Synthesis and Biological Activity Evaluation of Novel Chalcone Analogues Containing a Methylxanthine Moiety and Their <i>N</i>-Acyl Pyrazoline Derivatives

Wang, Lei; Fan, Wenqi; Cui, Li; Yang, Na; Zhang, Xiao; Yu, Shujing; Li, Yonghong; Wang, Baolei

doi:10.1021/acs.jafc.3c05008

Cited by 3 publications

(1 citation statement)

References 46 publications

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“…The insecticidal activities of compounds 4.3 , 6.3 – 6.6 , 6.16 , 6.17 , and 6.19 were evaluated against the third-instar larvae of P. xylostella starved for 4 h using the leaf-dipping method, as described in the literature. , All target compounds were dissolved in DMSO and diluted to the test concentration with a 0.5‰ aqueous solution of Tween-80. The cabbage leaves were dipped in each test solution for 30 s. After air drying, the treated leaves were placed in Petri dishes (diameter of 9 cm), and 10 third-instar larvae of P.…”

Section: Methodsmentioning

confidence: 99%

In-Depth Structural Simplification of Celangulin V: Design, Synthesis, and Biological Activity

Qian,

Hu,

Wang

et al. 2024

J. Agric. Food Chem.

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Celangulin V is a novel botanical insecticide with significant bioactivity and a unique molecular target, but its complex polyol ester structure hinders its broader application in agriculture. To discover new analogues of celangulin V with a simpler structure and enhanced biological activities, we initiated a research project aimed at simplifying its structure and assessing insecticidal efficacy. In this study, a series of novel 1-tetralone derivatives were designed via a structure-based rational design approach and synthesized by a facile method. The biological activities of the target compounds were determined against Mythimna separata (M. separata), Plutella xylostella, and Rhopalosiphum padi. The results revealed that most of the synthesized compounds exhibited superior activities compared to celangulin V. Remarkably, the insecticidal activity of compound 6.16 demonstrated 102-fold greater stomach toxicity than celangulin V against M. separata. In addition, certain compounds showed significant contact toxicity against M. separata, a finding not reported previously in the structural optimization studies of celangulin V. Molecular docking analysis illustrated that the binding pocket of compound 6.16 with the H subunit of V-ATPase was the same as celangulin V. This study presents novel insights into the structural optimization of botanical pesticides.

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Section: Methodsmentioning

confidence: 99%

In-Depth Structural Simplification of Celangulin V: Design, Synthesis, and Biological Activity

Qian,

Hu,

Wang

et al. 2024

J. Agric. Food Chem.

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Synthesis and Fungicidal Activity Evaluation of Novel Triazole Thione/Thioether Derivatives Containing a Pyridylpyrazole Moiety

Fan,

Huang,

et al. 2024

Chemistry & Biodiversity

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Compounds containing N‐pyridylpyrazole motif have aroused interest and brought about research hotspots due to their highly‐efficient insecticidal activity. The fungicidal potential of N‐pyridylpyrazole derivatives has gradually been disclosed in recent years. To discover new agrochemicals with poly‐heterocyclic features, a series of novel triazole thione/thioether derivatives containing pyridylpyrazole motif (8‐11) was synthesized. The new compounds were identified by melting point, 1H NMR, 13C NMR, 19F NMR, HRMS, and elemental analysis. The bioassays showed that most of the pyridylpyrazole‐containing triazole thione Mannich bases possessed favorable in vitro fungicidal activity toward pathogenic fungi, such as Magnaporthe oryzae, Sclerotinia sclerotiorum, Botrytis cinerea and Fusarium verticillioides, and were comparable with those of the contrast compounds A and triadimefon. Some of them exhibited moderate to good in vivo fungicidal activity against S. sclerotiorum at 0.2 mg/mL (e.g. 8f control efficacy: 60.9±3.2%). The SEM observation displayed that 8f might cause disruption of cell membrane and wall of S. sclerotiorum. Compounds 8a, 8c, 8f‐8h, 8p and 9b can serve as promising new fungicidal agents to make further structural optimization. The findings in this article provide useful clue and guidance for the design and development of new poly‐heterocyclic agrochemicals.

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Studies on the synthesis, crystal structures, biological activities and molecular docking of novel natural methylxanthine derivatives containing piperazine moiety

Fan,

Zhang,

Yang

et al. 2024

Mol Divers

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Synthesis and Biological Activity Evaluation of Novel Chalcone Analogues Containing a Methylxanthine Moiety and Their N-Acyl Pyrazoline Derivatives

Cited by 3 publications

References 46 publications

In-Depth Structural Simplification of Celangulin V: Design, Synthesis, and Biological Activity

In-Depth Structural Simplification of Celangulin V: Design, Synthesis, and Biological Activity

Synthesis and Fungicidal Activity Evaluation of Novel Triazole Thione/Thioether Derivatives Containing a Pyridylpyrazole Moiety

Studies on the synthesis, crystal structures, biological activities and molecular docking of novel natural methylxanthine derivatives containing piperazine moiety

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