2,6-bis(2-hydroxyphenyliminomethyl)pyridine | 1823-48-9

• 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(2-hydroxyphenyliminomethyl)pyridine
• 英文别名: N,N-(2,6-pyridinediyldimethylidyne)bis(2-hydroxybenzenamine)；2,2a(2)-[2,6-Pyridinediylbis(methylidynenitrilo)]bis[phenol]；2-[[6-[(2-hydroxyphenyl)iminomethyl]pyridin-2-yl]methylideneamino]phenol
• CAS: 1823-48-9
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: BKQAGXBRRSLMGI-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °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(2-hydroxyphenyliminomethyl)pyridine 以 乙醇 为溶剂， 生成 [Co(2,6-pyridinedicarboxaldehydebis(o-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-2,6-二甲酸 在 selenium(IV) oxide 、 sodium tetrahydroborate 、 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 2,6-bis(2-hydroxyphenyliminomethyl)pyridine
  参考文献：
  名称：

  新型吡啶席夫碱锰（ii）配合物：环己烯环氧化的合成，表征和催化反应性

  摘要：

  四个新颖的​​吡啶席夫碱衍生自 2,6-吡啶二甲醛并通过元素分析，ESI-MS分析，热分析（TGA），1 H-NMR，IR和UV-vis对合成的和取代的邻-羟基-芳族胺及其锰（II）配合物进行了表征。研究了这些络合物在环己烯自氧化反应中作为催化剂的活性，并优化了各种反应条件对催化反应的影响，从而获得了高达99.6％的转化率和95.0％的选择性。环氧环己烷 在40°C下使用分子氧作为氧化剂6小时 乙腈。结果为环戊烷的环氧化提供了极好的催化剂环己烯在温和的温度和大气氧（O 2）压力下。

  DOI：

  10.1039/c3ra40398j

文献信息

• Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents
  作者：Milena D. Milošević、Aleksandar D. Marinković、Predrag Petrović、Anita Klaus、Milica G. Nikolić、Nevena Ž. Prlainović、Ilija N. Cvijetić

  DOI：10.1016/j.bioorg.2020.104073

  日期：2020.9

  assays: free radical scavenging activity (DPPH and ABTS), reducing power and total antioxidant capacity assay. BIPs demonstrated excellent antioxidant properties, and two derivatives proved to be more potent than reference antioxidants (ascorbic acid and Trolox) in all assays. DFT calculations on ωB97XD/6-311++g(d,p) level of theory provided valuable insights into the radical scavenging mechanism of BIPs

  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
• Heptacoordinate Tin(IV) Compounds Derived from Pyridine Schiff Bases: Synthesis, Characterization, in Vitro Cytotoxicity, Anti-inflammatory and Antioxidant Activity
  作者：Arturo González、Elizabeth Gómez、Armando Cortés-Lozada、Simón Hernández、Teresa Ramírez-Apan、Antonio Nieto-Camacho

  DOI：10.1248/cpb.57.5

  日期：——

  Tin(IV) complexes 2a—q derived from pyridine Schiff bases were prepared and characterized. Four complexes of this series were evaluated in vitro against different carcinogenic cell lines; besides their anti-inflammatory and antioxidant properties were also tested. Combination of mass spectrometry, multinuclear NMR and X-ray diffraction techniques evidenced the formation of heptacoordinated monomeric species. The X-ray diffraction analysis of 2a, 2b, 2i, 2j and 2n led to establish the heptacoordination around the tin atom in solid state and also revealed that the ligand occupies the equatorial positions of the distorted pentagonal bipyramidal geometry and the two alkyl or aryl groups the axial positions. The in-vitro study for complexes 2a—d against six tumor cell lines showed varied antiproliferative activity, the IC50 for all tested complexes was lower than that of the cis-platin. Compounds 2a—d also exhibited anti-inflammatory activity where complex 2c resulted to be more active (IC50=0.11 μM) than the indomethacin IC50=0.27 μM which was used as reference. The antioxidant activity in rat brain homogenate on inhibition of thiobarbituric acid reactive substances (TBARS) indicated that 2c (IC50=1.77 μM) is more active than the quercetine (4.11 μM) and α-tocopherol (IC50=569.09 μM).

  研究人员制备了由吡啶席夫碱衍生的锡（IV）配合物 2a-q，并对其进行了表征。该系列的四种配合物针对不同的致癌细胞系进行了体外评估；此外，还测试了它们的抗炎和抗氧化特性。质谱、多核核磁共振和 X 射线衍射技术的结合证明了七配位单体的形成。通过对 2a、2b、2i、2j 和 2n 的 X 射线衍射分析，确定了固态锡原子周围的七配位，还发现配体占据了扭曲五边形双锥几何的赤道位置，而两个烷基或芳基则占据了轴向位置。复合物 2a-d 对六种肿瘤细胞株的体外研究显示了不同的抗增殖活性，所有测试复合物的 IC50 均低于顺铂。复合物 2a-d 还具有抗炎活性，其中复合物 2c 的活性（IC50=0.11 μM）高于用作参考的吲哚美辛 IC50=0.27 μM。大鼠脑匀浆中抑制硫代巴比妥酸活性物质（TBARS）的抗氧化活性表明，2c（IC50=1.77 μM）的活性高于槲皮素（4.11 μM）和α-生育酚（IC50=569.09 μM）。
• Novel pyridine Schiff base–manganese(ii) complexes: synthesis, characterization and catalytic reactivity of the epoxidation of cyclohexene
  作者：Zhongying Li、Changhui Liu、Ruiren Tang、Guiyin Liu

  DOI：10.1039/c3ra40398j

  日期：——

  o-hydroxyl-aromatic amines and their manganese(II) complexes were synthesized and characterized by elemental analyses, ESI-MS analysis, thermal analysis (TGA), H-NMR, IR and UV-vis. The activity of these complexes as catalysts in cyclohexene autoxidation were investigated and the effects of various reaction conditions on the catalytic reaction were optimized to obtain as high as 99.6% conversion with 95.0% selectivity

  四个新颖的​​吡啶席夫碱衍生自 2,6-吡啶二甲醛并通过元素分析，ESI-MS分析，热分析（TGA），1 H-NMR，IR和UV-vis对合成的和取代的邻-羟基-芳族胺及其锰（II）配合物进行了表征。研究了这些络合物在环己烯自氧化反应中作为催化剂的活性，并优化了各种反应条件对催化反应的影响，从而获得了高达99.6％的转化率和95.0％的选择性。环氧环己烷 在40°C下使用分子氧作为氧化剂6小时 乙腈。结果为环戊烷的环氧化提供了极好的催化剂环己烯在温和的温度和大气氧（O 2）压力下。
• Synthesis and Magnetic Properties of Two‐Step‐Coordination Schiff Base Clusters
  作者：Laurens C. J. M. Peters、Hans Engelkamp、Uli Zeitler、Peter C. M. Christianen、Paul Tinnemans、Jan‐Kees Maan、Alan E. Rowan

  DOI：10.1002/ejic.202100298

  日期：2021.7.15

  A new family of paramagnetic coordination compounds based on a diimine-pyridine pincer ligand has been prepared, using a two-step synthetic approach. The sequential introduction of identical or different transition metals (Co, Mn, Ni, Zn) afforded mono-, di-, tri- and tetranuclear clusters, whose crystal structure has been determined. Magnetic studies reveal that the metals within the trinuclear manganese

  使用两步合成方法制备了基于二亚胺-吡啶钳形配体的新系列顺磁性配位化合物。连续引入相同或不同的过渡金属（Co、Mn、Ni、Zn）可提供单核、双核、三核和四核簇，其晶体结构已确定。磁学研究表明，三核锰簇内的金属进行小的铁磁交换相互作用 ( J = 0.15 K)。这些研究使设计具有特定磁性的新簇成为可能。
• Dysprosium-based complexes with a flat pentadentate donor: a magnetic and <i>ab initio</i> study
  作者：Matilde Fondo、Julio Corredoira-Vázquez、Ana M. García-Deibe、Silvia Gómez-Coca、Eliseo Ruiz、Jesús Sanmartín-Matalobos

  DOI：10.1039/d0dt01293a

  日期：——

  The reactivity of the well-known pentadentate N3O2 Schiff base H2L (2,6-bis(2-hydroxyphenyliminomethyl)pyridine) towards a lanthanoid metal, in this case DyIII, has been investigated for the first time. This reactivity markedly depends on the pH of the medium and, accordingly, two different complexes, [Dy(HL)(NO3)2]·H2O (1·H2O) and [Dy(L)(NO3)(EtOH)(H2O)]·2H2O (2·2H2O), could be isolated from dysprosium(III)

  首次研究了众所周知的五齿N 3 O 2 Schiff碱H 2 L（2,6-双（2-羟基苯基亚氨基甲基）吡啶）对镧系金属（在此情况下为Dy III）的反应性。该反应性明显取决于介质的pH，因此取决于两种不同的络合物，[Dy（HL）（NO 3）2 ]·H 2 O（1 ·H 2 O）和[Dy（L）（NO 3） （EtOH）（H 2 O）]·2H 2 O（2 ·2H 2 O）可以从硝酸（（III）和H 2中分离出来L.此外，H 2 L与氯化（III）在甲醇中的反应生成[Dy（HL'）2 ] [Dy（L）（Cl 2）]（3），其中H 2 L'（（6- （2-羟基苯基亚氨基甲基）-2-甲氧基羟基甲基）吡啶）是N 2 O 2半缩醛供体，其衍生自H 2 L配体的部分水解，然后将甲醇溶剂加至羰基。对于镧系金属，首先观察到后一种反应。的单晶X射线衍射研究1 ·1.15Py·0.3CH 3 Ç 6 ħ 5，2