2-azido-N,N-bis((pyridin-2-yl)methyl)ethanamine | 1192597-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-azido-N,N-bis((pyridin-2-yl)methyl)ethanamine
• 英文别名: N,N-bis(2-picolyl)-2-azidoethylamine；2-azido-N,N-bis(pyridin-2-ylmethyl)ethanamine
• CAS: 1192597-09-3
• 化学式: C₁₄H₁₆N₆
• 分子量: 268.321
• InChiKey: DVNGETQKYYSNNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-N,N-bis((pyridin-2-yl)methyl)ethanamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以95%的产率得到N,N-二(2-吡啶甲基)乙二胺
  参考文献：
  名称：

  Near-infrared fluorescent probe for sensitive detection of Pb(II) ions in living cells

  摘要：

  A new near-infrared fluorescent probe (NIR-PbP) for sensitive detection of Pb(II) ions in solution and living cells has been rationally designed and synthesized. The NIR-PbP is inherently non-fluorescent and gains fluorescence in the presence Pb( II) ions. The ion detection is based on Pb(II)- induced unmasking the fluorophore through the opening of the spyrocycle, with more than 500-fold fluorescence enhancement for sub-micromolar Pb(II) concentration. The NIR-PbP has high sensitivity, good photo-stability, low detection limit, and reversible response to Pb( II) ions. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2017.06.044
• 作为产物：
  描述：

  2-(双-(2-吡啶甲基)-氨基)-乙醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 叠氮磷酸二苯酯 作用下， 以 四氢呋喃 为溶剂， 反应 72.08h， 以36%的产率得到2-azido-N,N-bis((pyridin-2-yl)methyl)ethanamine
  参考文献：
  名称：

  Preparation, 99mTc-labeling and biodistribution studies of a PNA oligomer containing a new ligand derivative of 2,2′-dipicolylamine

  摘要：

  Anew azido derivative of 2,2 '-dipicolylamine (Dpa), 2-azido-N,N-bis((pyridin-2-yl)methyl)ethanamine, (Dpa-N-3) was readily prepared from the known 2-(bis(pyridin-2-ylmethyl)amino)ethanol (Dpa-OH). It was demonstrated that Dpa-N-3 could be efficiently labeled with both [Re(CO)(3)(H2O)(3)]Br and [Tc-99m(H2O)(3)(CO)(3)] to give [Re(CO)(3)(Dpa-N-3)]Br and [Tc-99m(CO)(3)(Dpa-N-3)](+), respectively. Furthermore, Dpa-N3 was successfully coupled, on the solid phase, to a Peptide Nucleic Acid (PNA) oligomer (H-4-pentynoic acid-spacer-spacer-tgca-tgca-tgca-Lys-NH2; spacer = -NH-(CH2)(2)-O-(CH2)(2)-O-CH2-CO-) using the Cu(I)-catalyzed [2 + 3] azide/alkyne cycloaddition (Cu-AAC, often referred to as the prototypical "click" reaction) to give the Dpa-PNA oligomer. Subsequent labeling of Dpa-PNA with [Tc-99m(H2O)(3)(CO)(3)](+) afforded [Tc-99m(CO)(3)(Dpa-PNA)] in radiochemical yields > 90%. Partitioning experiments in a 1-octanol/water system were carried out to get more insight on the lipophilicity of [Tc-99m(CO)(3)(Dpa-N-3)(+) and [Tc-99m(CO)(3)(Dpa-PNA)]. Both compounds were found rather hydrophilic (log D-o/w values at pH = 7.4 are -0.50: [Tc-99m(CO)(3)(Dpa-N-3)](+) and 0.85: [Tc-99m(CO)(3)(Dpa-PNA)]. Biodistribution studies of [Tc-99m(CO)(3)(Dpa-PNA)] in Wistar rats showed a very fast blood clearance (0.26 +/- 0.1 SUV, 1 h p.i.) and modest accumulation in the kidneys (5.45 +/- 0.45 SUV, 1 h p.i.). There was no significant activity in the thyroid and the stomach, demonstrating a high in vivo stability of the Tc-99m-labeled Dpa-PNA conjugate. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.06.011

文献信息

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  作者：Gui-Chao Kuang、Heather A. Michaels、J. Tyler Simmons、Ronald J. Clark、Lei Zhu

  DOI：10.1021/jo101305m

  日期：2010.10.1

  complex of T6 were characterized by X-ray crystallography. The structure of [Cu(T1)2(H2O)2](ClO4)2 reveals the interesting synergistic effect of hydrogen bonding, π−π stacking interactions, and metal coordination in forming a one-dimensional supramolecular construct in the solid state. The tetradentate coordination mode of T6 may be incorporated into designs of new molecule sensors and organometallic

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• Synthesis of Side-Chain Modified Peptides Using Iterative Solid Phase ‘Click' Methodology
  作者：Xuejian Liu、Robert B. P. Elmes、Katrina A. Jolliffe

  DOI：10.1071/ch16567

  日期：——

  modified peptides have been prepared via an iterative sequence of peptide couplings and azide–alkyne cycloadditions (‘click’ reactions) using Fmoc-solid phase peptide synthesis. This efficient modular synthetic route allows the systematic and sequential incorporation of a variety of side-chain modifications onto short peptides. The versatility of this approach was demonstrated by the synthesis of a series

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• Histidine Analog Amino Acids Providing Metal-Binding Sites Derived from Bioinorganic Model Systems
  作者：André Nadler、Christina Hain、Ulf Diederichsen

  DOI：10.1002/ejoc.200900472

  日期：2009.9

  Metalloproteins are of utmost importance for nearly all biological processes. Valuable information about their functionalities came from mutagenesis studies and led to the de novo design of artificial proteins. Advances in peptide chemistry enable the total synthesis of complete proteins and allow the incorporation of non-proteinogenic amino acids. Chelating amino acids utilized to introduce artificial

  金属蛋白对于几乎所有的生物过程都至关重要。关于其功能的宝贵信息来自诱变研究，并导致了人工蛋白质的从头设计。肽化学的进步使完整蛋白质的全合成成为可能，并允许掺入非蛋白氨基酸。用于将人工金属结合位点引入蛋白质的螯合氨基酸应模拟天然残基的侧链，以尽量减少目标蛋白质内的结构后果。在本文中，描述了一种合成方法，用于制备带有通过三唑形成连接到 β-碳的金属配体系统的氨基酸。因此，产生了一个组氨酸异构体，在肽骨架附近有一个额外的金属结合位点。
• A luminogenic lanthanide-based probe for the highly selective detection of nanomolar sulfide levels in aqueous samples
  作者：Margaret L. Aulsebrook、Suvendu Biswas、Franklin M. Leaver、Michael R. Grace、Bim Graham、Amy M. Barrios、Kellie L. Tuck

  DOI：10.1039/c7cc01764b

  日期：——

  bimetallic terbium(III)/copper(II) complex (Tb-1·Cu2+) for the time-gated luminescent detection of hydrogen sulfide in aqueous samples is reported. The probe shows excellent selectivity towards HS− over various anions and cations, including the ions common to natural waterways and waste water samples, displaying a 73-fold increase in luminescence in the presence of sulfide. The probe exhibits extremely

  报道了一种双金属ter（Ⅲ）/铜（Ⅱ）配合物（Tb-1·Cu 2+）用于水样中硫化氢的时间门控发光检测。探针显示朝向HS优异的选择性-在不同的阴离子和阳离子，其中包括离子共同天然水道和废水样品，显示在硫化物的存在下，在发光的73倍的增加。该探针具有极快的反应时间和较低的检测限（130 nM）。该探针用于定量工业“酸水”样品中的硫化物，其结果与两种独立测定方法（亚甲基蓝和AzMC）的硫化物非常吻合。
• NOUVEAUX AZOTURES, PROCÉDÉS DE FABRICATION ET LEURS APPLICATIONS
  申请人：Commissariat à l'Énergie Atomique et aux Énergies Alternatives

  公开号：EP2903973B1

  公开（公告）日：2017-06-28