discover new pesticides with novel modes of actions. Ryanodine receptor (RyR) insecticides showed great promise in integrated pest management. Herein, we report the synthesis of novel anthranilic diamide derivatives incorporating pyrrole moieties targeting at insect RyRs. The structures were confirmed by 1H NMR, 13C NMR, 19F NMR, and high-resolution mass spectrometry. The preliminary bioassay results indicated that most of the title compounds showed good to excellent insecticidal activities against the oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). For the oriental armyworm, Ij displayed the same level of larvicidal activity as the positive control chlorantraniliprole, with an LC50 value of 0.21 mg/L. For the diamondback moth, In, Io, Ip, and Iq exhibited higher insecticidal activities than chlorantraniliprole. In particular, In had 50% larvicidal activity at 0.00001 mg/L. The calcium imaging technique was applied to study the effect of Ij, In, and Ip on the intracellular calcium ion concentration ([Ca2+]i) in central neurons isolated from the oriental armyworm. The results indicated that the tested compounds, such as chlorantraniliprole, could activate the insect RyRs. Furthermore, comparative molecular field analysis and density functional theory calculations were carried out to study the structure–activity relationship.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Synthesis, Insecticidal Evaluation, and 3D-QASR of Novel Anthranilic Diamide Derivatives Containing N-Arylpyrrole as Potential Ryanodine Receptor Activators

Wang

et al. 2020

J. Agric. Food Chem.

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“…The insecticidal activities of title compounds I-III against Mythimna separata were tested and are shown in Table 4. Title compounds I-III against Mythimna separata were determined in the greenhouse according to the reported method [37]. As shown in Table 4, most of them confirm good insecticidal activities at the concentration of 50 mg/L.…”

Section: Insecticidal Activity Against Mythimna Separata and Calcium mentioning

confidence: 99%

“…The insecticidal activity of I-III and chlorantraniliprole were tested by the reported method [37], and the result is shown in Table 4.…”

Section: Insecticidal Activity Against Mythimna Separatamentioning

confidence: 99%

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(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Liu

Gong

et al. 2019

Molecules

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A series of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a diacylhydrazine moiety were designed and synthesized. Their structures were confirmed by melting points, 1H NMR, 13C NMR, and elemental analysis (EA). Their antifungal and insecticidal activities were evaluated. The antifungal activity result indicated that most title compounds against Cercospora arachidicola, Alternaria solani, Phytophthora capsici, and Physalospora piricola exhibited apparent antifungal activities at 50 mg/L, and better than chlorothalonil or carbendazim. The EC50 values of (R)-N’-benzoyl-2-(4-chlorophenyl)-4,5-dihydrothiazole-4-carbohydrazide (I-5) against six tested phytopathogenic fungi were comparable to those of chlorothalonil. The CoMSIA model showed that a proper hydrophilic group in the R1 position, as well as a proper hydrophilic and electron-donating group in the R2 position, could improve the antifungal activity against Physalospora piricola, which contributed to the further optimization of the structures. Meanwhile, most title compounds displayed good insecticidal activities, especially compound (R)-N’-(4-nitrobenzoyl)-2-(4-nitrophenyl)-4,5-dihydrothiazole-4-carbohydrazide (III-3). The insecticidal mechanism results indicated that compound III-3 can serve as effective insect Ca2+ level modulators by disrupting the cellular calcium homeostasis in Mythimna separata.

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“…Therefore, diarylamines as easily available substrates have proven a convenient choice for construction of structural diversity molecules with promising bioactivity. In addition, carboxamides are also a useful class of molecules with potential pharmacological ( Odingo et al, 2017 ; Tang et al, 2018 ; Barker et al, 2019 ; Ling et al, 2019 ; Sethy et al, 2019 ; Sun et al, 2019 ; Yang et al, 2019 ) and agroactive activities ( Sartori et al, 2018 ; Tsikolia et al, 2018 ; Yu et al, 2018 ; Liu et al, 2019 ; Siber et al, 2019 ; Tsikolia et al, 2019 ; Liu et al, 2020 ), and many carboxamides have been developed as clinical drugs or agrochemicals, which demonstrate that amide units will play an important role in the development of drugs and pesticides.…”

Section: Introductionmentioning

confidence: 99%

Diarylamine-Guided Carboxamide Derivatives: Synthesis, Biological Evaluation, and Potential Mechanism of Action

Huang

Zhang

et al. 2022

Front. Chem.

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Diarylamines are a class of important skeleton widely existing in drugs or natural products. To discover novel diarylamine analogues as potential drugs, two series of diamide and carboxamide derivatives containing diarylamine scaffold were designed, synthesized and evaluated for their potential cytotoxic activities. The bioassay results indicated that some of the obtained compounds (C5, C6, C7, C11) exhibited good cytotoxic effect on cancer cell lines (SGC-7901, A875, HepG2), especially, compound C11 present significantly selective proliferation inhibition activity on cancer and normal cell lines (MARC145). In addition, the possible apoptosis induction for highly potential molecules was investigated, which present compound C11 could be used as novel lead compound for discovery of promising anticancer agents.

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Synthesis, insecticidal evaluation and 3D‐QSAR study of novel anthranilic diamide derivatives as potential ryanodine receptor modulators

Cited by 18 publications

References 25 publications

Synthesis, Insecticidal Evaluation, and 3D-QASR of Novel Anthranilic Diamide Derivatives Containing N-Arylpyrrole as Potential Ryanodine Receptor Activators

Synthesis, Insecticidal Evaluation, and 3D-QASR of Novel Anthranilic Diamide Derivatives Containing N-Arylpyrrole as Potential Ryanodine Receptor Activators

(R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Diarylamine-Guided Carboxamide Derivatives: Synthesis, Biological Evaluation, and Potential Mechanism of Action

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