5,11,17,23-tetra(n-hexyl)-25,26,27,28-tetrakis(3-aminopropoxy)calix[4]arene | 1058142-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetra(n-hexyl)-25,26,27,28-tetrakis(3-aminopropoxy)calix[4]arene
• 英文别名: 3-[[26,27,28-Tris(3-aminopropoxy)-5,11,17,23-tetrahexyl-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propan-1-amine
• CAS: 1058142-29-2
• 化学式: C₆₄H₁₀₀N₄O₄
• 分子量: 989.522
• InChiKey: ZBIGSKSEEJXACM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  72
• 可旋转键数：
  36
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra(n-hexyl)-25,26,27,28-tetrakis(3-aminopropoxy)calix[4]arene 、 1,3-二-BOC-2-(三氟甲基磺酰)胍 以 二氯甲烷 为溶剂， 生成 5,11,17,23-tetra(n-hexyl)-25,26,27,28-tetrakis[3-(bis-Boc-guanidine)propoxy]calix[4]arene
  参考文献：
  名称：

  Lower Rim Guanidinocalix[4]arenes: Macrocyclic Nonviral Vectors for Cell Transfection

  摘要：

  Guanidinium groups were introduced through a spacer at the lower rim of calix[4]arenes in the cone conformation to give new potential nonviral vectors for gene delivery. Several structural modifications were explored, such as the presence or absence of a macrocyclic scaffold, lipophilicity of the backbone, length of the spacer, and nature of the charged groups, in order to better understand the factors which affect the DNA condensation ability and transfection efficiency of these derivatives. The most interesting compound was a calix[4]arene unsubstituted at the upper rim and having four guanidinium groups linked at the lower rim through a three carbon atom spacer. This compound, when formulated with DOPE, showed low toxicity and transfection efficiency higher than the commercially available lipofectamine LTX in the treatment of human Rhabdomiosarcoma and Vero cells. Most of the investigated compounds showed a tendency to self-aggregate in pure water or in the presence of salts, as evidenced by NMR and AFM studies, and it was found that the ability to condense DNA plasmids in nanometric globules is a necessary but not sufficient condition for transfection. The superiority of macrocyclic vectors over linear Gemini-type analogues and of guanidinium compared to other ammonium head groups in determining the biological activity of the vectors was also ascertained.

  DOI：

  10.1021/bc2006829
• 作为产物：
  描述：

  5,11,17,23-tetra-(n-hexyl)-25,26,27,28-tetrakis(3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy)calix[4]arene 在 一水合肼 作用下， 以 乙醇 为溶剂， 以65%的产率得到5,11,17,23-tetra(n-hexyl)-25,26,27,28-tetrakis(3-aminopropoxy)calix[4]arene
  参考文献：
  名称：

  Macrocyclic Nonviral Vectors: High Cell Transfection Efficiency and Low Toxicity in a Lower Rim Guanidinium Calix[4]arene

  摘要：

  New multivalent cationic lipids, one of them showing high efficiency and low toxicity in cell transfection, have been obtained by attaching guanidinium groups at the lower rim of calix[4]arenes.

  DOI：

  10.1021/ol801326d

文献信息

• CO₂ Capture by Multivalent Amino-Functionalized Calix[4]arenes: Self-Assembly, Absorption, and QCM Detection Studies
  作者：Laura Baldini、Monica Melegari、Valentina Bagnacani、Alessandro Casnati、Enrico Dalcanale、Francesco Sansone、Rocco Ungaro

  DOI：10.1021/jo200650f

  日期：2011.5.20

  The reactivity of CO2 with polyamino substrates based on calix[4]arenes and on a difunctional, noncyclic model has been studied. All the compounds react with CO2 in chloroform to form ammonium carb innate salts. However, the number, topology, and conformational features of the amino-functionalized arms present on the multivalent scaffold have a remarkable influence on the reaction efficiency and on the product composition. Tetraaminocalix[4]arenes 1-3 rapidly and efficiently react with 2 equiv of CO2, yielding highly stable hydrogen-bonded dimers formed by the self-assembly of two bis-ammonium bis-carbamate intramolecular salts. 1,3-Diaminocalix[4]arene 4 absorbs 1 mol of CO2, affording less stable zwitterionic ammonium carbamates. Gemini compound 5 reacts with CO2 in a 1:1 stoichiometry, forming hydrogen. bonded dimers of ammonium carbamate derivatives of moderate stability. For upper rim 1,3-diaminocalix[4]arene 6, in addition to the labile intramolecular salt, the presence of a self-assembled polymer was also detected. These systems were fully characterized in solution by H-1 and C-13 NMR spectroscopy, whereas the corresponding gas-solid reactions were further investigated by QCM measurements. Interestingly, the high affinity and reversibility of CO2 uptake shown by 1,3-diamino calix[4]arene 4 enabled us to attain a promising QCM device for carbon dioxide sensing.