N’-[(2,4-dimethoxyphenyl)methylidene]-4-methoxybenzohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N’-[(2,4-dimethoxyphenyl)methylidene]-4-methoxybenzohydrazide
• 英文别名: N-(4-methoxybenzoyl)-N'-(2,4-dimethoxybenzylidene)hydrazine；N-[(E)-(2,4-dimethoxyphenyl)methylideneamino]-4-methoxybenzamide
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: AKPIAVQYRMUSMC-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N’-[(2,4-dimethoxyphenyl)methylidene]-4-methoxybenzohydrazide 、 三苯基膦 、 palladium dichloride 在 LiCl 作用下， 以 甲醇 为溶剂， 以70%的产率得到[Pd(4-CH3OC6H4C(O)=NN=CH(2,4-(CH3O)2C6H2)(PPh3)]
  参考文献：
  名称：

  Synthesis, characterization and structural studies of palladium(II) complexes with N-(aroyl)-N′-(2,4-dimethoxybenzylidene)hydrazines

  摘要：

  Reactions of Li-2[PdCl4] with N-(aroyl)-N'-(2,4-dimethoxybenzylidene)hydrazines (H2L = (4-R-C6H4)C(=O)NHN=CH(2,4-(CH3O)(2)C6H3)) in presence of PPh3 have provided cyclopalladated complexes having the general formula [PdL(PPh3)] (1, 2 and 3 where R = OCH3, CH3 and Cl, respectively) and a coordination complex trans-[Pd(HL)(PPh3)(2)Cl] (4 where R = NO2). The complexes have been characterized by elemental analysis, infrared, H-1 NMR and electronic absorption spectroscopy. X-ray structures of all the complexes have been determined. In 1, 2 and 3, the C,N,O-donor dianionic ligand (L2-) forms two fused five-membered chelate rings at the metal centre. On the other hand, the monoanionic ligand (HL-) acts as deprotonated amide N-donor in 4. The strong electron withdrawing effect of the nitro group on the aroyl fragment is possibly responsible for the monodentate amide N-coordinating behavior of HL- in 4. The orientation of the 4-methoxy group in I is different than that in 2 and 3 due to intramolecular C-H...pi interaction in the last two complexes. The structure of 4 shows an apical C-H...Pd interaction involving the azomethine (-CH=N-) group of HL-. In the crystal lattice of all the structures, various types of intermolecular non-covalent interactions are present. The self-assembly of the molecules of 1, 2 and 3 leads to two-dimensional networks. The same network observed for 2 and 3 reflects the interchangeability of the chloro and methyl groups due to their similar volumes. In the case of 4, the complex and the water molecules present in the crystal lattice form parallel homo-chiral helices and finally interhelical interactions lead to a three-dimensional network. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.01.052
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 、 2,4-二甲氧基苯甲醛 以 乙醇 为溶剂， 以64%的产率得到N’-[(2,4-dimethoxyphenyl)methylidene]-4-methoxybenzohydrazide
  参考文献：
  名称：

  葡萄糖反应性胰岛素的醛类反应性，可裂解连接子

  摘要：

  对血糖浓度变化有反应的葡萄糖反应性胰岛素（GRI）仍然是一个遥不可及的目标。在这里，我们描述了基于和噻唑烷结构的葡萄糖可裂解接头的发展。我们开发了具有低自发水解水平的连接子，但是随着葡萄糖浓度的升高，水解水平增加，这表明了它们在体外的葡萄糖响应性。通过pH控制的酰化作用将脂化和噻唑烷偶联到HI的LysB29侧链上，从而为GRI提供体外已证实的噻唑烷葡萄糖反应性。钳位研究显示，在高血糖条件下，对于一种GRI的葡萄糖输注增加，这表明了真正的葡萄糖反应。这些GRI中的葡萄糖反应性可裂解连接子允许葡萄糖水平发生变化，以驱动活性胰岛素从循环库释放。我们已经证明了生物制药领域前所未有的，具有化学响应能力的接头概念。

  DOI：

  10.1002/chem.202004878

文献信息

• An Aldehyde Responsive, Cleavable Linker for Glucose Responsive Insulins
  作者：Karin Mannerstedt、Narendra Kumar Mishra、Ebbe Engholm、Morten Lundh、Charlotte S. Madsen、Philip J. Pedersen、Priska Le‐Huu、Søren L. Pedersen、Nina Buch‐Månson、Björn Borgström、Thomas Brimert、Lisbeth N. Fink、Keld Fosgerau、Niels Vrang、Knud J. Jensen

  DOI：10.1002/chem.202004878

  日期：2021.2.10

  by pH‐controlled acylations providing GRIs with glucose responsiveness confirmed in vitro for thiazolidines. Clamp studies showed increased glucose infusion at hyperglycemic conditions for one GRI indicative of a true glucose response. The glucose responsive cleavable linker in these GRIs allow changes in glucose levels to drive the release of active insulin from a circulating depot. We have demonstrated

  对血糖浓度变化有反应的葡萄糖反应性胰岛素（GRI）仍然是一个遥不可及的目标。在这里，我们描述了基于和噻唑烷结构的葡萄糖可裂解接头的发展。我们开发了具有低自发水解水平的连接子，但是随着葡萄糖浓度的升高，水解水平增加，这表明了它们在体外的葡萄糖响应性。通过pH控制的酰化作用将脂化和噻唑烷偶联到HI的LysB29侧链上，从而为GRI提供体外已证实的噻唑烷葡萄糖反应性。钳位研究显示，在高血糖条件下，对于一种GRI的葡萄糖输注增加，这表明了真正的葡萄糖反应。这些GRI中的葡萄糖反应性可裂解连接子允许葡萄糖水平发生变化，以驱动活性胰岛素从循环库释放。我们已经证明了生物制药领域前所未有的，具有化学响应能力的接头概念。
• Synthesis, characterization and structural studies of palladium(II) complexes with N-(aroyl)-N′-(2,4-dimethoxybenzylidene)hydrazines
  作者：Sunirban Das、Samudranil Pal

  DOI：10.1016/j.jorganchem.2006.01.052

  日期：2006.5

  Reactions of Li-2[PdCl4] with N-(aroyl)-N'-(2,4-dimethoxybenzylidene)hydrazines (H2L = (4-R-C6H4)C(=O)NHN=CH(2,4-(CH3O)(2)C6H3)) in presence of PPh3 have provided cyclopalladated complexes having the general formula [PdL(PPh3)] (1, 2 and 3 where R = OCH3, CH3 and Cl, respectively) and a coordination complex trans-[Pd(HL)(PPh3)(2)Cl] (4 where R = NO2). The complexes have been characterized by elemental analysis, infrared, H-1 NMR and electronic absorption spectroscopy. X-ray structures of all the complexes have been determined. In 1, 2 and 3, the C,N,O-donor dianionic ligand (L2-) forms two fused five-membered chelate rings at the metal centre. On the other hand, the monoanionic ligand (HL-) acts as deprotonated amide N-donor in 4. The strong electron withdrawing effect of the nitro group on the aroyl fragment is possibly responsible for the monodentate amide N-coordinating behavior of HL- in 4. The orientation of the 4-methoxy group in I is different than that in 2 and 3 due to intramolecular C-H...pi interaction in the last two complexes. The structure of 4 shows an apical C-H...Pd interaction involving the azomethine (-CH=N-) group of HL-. In the crystal lattice of all the structures, various types of intermolecular non-covalent interactions are present. The self-assembly of the molecules of 1, 2 and 3 leads to two-dimensional networks. The same network observed for 2 and 3 reflects the interchangeability of the chloro and methyl groups due to their similar volumes. In the case of 4, the complex and the water molecules present in the crystal lattice form parallel homo-chiral helices and finally interhelical interactions lead to a three-dimensional network. (c) 2006 Elsevier B.V. All rights reserved.