2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-1-thiomannopyranose | 1298069-73-4

• 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: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-1-thiomannopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(2-azidoethylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 1298069-73-4
• 化学式: C₁₆H₂₃N₃O₉S
• 分子量: 433.439
• InChiKey: ITHWQGBUNDENEJ-RBGFHDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-1-thiomannopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以95%的产率得到2-azidoethyl α-D-1-thiomannopyranose
  参考文献：
  名称：

  硫糖萘二亚胺偶联物：具有抗寄生虫和抗癌活性的 G-四链体配体

  摘要：

  与非癌细胞相比，糖基与药物结合是一种利用癌细胞中葡萄糖转运蛋白 (GLUT) 过度表达的策略。与O-糖苷相比，它扩展到药物与硫糖的结合，试图利用它们更高的生物稳定性。在这里，我们合成了一系列硫糖萘二亚胺偶联物作为 G-四链体配体，并探索了氨基侧链的修饰，比较了二甲基氨基和吗啉基。然后，我们研究了它们在结肠癌细胞中的抗增殖活性，以及​​它们在T. brucei和L. major中的抗寄生虫活性寄生虫，以及它们结合四链体的能力及其细胞摄取和定位。我们在哺乳动物细胞和寄生虫中观察到糖-NDI-NMe 2衍生物的毒性高于糖-NDI-morph 化合物。我们的实验表明，与四链体的结合效率较低和对 carb-NDI-morph 衍生物的细胞摄取较差可能是这些差异的原因。我们发现O -carb-NDI 和S -carb-NDI之间的细胞毒性差异很小，除了针对非癌性人类成纤维细胞 MRC-5，其中硫糖-NDI

  DOI：

  10.1016/j.ejmech.2022.114183
• 作为产物：
  描述：

  2-bromoethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以98%的产率得到2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-1-thiomannopyranose
  参考文献：
  名称：

  含糖四苯乙烯：基于聚集诱导的发射，用于研究碳水化合物与蛋白质相互作用的新型荧光探针†

  摘要：

  中性含糖四苯乙烯（TPE）被设计和制备为基于聚集诱导发射的凝集素和糖苷酶的“开启”发光传感器。通过衍生自碳水化合物与凝集素的结合，带有多价甘露糖基的TPE通过打开水溶液中水溶性四苯基乙烯基糖共轭物的荧光，显示出对Con A的良好选择性和敏感性。同时，带有纤维二糖基的TPE可用于研究基于糖苷酶诱导的聚集增强发射的酶促水解。

  DOI：

  10.1039/c0ob00680g

文献信息

• Supramolecular Diversity through Click Chemistry: Switching from Nanomicelles to 1D-Nanotubes and Tridimensional Hydrogels
  作者：Mohyeddin Assali、Juan-José Cid、Inmaculada Fernández、Noureddine Khiar

  DOI：10.1021/cm4022613

  日期：2013.11.12

  The size and shape of nanoparticles are of prominent importance for their biological activities and for their application as smart drug delivery systems. Thus, synthetic designs allowing divergent synthesis of nanoscale materials with controlled size, morphology, and surface chemistry are currently highly desirable, but they remain a major challenge. Herein, we report a simple method for the creation of supramolecular diversity from structurally related diacetylenic-based glycolipids. We have found that neoglycolipids with an amide function between the hydrophilic and hydrophobic part of the amphiphile afford tridimensional micelles, while those having a triazole self-organize into 1D-nanotubes. Additionally, at higher concentrations, the clicked amphiphiles form hydrogels through three-dimensional networks of bundled nanotubes. Photopolymerization of the obtained nanomaterials leads to the formation of conjugated polydiacetylene backbone of alternating enyne groups, which rigidify glyconanomaterial structures enhancing their physical stability. The obtained nanostructures were extensively characterized using transmission electron microscopy (TEM), scanning electron microscopy (SEM), and atomic force microscopy (AFM) techniques, enabling the confirmation of the formation of tubular structures in water for all triazolo-substituted neoglycolipids and micellar structures for the glycolipid containing an amide group. This fact refutes the so-called isosteric character of 1,2,3-triazole and amide groups, at least, at the supramolecular level and point out to the possibility of using the CuAAC between azides and alkynes to create supramolecular diversity at the nanoscale. The functionality of the gel was, moreover, evaluated as a nanocontainer for the incarceration and controlled release of the antitumoral topotecan.