2,6-bis[(4-hydroxyphenylamino)methylene]pyridine | 219561-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-bis[(4-hydroxyphenylamino)methylene]pyridine
• 英文别名: 2,6-pyridinedicarboxaldehyde bis(p-hydroxyphenylimine)；4,4a(2)-[2,6-Pyridinediylbis(methylidynenitrilo)]bis[phenol]；4-[[6-[(4-hydroxyphenyl)iminomethyl]pyridin-2-yl]methylideneamino]phenol
• CAS: 219561-19-0
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: MSTIVGRNWPKULM-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C
• 沸点：
  608.1±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis[(4-hydroxyphenylamino)methylene]pyridine 以 乙醇 为溶剂， 生成 [Ni(2,6-pyridinedicarboxaldehydebis(p-hydroxyphenylimine))Cl2]
  参考文献：
  名称：

  Synthesis, characterization and biological activity of bis(phenylimine) Schiff base ligands and their metal complexes

  摘要：

  Metal complexes derived from 2,6-pyridinedicarboxaldehydebis(p-hydroxyphenylimine); L-1, 2,6-pyfidinedicarboxaldehydebis (o-hydroxyphenylimine); L-2, are reported and characterized based on elemental analyses, IR, solid reflectance, magnetic moment, molar conductance and thermal analysis (TGA). The complexes are found to have the formulae [MX2(L-1 or L-2)](.)nH(2)O, where M = Fe(II), Co(II), Ni(II), Cu(II) and Zn(II), X = Cl in case of Fe(II), Co(II), Ni(II), Cu(II) complexes and Br in case of Zn(II) complexes and n = 0-2.5. The molar conductance data reveal that the chelates are non-electrolytes. IR spectra show that the Schiff bases are coordinated to the metal ions in a terdentate manner with NNN donor sites of the pyridine-N and two azomethine-N. From the magnetic and solid reflectance spectra, it is found that the geometrical structure of these complexes are trigonal bipyramidal (in case of Co(II), Ni(II), Cu(II) and Zn(II) complexes) and octahedral (in case of Fe(II) complexes). The thermal behaviour of these chelates shows that the hydrated complexes losses water molecules of hydration in the first step followed immediately by decomposition of the coordinated water, anions and ligands (L-1 and L-2) in the subsequent steps. The activation thermodynamic parameters, such as, E*, Delta H*, Delta S* and Delta G* are calculated from the TG curves using Coats-Redfern method. The synthesized ligands, in comparison to their metal complexes also were screened for their antibacterial activity against bacterial species, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Fungi (Candida). The activity data show that the metal complexes to be more potent/antibacterial than the parent organic ligands against one or more bacterial species. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2005.05.044
• 作为产物：
  描述：

  吡啶-2,6-二甲醛 、 对氨基苯酚 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到2,6-bis[(4-hydroxyphenylamino)methylene]pyridine
  参考文献：
  名称：

  双（亚氨基）吡啶作为抗氧化剂，乙酰胆碱酯酶抑制剂和抗菌剂的合成，表征和SAR研究。

  摘要：

  在这项研究中，我们从2，6-二氨基吡啶和各种芳香醛开始合成了16种双（亚氨基）吡啶（BIP），并评估了它们的抗氧化，抗菌，抗真菌和乙酰胆碱酯酶（AChE）抑制活性。通过FTIR，元素分析，ESR和HRMS阐明了化学结构。ESR光谱法和DFT计算证实，由于在溶液中形成了稳定的，以碳为中心的自由基阳离子，因此无法获得1 H和13 C NMR光谱。在体外使用四种测定法评估抗氧化剂效能：自由基清除活性（DPPH和ABTS），还原能力和总抗氧化剂容量测定法。BIP具有出色的抗氧化剂性能，并且在所有测定中，两种衍生物均被证明比参考抗氧化剂（抗坏血酸和Trolox）更有效。在ωB97XD/ 6-311 ++ g（d，p）水平上的DFT计算为BIP的自由基清除机理提供了有价值的见解。对于羟基取代的BIP，氢原子转移（HAT）是主要机制，而单电子转移与质子转移（SET-PT）结合则决定了其他衍生物的抗氧化活

  DOI：

  10.1016/j.bioorg.2020.104073

文献信息

• Constitutional self-sorting of homochiral supramolecular helical single crystals from achiral components
  作者：Florina Dumitru、Yves-Marie Legrand、Arie Van der Lee、Mihail Barboiu

  DOI：10.1039/b822619a

  日期：——

  Double-helical architectures obtained from achiral ligands and metal ions present supramolecular homochirality in the single -crystal state under constitutional self-sorting.

  由非手性配体和金属离子形成的双螺旋结构在单晶状态下呈现超分子同手性，这是构象自排序的结果。
• Self-sorting of metallosupramolecular DCLs via double-level exchange: amplification in solution and solid state modulation
  作者：Florina Dumitru、Yves-Marie Legrand、Eddy Petit、Arie van der Lee、Mihail Barboiu

  DOI：10.1039/c2dt31532g

  日期：——

  Interexchanging metallosupramolecular double level imine/ligand Dynamic Constitutional Libraries (DCLs), produce, in solution, the amplification of heteroleptic complexes, which convert into homoleptic complexes via constitutional crystallization.

  互变金属超分子双级亚胺/配体动态构象库（DCL）在溶液中产生放大的异色复合物，并通过构象结晶转化为同色复合物。
• Self-sorting of equilibrating metallosupramolecular DCLs via constitutional crystallization
  作者：Mihail Barboiu、Florina Dumitru、Yves-Marie Legrand、Eddy Petit、Arie van der Lee

  DOI：10.1039/b900155g

  日期：——

  Zn2+ and Pb2+ and ligands 1 and 2 self-assemble in solution to generate DCLs of interexchanging metallosupramolecular subcomponents, which convert into robust species of unique stoichiometry via constitutional crystallization.

  Zn2+和Pb2+以及配体1和2在溶液中自组装，形成可相互交换的金属超分子亚组分的DCL，通过构象结晶转化为具有独特化学计量比的稳定物质。
• Mixed ligand complexes of bis(phenylimine) Schiff base ligands incorporating pyridinium moiety
  作者：Gehad G. Mohamed、Zeinab H. Abd El-Wahab

  DOI：10.1016/j.saa.2004.06.021

  日期：2005.4

  The synthesis and structural characterization of mixed ligand complexes derived from 2,6-pyridinedicarboxaldehydebis(o-hydroxyphenylirnine) 2 6-pN,ridinedicarboxaldehydebis(1(ry)-hydroxyphenylimine) (2(ry) ligands) and 2-aminopyridne (2ry ligand) are reported. The ligands and their transition metal complexes were characterized on the bases of their elemental analyses, IR, solid reflectance, magnetic moment, molar conductance and thermal analysis (TGA). The mixed ligand complexes are formed in the 1: 1: 1 (M:L-1 or L-2 :L') ratio as found from the elemental analyses and found to have the formulae [MX2(L-1 or L-2)(L')](.)nH(2)O where M = Co(II), Ni(II), Cu(II) and Zn(II), L' = (2,6-pyridinedicarboxaldehydebis(p-hydroxyphenylimine), L-2 = 2,6-pyridine dicarboxaldehydebis(o-hydroxyphenylimine), L'= 2-aminopyridine, X = Cl- in case of Cu(II) complex and Br- in case of Co(II), Ni(II) and Zn(II) complexes and y = 0-3. The molar conductance data reveal that the chelates are non-electrolytes. IR spectra show that the Schiff bases are coordinated to the metal ions in a terdentate manner with NNN donor sites of the pyridine-N and two azomethine-N. While 2-aminopyridine coordinated to the metal ions via its pyridine-N. Magnetic and solid reflectance spectra are used to infer the coordinating capacity of the ligand and the geometrical structure of these complexes are found to be octahedral. The thermal behaviour of these chelates shows that the hydrated water molecules and the anions are removed in a successive two steps followed immediately by decomposition of the ligands (L', L-2 and L') in the subsequent steps. The activation thermodynamic parameters, such as. E*, Delta H*. Delta S* and Delta G* are calculated from the TG curves and discussed. The ligands and their metal chelates have been screened for their antimicrobial activities and the findings have been reported, explained and compared with some known antibiotics. (c) 2004 Elsevier B.V. All rights reserved.