1H-Isoindole-1,3(2H)-dione, 2-[(4-methylphenyl)methyl]-5-nitro- | 89024-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1H-Isoindole-1,3(2H)-dione, 2-[(4-methylphenyl)methyl]-5-nitro-
• 英文别名: 2-[(4-methylphenyl)methyl]-5-nitroisoindole-1,3-dione
• CAS: 89024-38-4
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: DERNHTHLGVUITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1H-Isoindole-1,3(2H)-dione, 2-[(4-methylphenyl)methyl]-5-nitro- 在 N-甲基咪唑 、 铁粉 、 氯化铵 、 N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 3-bromo-1-(3-chloropyridin-2-yl)-N-(2-(4-methylbenzyl)-1,3-dioxoisoindolin-5-yl)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and 3D-QASR of N-Pyridylpyrazole Amide Derivatives Containing a Phthalimide as Potential Ryanodine Receptor Activators

  摘要：

  To develop potent and environment-friendly insecticides, novel N-pyridylpyrazole amide derivatives containing a phthalimide were designed and synthesized. The preliminary bioassay results showed that most of the target compounds exhibited good insecticidal activities. For oriental armyworm (Mythimna separata), compounds E5, E29, E30, and E33 displayed higher than 90% lethal rates at 25 mg L-1. In particular, compound E33 displayed 60% mortality at a lower concentration of 6.25 mg L-1. Besides, compound E33 also showed a 30% lethal rate at 5 mg L-1 against diamondback moth (DBM) (Plutella xylostella). Molecular docking between the most active compound E33 and DBM ryanodine receptor (RyR), comparative molecular field analysis (CoMFA), and density functional theory (DFT) calculations were conducted and discussed. Furthermore, according to vitro studies using a calcium imaging technique, compound E33 was a potent novel lead targeting insect RyR.

  DOI：

  10.1021/acs.jafc.2c03971
• 作为产物：
  描述：

  4-硝基邻苯二甲酸酐 、 4-甲基苄胺 在 溶剂黄146 作用下， 生成 1H-Isoindole-1,3(2H)-dione, 2-[(4-methylphenyl)methyl]-5-nitro-
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and 3D-QASR of N-Pyridylpyrazole Amide Derivatives Containing a Phthalimide as Potential Ryanodine Receptor Activators

  摘要：

  To develop potent and environment-friendly insecticides, novel N-pyridylpyrazole amide derivatives containing a phthalimide were designed and synthesized. The preliminary bioassay results showed that most of the target compounds exhibited good insecticidal activities. For oriental armyworm (Mythimna separata), compounds E5, E29, E30, and E33 displayed higher than 90% lethal rates at 25 mg L-1. In particular, compound E33 displayed 60% mortality at a lower concentration of 6.25 mg L-1. Besides, compound E33 also showed a 30% lethal rate at 5 mg L-1 against diamondback moth (DBM) (Plutella xylostella). Molecular docking between the most active compound E33 and DBM ryanodine receptor (RyR), comparative molecular field analysis (CoMFA), and density functional theory (DFT) calculations were conducted and discussed. Furthermore, according to vitro studies using a calcium imaging technique, compound E33 was a potent novel lead targeting insect RyR.

  DOI：

  10.1021/acs.jafc.2c03971