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合成、杀虫剂评价及部分新功能化吡唑衍生物对棉铃虫(Spodoptera littoralis)的分子对接研究。

Synthesis, Insecticide Evaluation & Molecular Docking Studies of Some New Functionalized Pyrazole Derivatives Against the Cotton Leafworm, Spodoptera littoralis.

机构信息

Department of Chemistry, Faculty of Science, Al-Azhar University at Assiut, 71524, Assiut, Egypt.

Chemistry Department, Faculty of Science, Sohag University, 282524, Sohag, Egypt.

出版信息

Chem Biodivers. 2024 Oct;21(10):e202400831. doi: 10.1002/cbdv.202400831. Epub 2024 Sep 11.

Abstract

5-(Cyanomethyl)-3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino)-1H-pyrazole-4-carbonitrile (3) is used as a key for the synthesis of arylidenes 5 a-fvia its reaction with some aldehydes 4 a-f. 5-[(5,5-Dimethyl-3-oxocyclohex-1-en-1-yl)amino]-3-(2-imino-2H-chromen-3-yl)-1H-pyrazole-4-carbonitrile (7) was synthesized via the reaction of compound (3) with 2-Hydroxybenzaldehyde in EtOH/piperidine. The target compounds were tested against cotton leafworm larvae in their second and fourth instar. The available data demonstrated that the LC values for commercial phenylpyrazole were 3.37 mg/L and 4.55 mg/L for the most affected synthesized compound, 5 b. The chemical structure of compound 5 bhas two cyano moieties, a pyrazole ring and a chlorophenyl, which may be increasing it efficiency. Evaluation of the latent effects of the examined synthesized compounds on various biological parameters, including adult longevity, pupal weight, proportion of normal, deformed pupae, adult emergency, fecundity, and egg hatchability, was done in an additional effort to slightly improve insecticidal compounds. Seven target synthesized compounds were subjected to a molecular docking analysis against glutamate-activated chloride channels. Twelve artificial compounds with the PDB ID of 4COF were subjected to a molecular docking study against the gamma-aminobutyric acid receptor (GABA).

摘要

5-(氰甲基)-3-((5,5-二甲基-3-氧代环己-1-烯-1-基)氨基)-1H-吡唑-4-甲腈(3)用作合成芳基亚乙烯基化合物 5 a-f 的关键,方法是与一些醛 4 a-f 反应。5-[(5,5-二甲基-3-氧代环己-1-烯-1-基)氨基]-3-(2-亚氨基-2H-色烯-3-基)-1H-吡唑-4-甲腈(7)通过化合物(3)与 2-羟基苯甲醛在 EtOH/哌啶中的反应合成。目标化合物在第二和第四龄期棉铃虫幼虫中进行了测试。现有数据表明,商业苯基吡唑的 LC 值为 3.37mg/L 和 4.55mg/L,对受影响最大的合成化合物 5 b 而言。化合物 5 b 的化学结构有两个氰基部分、一个吡唑环和一个氯苯基,这可能使其效率提高。为了略微提高杀虫化合物的效果,还评估了所研究的合成化合物对各种生物参数的潜在影响,包括成虫寿命、蛹重、正常、畸形蛹的比例、成虫紧急情况、繁殖力和卵孵化率。七种目标合成化合物进行了分子对接分析,以研究其对谷氨酸激活氯离子通道的影响。十二种具有 PDB ID 为 4COF 的人工化合物进行了分子对接研究,以研究其对γ-氨基丁酸受体(GABA)的影响。

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