2-(4'-aminophthalimidomethyl)pyridine | 795297-17-5

• 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: 2-(4'-aminophthalimidomethyl)pyridine
• 英文别名: 5-Amino-2-(pyridin-2-ylmethyl)isoindole-1,3-dione
• CAS: 795297-17-5
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: IEOLQZRBEANHHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴-1-(3-氯-2-吡啶)-1H-吡唑-5-羧酸 、 2-(4'-aminophthalimidomethyl)pyridine 在 N-甲基咪唑 、 N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 以80%的产率得到3-bromo-1-(3-chloropyridin-2-yl)-N-(2-(pyridin-2-ylmethyl)-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：

  2-氨甲基吡啶 在 铁粉 、 氯化铵 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-(4'-aminophthalimidomethyl)pyridine
  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

文献信息

• In Situ Reduction of Copper(II) Forming an Unusually Air Stable Linear Complex of Copper(I) with a Fluorescent Tag
  作者：Sandip Banthia、Anunay Samanta

  DOI：10.1021/ic0490019

  日期：2004.11.1

  A new fluorescent ligand (phi(f) = 0.8 in dioxane), 2-(4'-aminophthalimidomethyl)pyridine (L), has been synthesized. A one-pot synthesis of its copper(I) complex upon reduction of copper(II) is achieved at room temperature. This complex, which has been characterized by X-ray crystallography, shows a linear N-Cu-N geometry with Cu-N bond lengths of 1.89 Angstrom. X-ray structure reveals weak (CuO)-O-... interactions between copper and one of the imide oxygen atoms of the ligand framework. Additional weak (CuO)-O-... interactions between copper and oxygen atoms of the CIO4- counteranion are detected that lead to a zigzag polymeric chain with alternate CIO4- and copper ions. A 2-D intermolecular hydrogen bonding network is also observed. This complex is found to be highly inert toward oxidation both in the solid state and in solution.
• Synthesis and structure of unusually stable linear copper(I) complexes with blue fluorescence
  作者：Sandip Banthia、Anunay Samanta

  DOI：10.1016/j.poly.2006.01.025

  日期：2006.7

  A new fluorescent ligand 2-(4-aminophthalimidoethyl)pyridine (L-2) has been synthesized. Solid state structures of L-2 and 2-(4'-aminophthalimidomethyl)pyridine (L-1) have been determined by X-ray crystallography. While L-1 crystallizes in the non-centrosymmetric orthorhombic space group Fdd2, L-2 crystallizes in the monoclinic space group C2/c. The molecular packing in both systems is dominated by intermolecular N-H center dot center dot center dot O and N-H center dot center dot center dot N hydrogen bonds and relative bending of the planes defined by the pyridine and phthalimide moieties. An unusually stable two-coordinate complex of copper(I) with L-2, Cu(L-2)(2), has been synthesized upon in situ reduction of copper(II) at room temperature. This complex, which has been characterized by X-ray crystallography, crystallizes in the centrosymmetric space group C2/c with a linear N-Cu-N geometry. The Cu-N bond distance (1.89 angstrom) in Cu(L-2)(2) is found to be similar to that in Cu(L-1)(2). Both the complexes display interesting structural feature, arising from weak Cu center dot center dot center dot O interactions (3.12 angstrom in Cu(L-1)(2) and 2.71 angstrom in Cu(L-2)(2)) between the copper and oxygen atoms of the ClO4- counteranion, leading to a linear network with alternate ClO4- and Cu+ ions. A 2-D network determined by intermolecular N-H center dot center dot center dot O hydrogen bonding is also observed. These complexes are found to be highly resistant toward oxidation both in the solid state and in solution. The new complex Cu(L-2)(2), in which the metal center is more separated from the 4-aminophthalimide moieties, exhibits lesser stability than Cu(L-1)(2). Close contact between copper and one of the imide oxygen atoms of the ligand framework was detected as 3.03 angstrom in Cu(L-1)(2) and 4.0 angstrom in Cu(L-2)(2), indicating a relatively weaker electronic interaction in the later complex. Thus, the exceptional stability of these complexes is attributed to the electronic environment provided by the 4-aminophthalimide and perchlorate moieties on the metal center. (C) 2006 Elsevier Ltd. All rights reserved.