N,N-bis[2-(tert-butoxycarbonylamino)ethyl]propargylamine | 1179524-91-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-bis[2-(tert-butoxycarbonylamino)ethyl]propargylamine
• 英文别名: 3-bis[2-(tert-butoxycarbonylamino)ethyl]propargylamine；N,N-bis[2-(tert-butoxycarbonylamino)-ethyl]propargylamine；tert-butyl N-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl-prop-2-ynylamino]ethyl]carbamate
• CAS: 1179524-91-4
• 化学式: C₁₇H₃₁N₃O₄
• 分子量: 341.451
• InChiKey: GEYFIFQWXXNINI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis[2-(tert-butoxycarbonylamino)ethyl]propargylamine 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 36.0h， 生成 methyl 6-deoxy-6-(4-(2,2-diaminoethylaminomethyl)-1H-1,2,3-triazol-1-yl)-2,3,4-tri-O-hexanoyl-α-D-glucopyranoside dihydrochloride
  参考文献：
  名称：

  Trehalose- and Glucose-Derived Glycoamphiphiles: Small-Molecule and Nanoparticle Toll-Like Receptor 4 (TLR4) Modulators

  摘要：

  An increasing number of pathologies have been linked to Toll-like receptor 4 (TLR4) activation and signaling, therefore new hit and lead compounds targeting this receptor activation process are urgently needed. We report on the synthesis and biological properties of glycolipids based on glucose and trehalose scaffolds which potently inhibit TLR4 activation and signaling in vitro and in vivo. Structure-activity relationship studies on these compounds indicate that the presence of fatty ester chains in the molecule is a primary prerequisite for biological activity and point to facial amphiphilicity as a preferred architecture for TLR4 antagonism. The cationic glycolipids here presented can be considered as new lead compounds for the development of drugs targeting TLR4 activation and signaling in infectious, inflammatory, and autoimmune diseases. Interestingly, the biological activity of the best drug candidate was retained after adsorption at the surface of colloidal gold nanoparticles, broadening the options for clinical development.

  DOI：

  10.1021/jm501182w
• 作为产物：
  描述：

  3-溴丙炔 、 二(2-甲基-2-丙基)(亚氨基二-2,1-乙二基)二氨基甲酸酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以58%的产率得到N,N-bis[2-(tert-butoxycarbonylamino)ethyl]propargylamine
  参考文献：
  名称：

  Preorganized macromolecular gene delivery systems: amphiphilic β-cyclodextrin “click clusters”

  摘要：

  基于β-环糊精支架的基因传递系统通过结合铜(I)催化的叠氮-炔烃耦合（“点击化学”）和次级羟基的高效酰化方法合成而成；分子柔性、电荷密度和疏水-亲水平衡是可以通过点击方法精细调整的关键参数。

  DOI：

  10.1039/b903635k

文献信息

• Tuning the Topological Landscape of DNA–Cyclodextrin Nanocomplexes by Molecular Design
  作者：Tania Neva、Ana I. Carbajo‐Gordillo、Juan M. Benito、Hugo Lana、Gema Marcelo、Carmen Ortiz Mellet、Conchita Tros de Ilarduya、Francisco Mendicuti、José M. García Fernández

  DOI：10.1002/chem.202002951

  日期：2020.11.26

  Original molecular vectors that ensure broad flexibility to tune the shape and surface properties of plasmid DNA (pDNA) condensates are reported herein. The prototypic design involves a cyclodextrin (CD) platform bearing a polycationic cluster at the primary face and a doubly linked aromatic module bridging two consecutive monosaccharide units at the secondary face that behaves as a topology‐encoding

  本文报道了确保广泛的灵活性以调节质粒DNA（pDNA）缩合物的形状和表面特性的原始分子载体。原型设计涉及一个在主面上带有聚阳离子簇的环糊精（CD）平台，以及在副面上桥接两个连续单糖单元的双链芳族模块，该单元充当拓扑结构编码元素。在分子水平上的细微差异随后转化为纳米级的不同形态，包括杆，蠕虫，超环面，小球，椭球和椭球。对转染能力的体外评估显示出明显的选择性差异作为纳米复合物形态的函数。明显高的转染效率与椭圆形或球形以及pDNA链和CD双层的层状内部排列有关。计算研究支持这种超分子大厦的稳定性与DNA模板化后分子载体形成非共价二聚体的趋势直接相关。因为二聚体的稳定性取决于聚阳离子簇的质子化状态，所以共聚集体显示出pH响应性，这有助于内体逃逸并及时释放DNA，这是成功转染的关键步骤。结果为构建完全适用于优化方案的完全合成且完美单分散的非病毒基因递送系统提供了一种通用策略。计算研究支持这种超分子大
• Synthesis of new <i>p-tert</i>-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates
  作者：Vladimir A Burilov、Guzaliya A Fatikhova、Mariya N Dokuchaeva、Ramil I Nugmanov、Diana A Mironova、Pavel V Dorovatovskii、Victor N Khrustalev、Svetlana E Solovieva、Igor S Antipin

  DOI：10.3762/bjoc.14.173

  日期：——

  The synthesis of new calix[4]arenes adopting a cone stereoisomeric form bearing two or four azide fragments on the upper rim and water-soluble triazolyl amphiphilic receptors with two or four polyammonium headgroups via copper-catalyzed azide-alkyne cycloaddition reaction has been performed for the first time. It was found that the synthesized macrocycles form stable aggregates with hydrodynamic diameters

  已经通过铜催化的叠氮化物-炔烃环加成反应合成了新的杯芳烃[4]芳烃，其采用在上边缘带有两个或四个叠氮化物片段和具有两个或四个聚铵头基的水溶性三唑基两亲受体的圆锥立体异构形式，用于第一次。发现合成的大环化合物在水溶液中形成了稳定的聚集体，其流体动力学直径在150-200 nm之间，电动势约为+40至+60 mV。使用a和曙红Y作为染料探针，使用胶束方法测量了临界聚集浓度（CAC）值。四烷基取代的大环化合物12a，b的CAC值（均为5 µM）明显低于二烷基取代的大环化合物10a，b的CAC值（分别为790和160 µM）。大环化合物10a，b和12a的前胶束聚集体，b与染料曙红Y一起用于通过染料置换程序进行核苷酸感测。不常见的是，二取代的大环化合物10a，b比腺苷5'-三磷酸酯（ATP）更有效地结合电荷较少的腺苷5'-二磷酸酯（ADP）。阐述了一种简单的比色法，该方法基于用10b装饰的聚二乙炔囊泡进行ADP的肉眼检测，检测限为0
• Dynamic Self-Assembly of Polycationic Clusters Based on Cyclodextrins for pH-Sensitive DNA Nanocondensation and Delivery by Component Design
  作者：Laura Gallego-Yerga、M. José González-Álvarez、Natalia Mayordomo、Francisco Santoyo-González、Juan M. Benito、Carmen Ortiz Mellet、Francisco Mendicuti、José M. García Fernández

  DOI：10.1002/chem.201402026

  日期：2014.5.26

  The ability of cyclodextrin‐based polycationic cluster to undergo reversible DNA condensation and release in a physiologically useful pH window has been finely tuned by the installation of a capping xylylene moiety at the secondary face of the cyclooligosaccharide. This strategy can be exploited advantageously in the design of self‐assembling nonviral gene‐delivery systems from molecular entities.

  通过在环寡糖的第二面上安装一个封端的亚二甲苯基，可以很好地调节基于环糊精的聚阳离子簇在可逆的pH窗口中发生可逆的DNA缩合和释放的能力。从分子实体设计自组装非病毒基因递送系统时，可以有利地利用该策略。
• Symmetry Complementarity-Guided Design of Anthrax Toxin Inhibitors Based on β-Cyclodextrin: Synthesis and Relative Activities of Face-Selective Functionalized Polycationic Clusters
  作者：Alejandro Díaz-Moscoso、Alejandro Méndez-Ardoy、Fernando Ortega-Caballero、Juan M. Benito、Carmen Ortiz Mellet、Jacques Defaye、Tanisha M. Robinson、Adiamseged Yohannes、Vladimir A. Karginov、José M. García Fernández

  DOI：10.1002/cmdc.201000419

  日期：2011.1.3

  potential anthrax toxin inhibitors based on the β‐cyclodextrin (βCD) scaffold were developed by exploiting face‐selective CuI‐catalyzed azide–alkyne 1,3‐cycloadditions, amine–isothiocyanate coupling, and allyl group hydroboration–oxidation/hydroxy → amine replacement reactions. The molecular design follows the “symmetry–complementarity” concept between homogeneously functionalized polycationic βCD derivatives

  通过利用面选择性Cu I催化的叠氮化物-炔烃1,3-环加成反应，胺-异硫氰酸酯偶联以及烯丙基氢硼化-氧化/开发了三种基于β-环糊精（βCD）支架的潜在炭疽毒素抑制剂新系列。羟基→胺替代反应。分子设计遵循均相官能化的聚阳离子βCD衍生物与保护性抗原（PA）之间的“对称性-互补性”概念，PA是已知形成C 7的炭疽毒素的一种成分致死和浮肿因子利用细胞膜上的对称孔获得细胞溶质的通道。本文报道了一系列阳离子分子的数量，排列和表面位置不同的βCD衍生物的合成和抗毒素活性。这些结果为新候选人对抗炭疽威胁的结构-活动关系发展计划奠定了基础。
• Synthesis of Water-Soluble Polyammonium Thiacalix[4]arene Derivative and Its Interaction with Calf Thymus DNA
  作者：V. A. Burilov、D. A. Mironova、I. A. Grygoriev、A. M. Valiyakhmetova、S. E. Solovieva、I. S. Antipin

  DOI：10.1134/s1070363220010156

  日期：2020.1

  A water-soluble thiacalix[4]arene derivative containing four diethylenetriamine fragments in 1,3-alternate stereoisomeric form has been obtained for the first time. Using ethidium bromide, it has been found that the macrocycle can interact with calf thymus DNA. The macrocycle has been found to interact with DNA via groove binding. The presence of four diethylenetriamine fragments on the calixarene

  首次获得了含有四个1,3-交替立体异构形式的二亚乙基三胺片段的水溶性噻唑杯[4]芳烃衍生物。使用溴化乙锭发现，大环可以与小牛胸腺DNA相互作用。已经发现大环通过凹槽结合与DNA相互作用。杯芳烃平台上四个二亚乙基三胺片段的存在导致与DNA的多价相互作用，与单个二亚乙基三胺相比，结合常数增加了两个数量级。