2,6-bis(4-methyl piperazin-1-yl-methyl)-4-formyl phenol | 1141497-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis(4-methyl piperazin-1-yl-methyl)-4-formyl phenol
• 英文别名: 2,6-bis[(N-methylpiperazine-1-yl)methyl]-4-formylphenol；2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formlyphenol；2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formylphenol；4-Hydroxy-3,5-bis[(4-methylpiperazin-1-yl)methyl]benzaldehyde；4-hydroxy-3,5-bis[(4-methylpiperazin-1-yl)methyl]benzaldehyde
• CAS: 1141497-65-5
• 化学式: C₁₉H₃₀N₄O₂
• 分子量: 346.473
• InChiKey: SPSNBIRTXULLBL-UHFFFAOYSA-N

物化性质

• 沸点：
  482.9±45.0 °C(predicted)
• 密度：
  1.176±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-methyl piperazin-1-yl-methyl)-4-formyl phenol 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 16.0h， 生成 (E)-2,6-bis((4-methylpiperazin-1-yl)methyl)-4-styrylphenol
  参考文献：
  名称：

  10.14233/ajchem.2024.31942

  摘要：

  A series of 12 stilbene derivatives (23-34) were synthesized by reacting benzyl-triphenylphosphonium chlorides (9-14) and hydrochloride salt of 3,5-disubstituted-4-hydroxybenzaldehydes (21-22). The synthesized molecules were tested against the human breast cancer cell line MCF7 by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in 10% Dulbecco’s modified Eagle Medium (DMEM). Compound 23 exhibited significant cytotoxicity, with 1.11% viability at a concentration of 200 µM, compared to the reference standard resveratrol (15.14%) and 5-fluorouracil (51.86%). All the synthesized derivatives demonstrated equipotency to 5-fluorouracil (5-FU) at all the tested concentrations. The docking study was conducted on the tyrosine-protein kinase/Janus Kinase 2(JAK2) receptor using Autodock Vina. The results of the docking study suggest that, with the exception of compounds 29 (-6.7 kcal/mol) and 32 (-7.1 kcal/mol), most of the synthesized derivatives have exhibited glide scores greater than the standard resveratrol (-7.8 kcal/mol). This implies that these compounds 23-34 have a strong binding affinity to the JAK2 receptor, which is relevant in the context of cancer research, as JAK2 is associated with various signaling pathways involved in cell proliferation and survival.

  DOI：

  10.14233/ajchem.2024.31942
• 作为产物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 对羟基苯甲醛 以 甲醇 为溶剂， 反应 25.0h， 以8.1 g的产率得到2,6-bis(4-methyl piperazin-1-yl-methyl)-4-formyl phenol
  参考文献：
  名称：

  推挽式卟啉及其金属配合物的光谱、氧化还原和生物学研究

  摘要：

  我们合成了一系列在中间位置上含有供体和受体取代基的推挽式卟啉，并检查了它们的光谱和生物学特性。推挽式卟啉在中间位置含有强供体 NH2 和受体 NO2，其中供体基团与配体 (2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formlyphenol (L ) 与卟啉形成亚胺键。席夫碱配体 5-[4(2,6-bis(4-methylpiperazine-1-yl-methyl)-4-iminomethylphenol)phenyl]-10,15,20-tris(4 -nitrophenyl) porphyrin [an3(TPP)L] 可以由 2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formylphenol (L) 和 5-(4-aminophenyl)-10, 15 合成,20-三(4-硝基苯基)卟啉。推挽式卟啉[

  DOI：

  10.5012/bkcs.2010.31.9.2656

文献信息

• Synthesis, characterization and bioactive evaluation of copper(II) 5,10,15,20-tetrakis[α,α,α,α-2-(2,6-bis(4-methylpiperazine-1-yl-methyl)-4-iminomethyl phenol)phenyl] porphyrin: A picket-fence porphyrin
  作者：K. Rajesh、A. Kalilur Rahiman、K. Shanmuga Bharathi、S. Sreedaran、V. Gangadevi、V. Narayanan

  DOI：10.1016/j.saa.2010.07.005

  日期：2010.10

  positions of tetrakis(o-aminophenyl)porphyrin. The synthesis of picket-fence porphyrin is initiated by the preparation of the tetrakis(o-nitrophenyl)porphyrin followed by the nitro to amino reduction and subsequent condensation with Schiff base ligand to form imine linkages of porphyrin complexes. The synthesis and characterization of a new series of picket-fence porphyrins and their copper complexes are

  我们有兴趣通过在四（邻氨基苯基）卟啉的邻苯基位置添加更多的大体积取代基来构建更深的小腔。通过制备四（邻-硝基苯基）卟啉，然后将硝基还原成氨基，然后与席夫碱配体缩合以形成卟啉配合物的亚胺键，开始了栅栏卟啉的合成。描述了一系列新的栅栏卟啉及其铜配合物的合成和表征。可以合成5,10,15,20-四[[α，α，α，α-2-（2,6-双（4-甲基哌嗪-1-基甲基）-4-亚氨基甲基苯酚）苯基]卟啉由2,6-双[4-甲基哌嗪-1-基-甲基] -4-甲酰基苯酚（L）和5,10,15,20-四[α，α，α，α-邻-硝基苯基]-卟啉组成。5,10,15,20-Tetra [α，α，α，通过还原5,10,15,20-四[α，α，α，α，o-硝基酚1]-卟啉获得α-o-氨基苯基1]-卟啉。对所有栅栏卟啉配合物的光谱，电化学，抗菌，抗真菌和细胞毒性特性进行了表征和研究。
• Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes
  作者：K. Rajesh、A. Kalilur Rahiman、K. Shanmuga Bharathi、S. Sreedaran、V. Gangadevi、V. Narayanan

  DOI：10.5012/bkcs.2010.31.9.2656

  日期：2010.9.20

  20-tris(4-nitrophenyl) porphyrin [an3(TPP)L] can be synthesized from 2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formylphenol (L) and 5-(4-aminophenyl)-10, 15,20-tris(4-nitrophenyl)porphyrin. The push-pull porphyrin [an3(TPP)L] was metallated to get copper, nickel and zinc complexes. The spectral, electrochemical, antibacterial, antifungal and cytotoxicity properties of all the donor- acceptor push-pull porphyrins and

  我们合成了一系列在中间位置上含有供体和受体取代基的推挽式卟啉，并检查了它们的光谱和生物学特性。推挽式卟啉在中间位置含有强供体 NH2 和受体 NO2，其中供体基团与配体 (2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formlyphenol (L ) 与卟啉形成亚胺键。席夫碱配体 5-[4(2,6-bis(4-methylpiperazine-1-yl-methyl)-4-iminomethylphenol)phenyl]-10,15,20-tris(4 -nitrophenyl) porphyrin [an3(TPP)L] 可以由 2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formylphenol (L) 和 5-(4-aminophenyl)-10, 15 合成,20-三(4-硝基苯基)卟啉。推挽式卟啉[
• Synthesis of new ‘end-off’ μ-phenoxo and bis-μ-acetato tri-bridged copper(II), nickel(II) and zinc(II) complexes: Spectral, magnetic, electrochemical and catalytic studies
  作者：K. Shanmuga Bharathi、A. Kalilur Rahiman、K. Rajesh、S. Sreedaran、P.G. Aravindan、D. Velmurugan、V. Narayanan

  DOI：10.1016/j.poly.2006.04.022

  日期：2006.11

  A new end-off type acyclic ligand with two N-methyl piperazine arms, 2,6-bis[(4-methyl piperazin-1-yl)]-4-formyl phenol [L], has been synthesized by a simple Mannich reaction. The mono and binuclear complexes of Cu(II), Ni(II) and Zn(II) have been prepared. The complexes were characterized by elemental and spectral analysis. The EPR spectrum of the mononuclear copper complex shows four hyperfine splittings and the binuclear complex shows a broad signal due to an anti-ferromagnetic interaction. The room temperature magnetic moment of the mono and binuclear copper complexes are found to be 1.72 mu(B) (mu(eff)) and 1.58 mu(B) (mu(eff)), respectively. The mononuclear Ni(II) complex is square planar and diamagnetic, whereas the six-coordinated binuclear Ni(II) complex shows a magnetic moment value of 2.98 mu(B) (mu(eff)). Cyclic voltammetric studies evidenced one irreversible reduction wave for all the mononuclear complexes and two irreversible one-electron reduction waves for the binuclear complexes are obtained in the cathodic region. In the anodic region, one irreversible oxidation wave for the mononuclear nickel(II) complex and two irreversible oxidation waves for the binuclear nickel(II) complexes are obtained. Kinetic studies on the oxidation of pyrocatechol to o-quinone using the mono and binuclear copper(II) complexes as catalysts and on the hydrolysis of 4-nitrophenylphosphate using the mono and binuclear copper(II), nickel(II) and zinc(II) complexes as catalysts were carried out. The binuclear complexes have higher rate constant values than those of the corresponding mononuclear complexes. The rate constant values for the complexes for the hydrolysis are in the order nickel(II) > copper(II) > zinc(II). (C) 2006 Elsevier Ltd. All rights reserved.
• 10.14233/ajchem.2024.31942
  作者：Pirgal, Dimple、Karki, Subhas S.、Kumar, Sujeet、Metikurki, Basavraj

  DOI：10.14233/ajchem.2024.31942

  日期：——

  A series of 12 stilbene derivatives (23-34) were synthesized by reacting benzyl-triphenylphosphonium chlorides (9-14) and hydrochloride salt of 3,5-disubstituted-4-hydroxybenzaldehydes (21-22). The synthesized molecules were tested against the human breast cancer cell line MCF7 by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in 10% Dulbecco’s modified Eagle Medium (DMEM). Compound 23 exhibited significant cytotoxicity, with 1.11% viability at a concentration of 200 µM, compared to the reference standard resveratrol (15.14%) and 5-fluorouracil (51.86%). All the synthesized derivatives demonstrated equipotency to 5-fluorouracil (5-FU) at all the tested concentrations. The docking study was conducted on the tyrosine-protein kinase/Janus Kinase 2(JAK2) receptor using Autodock Vina. The results of the docking study suggest that, with the exception of compounds 29 (-6.7 kcal/mol) and 32 (-7.1 kcal/mol), most of the synthesized derivatives have exhibited glide scores greater than the standard resveratrol (-7.8 kcal/mol). This implies that these compounds 23-34 have a strong binding affinity to the JAK2 receptor, which is relevant in the context of cancer research, as JAK2 is associated with various signaling pathways involved in cell proliferation and survival.
• Comparison of mononuclear and dinuclear copper(<scp>ii</scp>) biomimetic complexes: spectroelectrochemical mechanistic study of their catalytic pathways
  作者：Milan Sýs、Jana Kocábová、Jitka Klikarová、Miroslav Novák、Robert Jirásko、Michaela Obluková、Tomáš Mikysek、Romana Sokolová

  DOI：10.1039/d2dt01610a

  日期：——

  values of KM = 272.93 (223.02; 1616) μmol L−1 and Vmax of 0.981 (1.617; 1.689) μmol L−1 s−1. The role of water content in the solvent is also discussed. The dinuclear complexes C1 and C2 were found to be more efficient catalysts than mononuclear complex C3. The mode of catalytic action was characterized via cyclic voltammetry, spectrophotometry, and UV-Vis spectroelectrochemistry. The catalytic mechanism

  两种类儿茶酚酶仿生催化剂，即两种双核铜配合物[Cu 2 (L1)(OH)(H 2 O)(EtOH)][ClO 4 ] 2 ( C1 )和[Cu 2 Ac 2 O(L1)ClO 4 ] ( C2 ) 与 2,6-双(4-甲基哌嗪-1-基-甲基)-4-甲酰基-苯氧基配体 (L1) 以及单核络合物 Cu(ClO 4 ) 2 (L2) ( C3 ) ) 含配体 1,2-(C 5 H 4 N-6-OCH 3 -2-CH N) 2 CH 2 CH 2(L2), 被合成。研究和比较了它们的催化途径。使用 Michaelis-Menten 模型评估化合物C1 (和C2、C3 ) 的催化活性由K M = 272.93 (223.02; 1616) μmol L -1和V max的值表示为 0.981 (1.617; 1.689) μmol L -1秒-1。还讨论了溶剂中水含量的作用。发现双核配合物C1和C2