N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane | 121196-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane
• 英文别名: 2-[bis[(3,5-dimethylpyrazol-1-yl)methyl]amino]ethanol
• CAS: 121196-74-5
• 化学式: C₁₄H₂₃N₅O
• 分子量: 277.37
• InChiKey: ZHGCYFVHHLQKKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper tetrafluoroborate hexahydrate 、 N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane 以 甲醇 为溶剂， 生成 {Cu(II)((N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane)H2O)}BF4
  参考文献：
  名称：

  Synthesis, characterization and catecholase activity of a series of novel mononuclear Cu(II) complexes derived from a tripodal ligand

  摘要：

  DOI：

  10.1016/s0020-1693(00)83428-3
• 作为产物：
  描述：

  3,5-二甲基吡唑 以 乙醇 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane
  参考文献：
  名称：

  Tridentate bipyrazole compounds with a side-arm as a new class of antitumor agents

  摘要：

  通过一步法合成且产率良好的八个具有不同侧臂的三齿双吡唑衍生物。利用MTT比色法测定产物对三类肿瘤细胞系的细胞毒活性——人乳腺癌细胞系MDA-MB-231、人前列腺癌细胞系PC3和人结直肠癌细胞系LoVo。结构-活性关系反映了取代药物的影响。在该系列中，有两种化合物对LoVo细胞系显示出显著的体外抗增殖活性，IC50值分别为2.6至2.7 μg ml−1。根据Lipinski规则，所有化合物都具有适合药物的特征。

  DOI：

  10.1007/s11164-012-0993-z

文献信息

• Characterization and catechole oxidase activity of a family of copper complexes coordinated by tripodal pyrazole-based ligands
  作者：R. Marion、M. Zaarour、N.A. Qachachi、N.M. Saleh、F. Justaud、D. Floner、O. Lavastre、F. Geneste

  DOI：10.1016/j.jinorgbio.2011.07.020

  日期：2011.11

  of the complexes was studied. The reaction rate depends on two factors. First, the presence of an oxygen atom in the third position of the side chain should be avoided to keep the effectiveness of the reaction. Second, the electronic and steric effects of substituents on the pyrazole ring strongly affect the catalytic activity of the complex. Thus, best results were obtained with complexes containing

  通过1-羟基吡唑与氨基醇之间的缩合反应合成了基于三脚架吡唑的配体家族。在吡唑环的取代基和侧链上都引入了多样性。通过与CuCl 2反应制备了相应的铜（II）配合物在四氢呋喃中。它们已通过EPR，UV光谱和循环伏安法进行了表征。EPR中没有半场分裂信号，这表明该复合物以单核形式存在于溶液中。研究了三脚架配体的取代基和侧链对配合物儿茶酚酶活性的影响。反应速率取决于两个因素。首先，应避免在侧链第三位置存在氧原子，以保持反应的有效性。第二，吡唑环上取代基的电子和空间效应强烈影响配合物的催化活性。因此，使用含有未取代的吡唑基配体的配合物可获得最佳结果。
• Synthesis and X-Ray Structure of [N,N-Bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane](3,5-dimethylpyrazole) copper(II) dinitrate
  作者：Mohamed El Kodadi、Fouad Malek、Rachid Touzani、Abdelkrim Ramdani、Sghir El Kadiri、Driss Eddike

  DOI：10.3390/81100780

  日期：——

  microwave irradiation (60 W) in the absence of solvent for 20 min [1]. Using this ligand L a new Cu(II) dinitrate complex has been prepared. The single-crystal X-ray structure of the title compound, [N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane] (3,5-dimethylpyrazole)copper(II) dinitrate, revels that the copper (II) ion is coordinated to two pyrazole nitrogens, one tertiary amine nitrogen

  三齿配体 N,N-双(3,5-二甲基吡唑-1-基甲基)-1-羟基-2-氨基乙烷 (L) 通过两当量的 1-羟甲基-3,5-缩合一步制备二甲基吡唑与一当量的 2-氨基乙醇。该反应在微波辐射 (60 W) 下，在没有溶剂的情况下进行 20 分钟 [1]。使用该配体 L 制备了一种新的二硝酸铜 (II) 配合物。标题化合物的单晶 X 射线结构，[N,N-双(3,5-二甲基吡唑-1-基甲基)-1-羟基-2-氨基乙烷](3,5-二甲基吡唑)铜(II) dinitrate，揭示铜 (II) 离子与两个吡唑氮、配体 L 和 3,5-二甲基吡唑的一个叔胺氮配位，并且在顶端位置由醇 O 原子配位。
• Synthesis and enzyme inhibitory activities of some new pyrazole-based heterocyclic compounds
  作者：Tariq Harit、Fouad Malek、Brahim El Bali、Ajmal Khan、Kourosh Dalvandi、Bishnu P. Marasini、Shagufta Noreen、Rizwana Malik、Sadia Khan、M. Iqbal Choudhary

  DOI：10.1007/s00044-011-9804-0

  日期：2012.10

  Three tridentate N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane (2), N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-cyclohexylamine (3) and 2-[bis(1,5-dimethyl-1H-pyrazol-3-ylmethyl)amino]ethan-1-ol (4) are synthesized and spectroscopically characterized together with 1-hydroxymethyl-3,5-dimethylpyrazole (1). These have been tested in inhibitory activities against various hyperactive enzymes like urease, beta-glucuronidase, phosphodiesterase, alpha-chymotrypsin, acetylcholinesterase and butyrylcholinesterase. Compounds 1, 2 and 3 were found to be selective inhibitors of urease. Compound 4 was found to be selective inhibitor of butyrylcholinesterase. The nature of the junction between pyrazoles cycles determined the activities of these tripods. While the tripods are inactive towards urease or glucuronidase, they turn to be selective towards butyrylcholinesterase.
• [<i>N</i>,<i>N</i>-Bis(3,5-dimethylpyrazol-1-ylmethyl)-1-hydroxy-2-aminoethane](3,5-dimethylpyrazole)copper(II) Diperchlorate
  作者：P. D. W. Boyd、A. K. Burrell、C. E. F. Rickard

  DOI：10.1107/s0108270197007932

  日期：1997.11.15

  The title compound, [CU(C5H8N2)(C14H23N5O)](ClO4)(2), consists Of a five-coordinate square-pyramidal copper(II) complex as its perchlorate salt, The copper(II) ion is coordinated in the basal plane by azole and amine N atoms of the N,N-bis[(3,5-dimethyl-1-pyrazolyl)methyl]-1-hydroxy-2-aminoethane(bpmhe) ligand and 3,5-dimethylpyrazole, and in the apical position by an alcohol O atom.