2-(N,N-bis(2-methylpyridyl)aminomethyl)-6-(N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)aminomethyl)-4-methylphenol | 170659-81-1

• 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: 2-(N,N-bis(2-methylpyridyl)aminomethyl)-6-(N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)aminomethyl)-4-methylphenol
• 英文别名: 2-bis[((2-pyridylmethyl)-aminomethyl)-6-((2-hydroxybenzyl)(2-pyridylmethyl))-aminomethyl]-4-methyphenol；2-[[bis(2-pyridinomethyl)amino]methyl]-6-[[[(2-hydroxyphenyl)methyl](2-pyridinylmethyl)amino]methyl]-4-methylphenol；2,6-bis[((2-pyridylmethyl)-aminomethyl)-6-((2-hydroxybenzyl)(2-pyridylmethyl))-aminomethyl]-4-methylphenol；2-(bis(2-pyridylmethyl)aminomethyl)-6-((2-hydroxybenzyl)(2-pyridylmethyl)aminomethyl)-4-methylphenol；2-([bis(2-pyridylmethyl)amino]methyl)-6-[([(2-hydroxyphenyl)methyl]-(2-pyridylmethyl)amino)methyl]-4-methylphenol；2-(((3-((bis(pyridin-2-ylmethyl)amino)methyl)-2-hydroxy-5-methylbenzyl)(pyridin-2-ylmethyl)amino)-methyl)phenol；H2BPBPMP；2-((Bis(pyridin-2-ylmethyl)amino)methyl)-6-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-4-methylphenol；2-[[bis(pyridin-2-ylmethyl)amino]methyl]-6-[[(2-hydroxyphenyl)methyl-(pyridin-2-ylmethyl)amino]methyl]-4-methylphenol
• CAS: 170659-81-1
• 化学式: C₃₄H₃₅N₅O₂
• 分子量: 545.684
• InChiKey: VFELWMABDRXJAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  terbium(III) nitrate hexahydrate 、 2-(N,N-bis(2-methylpyridyl)aminomethyl)-6-(N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)aminomethyl)-4-methylphenol 以 甲醇 为溶剂， 以79%的产率得到[Tb(2-bis[((2-pyridyl-methyl)amino-methyl)-6-((2-hydroxy-benzyl)-(2-pyridyl-methyl))amino-methyl]-4-methyl-phenol)(NO3)(H2O)3](NO3)2
  参考文献：
  名称：

  Efficient Phosphodiester Hydrolysis by Luminescent Terbium(III) and Europium(III) Complexes

  摘要：

  The synthesis and structures of two new isostructural mononuclear [Ln(L)(NO3)(H2O)(3)](NO3)(2) complexes, with Ln = Tb (complex 1) and Eu (complex 2), which display high activity in the hydrolysis of the substrate 2,4-bis(dinitrophenyl)phosphate, are reported. These complexes displayed catalytic behavior similar to the mononuclear gadolinium complex [Gd(L)(NO3)(H2O)(3)](NO3)(2) previously reported by us (lnorg. Chem. 2008, 47, 2919-2921); one hydrolysis reaction in two stages where the diesterase and monoesterase activities could be monitored separately, with the first stage dependent on and the second independent of the complex concentration. Through potentiometric studies, electrospray ionization mass spectrometry (ESI-MS) analysis, and determination of the kinetic behaviors of 1 and 2 in acetonitrile/water solution, the species present in solution could be identified and suggested a dinuclear species, with one hydroxo group, as the most prominent catalyst under mild conditions. The complexes show high activity (k(1)= 7 and 18 s(-1) for 1 and 2, respectively) and catalytic efficiency. Complexes 1 and 2 were found to be active toward the cleavage of plasmid DNA, and complete kinetic studies were carried out. Studies with a radical scavenger (dimethylsulfoxide) confirmed the hydrolytic action of 1 and 2 in the cleavage of DNA. Studies on the incubation of distamycin with plasmid DNA suggested that 1 and 2 are regio-specific, interacting with the minor groove of DNA. These complexes displayed luminescent properties. Complex 1 showed higher emission intensity than 2 due to a more efficient energy transfer between triplet and emission levels of terbium (T -> D-5(4)), along with nonradiative deactivation mechanisms of the excited states of europium via multiphonon decays and the ligand-to-metal charge transfer state. Lifetime measurements of the D-5(4) and D-5(0) excited levels for 1 and 2, respectively, indicated the numbers of coordinated water molecules for the complexes.

  DOI：

  10.1021/ic100549u
• 作为产物：
  描述：

  2-((bis(pyridin-2-ylmethyl)amino)methyl)-6-(hydroxymethyl)-4-methylphenol 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 2-(N,N-bis(2-methylpyridyl)aminomethyl)-6-(N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)aminomethyl)-4-methylphenol
  参考文献：
  名称：

  Synthesis, Structural, Magnetic, and Redox Properties of Asymmetric Diiron Complexes with a Single Terminally Bound Phenolate Ligand. Relevance to the Purple Acid Phosphatase Enzymes

  摘要：

  New asymmetrical ligands (H2L) have been synthesized to provide both a bridging and a terminal phenolate to a pair of iron ions in order to mimic the binding of a single terminal tyrosinate at the diiron center of the purple acid phosphatases. H(2)L1 is 2-[(bis(2-pyridylmethyl)amino)methyl]-6-[((2-pyridylmethyl)(2-phenol)amino of methyl]-4-methylphenol and H2L'1 and H(2)L2 are obtained by replacing the a-phenol group by the 5-nitro-2-phenol and the 6-methyl-2-phenol residues, respectively, A series of mixed valence diiron complexes [(FeFeL)-Fe-II-L-III(X)(2)](Y) have been obtained where (X)(2) is the dianion of m-phenylenedipropionate or (H2PO4)(2) and Y = BPh4 or PF6 (L = L1, Ba (X)(2) mpdp, Y = BPh4, db: (X)(2) = (OAC)(2), Y = BPh4, Ic: (X)(2) = (OBZ)(2), Y = BPh4, Id: (X)(2) = (H2PO4)(2), Y = PF6; L = L'1: 1'a (X)(2) = mpdp, Y = BPh4; L = L2: 2c: (X)(2) = (OBz)(2), Y = BPh4, 2d: (X)(2) = (H2PO4)(2), Y = PF6. Diferric complexes have been obtained also either by direct synthesis or by iodine oxidation of the mixed valence precursor (L = L1, 3a (X)(2) = mpdp, Y = BPh4, 3d: (X)(2) = (H2PO4)(2), Y = PF6; L = L2, 4d: (X)(2) = (H2PO4)(2). Y PF6. Complex la [(FeFeL)-Fe-II-L-III(mpdp)](BPh4) has been characterized by X-ray diffraction techniques, la crystallizes in the monoclinic space group P21/a with the following unit cell parameters: a 22.038 (9) Angstrom, b = 16.195 (8) Angstrom, c = 16.536 (7) Angstrom, beta = 97.26 (1)degrees, Z = 4, The significant differences in the Fe-O bond lengths indicate that the metal centers are ordered. The complexes have been studied by electronic spectral, resonance Raman, magnetic susceptibility, Mossbauer, NMR, and electrochemical techniques, Mossbauer and NMR spectroscopies concur to probe that the valences of the mixed valence compounds are trapped in solution as well as in the solid state at room temperature. The electronic spectrum of the mixed-valence compounds are dominated by a charge transfer transition in the 400-600 nm domain which moves to the 550-660 nm range upon oxidation to the diferric state. In addition they exhibit a weak and broad intervalence transition close to 1100 nm. Electrochemical studies show that the systems exist in the three redox states Fe-II/Fe-II/(FeFeIII)-Fe-II/(FeFeIII)-Fe-III. Moreover they show that the introduction of the terminal phenol group results in a thermodynamic destabilization of the diferrous state higher than the stabilization of the diferric state. An expanded stability domain of the mixed valence state is therefore observed which is probably due mostly to the asymmetry of the compounds, in addition a chemical destabilization of the reduced state of la, Ic, and 1'a is observed, Comparison of the carboxylate and phosphate derivatives leads to attribute it to the partial dissociation in solution of the carboxylate oxygen trans to the phenolate. The latter feature bears an intrinsic resemblance with the dissociation of iron which is observed when purple acid phosphatases are reduced by dithionite. These studies clearly show the importance of tyrosine binding on the redox properties of the PAP enzymes.This questions the relationship of such a redox specificity with a hydrolytic function and raises the possibility that the latter may be redox regulated or that another (redox based) function is actually involved, possibly in line with the ability of the enzymes to react with peroxides.

  DOI：

  10.1021/ja970345q

文献信息

• A new asymmetric N5O2-donor binucleating ligand and its first FeIIFeIII complex as a model for the redox properties of uteroferrin
  作者：Ademir Neves、Marcos Aires de Brito、Valderes Drago、Klaus Griesar、Wolfgang Haase

  DOI：10.1016/0020-1693(95)04678-3

  日期：1995.9

  A new N,O-donor binucleating ligand, 2-bis[(2-pyridylmethyl)-aminomethyl}-(2-hydroxybenzyl)(2-pyridylmethyl)}-aminomethyl]-4-meth (H2BPBPMP), and its first binuclear FeIIFeIII complex have been prepared in order to provide synthetic analogues for the coordination environment on the active site of purple acid phosphatases. The complex [FeIIFeIII(BPBPMP)(OAc)2]ClO4·CH3OH was obtained from a self-assembled

  一种新的N，O供体双核配体2-双[（（2-吡啶基甲基）-氨基甲基}-（2-羟基苄基）（2-吡啶基甲基）}-氨基甲基] -4-甲基（H2BPBPMP）已经制备了双核FeIIFeIII复合物，以便在紫色酸性磷酸酶的活性位点上为配位环境提供合成的类似物。复合物[FeIIFeIII（BPBPMP）（OAc）2] ClO4·CH3OH是由Fe（ ）2·6H2B，H2BPBPMP与乙酸钠三水合物在甲醇中的自组装反应制得的。该络合物的特征在于IR，CHN，摩尔电导率，磁化率，Mossbauer，电子吸收光谱学和电化学分析方法，并且被证明是第一个具有氧化还原特性的合成类似物（E°′= 0.38 V对NHE）。子宫铁蛋白。
• New AlIIIZnII and AlIIICuII dinuclear complexes: Phosphatase-like activity and cytotoxicity
  作者：Tiago P. Camargo、José A.F. Oliveira、Thiago G. Costa、Bruno Szpoganicz、Adailton J. Bortoluzzi、Ivana M. Marzano、Priscila P. Silva-Caldeira、Mônica Bucciarelli-Rodriguez、Elene C. Pereira-Maia、Eduardo E. Castellano、Rosely A. Peralta、Ademir Neves

  DOI：10.1016/j.jinorgbio.2021.111392

  日期：2021.6

  two AlIII(μ-OH)MII (M = Zn (1) and Cu (2)) complexes with the unsymmetrical ligand H2L2-[[(2-hydroxybenzyl)(2-pyridylmethyl)]aminomethyl]-6-bis(pyridylmethyl)aminomethyl}-4-methylphenol. The complexes were characterized through elemental analysis, X-ray crystallography, IR spectroscopy, mass spectrometry and potentiometric titration. In addition, complex 2 was characterized by electronic spectroscopy

  在此，我们报道了前两种 Al III ( μ -OH)M II (M = Zn ( 1 ) 和 Cu ( 2 )) 与不对称配体 H 2 L 2-[[(2-羟基苄基)(2-吡啶基甲基)]氨基甲基]-6-双(吡啶基甲基)氨基甲基}-4-甲基苯酚。通过元素分析、X射线晶体学、红外光谱、质谱和电位滴定对配合物进行了表征。此外，配合物2通过电子光谱进行了表征。1和2水解模型底物双(2,4-二硝基苯基)磷酸酯的动力学研究显示 Michaelis-Menten 行为，其中1比2（在 pH 7.0 时）稍微活跃（8.31% ）。使用四种细菌菌株（金黄色葡萄球菌、铜绿假单胞菌、Shigella sonnei和痢疾志贺氏菌）研究了化合物的抗菌作用，两种复合物对细菌生长的抑制效果均优于磺胺吡啶，但不如四环素。研究了复合物在慢性粒细胞白血病细胞系中的暗细胞毒性和光细胞毒性（在 UV-A 光下）。配合物1和2对
• New Gadolinium Complex with Efficient Hydrolase-like Activity: A 100-Million-Fold Rate Enhancement in Diester Hydrolysis
  作者：Maryene A. Camargo、Ademir Neves、Adailton J. Bortoluzzi、Bruno Szpoganicz、Adriano Martendal、Michael Murgu、Franciele L. Fischer、Hernán Terenzi、Patricia Cardoso Severino

  DOI：10.1021/ic702167p

  日期：2008.4.1

  structure, and hydrolase-like catalytic activity of a new mononuclear gadolinium complex [Gd(L)(NO3)(H2O)3](NO3)2 (1) are reported. A clean two-stage kinetic reaction for hydrolysis of the diester 2,4-bis(dinitrophenyl)phosphate by 1 was followed, and the rate constants were determined. A high DNA cleavage activity was also demonstrated. The active species in the hydrolytic process is proposed based

  报道了一种新型单核g配合物[Gd（L）（NO3）（H2O）3]（ ）2（1）的合成，结构和类似水解酶的催化活性。进行干净的两步动力学反应，将二酯2，4-双（二硝基苯基）磷酸酯水解为1，并确定速率常数。还证明了高的DNA切割活性。根据X射线结构，电喷雾电离质谱分析，动力学和电位平衡研究1，提出了水解过程中的活性物质。
• Synthesis, Structure, Properties, and Phosphatase-Like Activity of the First Heterodinuclear Fe^IIIMn^II Complex with the Unsymmetric Ligand H₂BPBPMP as a Model for the PAP in Sweet Potato
  作者：Peter Karsten、Ademir Neves、Adailton J. Bortoluzzi、Mauricio Lanznaster、Valderes Drago

  DOI：10.1021/ic025674k

  日期：2002.9.1

  the Fe(II)Mn(II)/Fe(III)Mn(II) and Fe(III)Mn(II)/Fe(III)Mn(III) couples, respectively, appear in the cyclic voltammogram. The dinuclear Fe(III)Mn(II) center has weakly antiferromagnetic coupling with J = -6.8 cm(-1) and g = 1.93. The (57)Fe Mössbauer spectrum exhibits a single doublet, delta = 0.48 mm s(-1) and DeltaE(Q) = 1.04 mm s(-1) for the high spin Fe(III) ion. Phosphatase-like activity at pH

  新的异双核混合价配合物[Fe（III）Mn（II）（BPBPMP）（OAc）（2）] ClO（4）（1）与不对称N（5）O（2）供体配体2-bis [（ （2-吡啶基甲基）-氨基甲基）-6-（（2-羟基苄基）（2-吡啶基甲基））-氨基甲基] -4-甲基苯酚（H（2）BPBPMP）已合成并表征。化合物1在单斜晶系空间群P2（1）/ c中结晶，并具有Fe（III）Mn（II）（μ-苯氧基）-双（μ-羧基）核。与Fc / Fc（+）对应于Fe（II）Mn（II）/ Fe（III）Mn（II）和Fe（III）Mn（II）/ Fe（ III）Mn（III）对分别出现在循环伏安图中。双核Fe（III）Mn（II）中心具有弱的反铁磁耦合，J = -6.8 cm（-1），g = 1.93。（57）FeMössbauer光谱显示出一个双峰，δ= 0.48 mm s（-1）和DeltaE（Q）= 1。高自旋Fe（III）离子为04
• New Fe^IIIZn^II Complex Containing a Single Terminal Fe−O_p_henolate Bond as a Structural and Functional Model for the Active Site of Red Kidney Bean Purple Acid Phosphatase
  作者：Mauricio Lanznaster、Ademir Neves、Adailton J. Bortoluzzi、Bruno Szpoganicz、Erineu Schwingel

  DOI：10.1021/ic025892d

  日期：2002.11.1

  The new heterodinuclear complex [Fe(III)Zn(II)(BPBPMP)(OAc)(2)]ClO(4) (1) with the unsymmetrical N(5)O(2) donor ligand 2-bis[((2-pyridylmethyl)-aminomethyl)-6-[(2-hydroxybenzyl)(2-pyridylmethyl)]-aminomethyl]-4-methylphenol (H(2)BPBPMP) has been synthesized and characterized by X-ray crystallography, which reveals that the complex cation has an Fe(III)Zn(II)(mu-phenoxo)-bis(mu-carboxylato) core. Solution

  新的异双核络合物[Fe（III）Zn（II）（BPBPMP）（OAc）（2）] ClO（4）（1）与不对称N（5）O（2）供体配体2-bis [（（2 -吡啶基甲基）-氨基甲基）-6-[（2-羟基苄基）（2-吡啶基甲基）]-氨基甲基] -4-甲基苯酚（H（2）BPBPMP）的合成和X射线晶体学表征，表明复合阳离子具有Fe（III）Zn（II）（mu-phenoxo）-双（mu-羧基）核。对1的溶液研究表明，pH引起的桥接乙酸盐发生了变化，并且在弱弱条件下形成了作为高效催化剂的活性[（OH）Fe（III）Zn（II）（OH（2））]种类。提出了磷酸二酯水解的酸性条件。