25,26,27,28-tetrakis(propoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene | 219712-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,26,27,28-tetrakis(propoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene
• 英文别名: 5,11,17,23-tetracyano-25,26,27,28-tetrapropoxycalix[4]arene；25,26,27,28-Tetrapropoxypentacyclo[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-dodecaene-5,11,17,23-tetracarbonitrile
• CAS: 219712-20-6；950744-66-8
• 化学式: C₄₄H₄₄N₄O₄
• 分子量: 692.858
• InChiKey: SQPHVZWBJDIAEL-UHFFFAOYSA-N

物化性质

• 沸点：
  884.0±65.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25,26,27,28-tetrakis(propoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene 在 氢氧化钾 、 二甲氨基三氟化硫 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 25,26,27,28-Tetrapropoxypentacyclo[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-dodecaene-5,11,17,23-tetracarbonyl fluoride
  参考文献：
  名称：

  Heterodimerization Studies of Calix[4]arene Derivatives in Polar Solvents

  摘要：

  Several calix[4]arene derivatives propylated on the lower rim and substituted on the upper rim with amino or carboxyl groups have been synthesized. Examples include calixarenes substituted with alanino (C- and N-linked), amino, carboxy, carboxyphenyl, and amidino groups. The self-assembly of these derivatized calixarenes into heterodimers has been studied by NMR in DMSO-d(6) or CD3OD with 5% aqueous phosphate buffer.

  DOI：

  10.1021/ol060612+
• 作为产物：
  描述：

  25,26,27,28-tetrapropyloxycalix[4]arene 在 N-甲基吡咯烷酮 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.25h， 生成 25,26,27,28-tetrakis(propoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene
  参考文献：
  名称：

  关于柔韧性在蛋白质-配体相互作用中的作用：p53四聚域的例子

  摘要：

  通过设计的配体识别蛋白质表面已成为药物发现中的一种有吸引力的方法。然而，蛋白质表面的可变性质和不规则行为违背了这一新的研究领域。易于理解的“锁匙式”模型远不是生物分子相互作用的理想范例，因此，有关蛋白质和配体在识别事件中如何行为的任何新发现都为这一过程铺平了道路。在这里，我们举例说明一个清晰的例子，说明蛋白质和配体的柔韧性增加如何导致大分子复合物的稳定性增加。对设计的柔性四胍盐杯[4]芳烃与蛋白p53（p53TD）及其天然突变体p53TD-R337H的四聚化域之间相互作用的生物物理研究表明，软盘突变域与配体的相互作用比与孔的相互作用更紧密。包装的野生型蛋白。此外，与以前报道的构象刚性杯芳烃类似物相比，柔性杯芳烃配体与野生型和突变蛋白结构域的亲和力更高。这些发现强调了对于小配体和大生物分子表面而言，灵活性在分子识别过程中的关键作用。与以前报道的构象刚性杯芳烃类似物相比，柔性杯芳烃配体与野生型

  DOI：

  10.1002/asia.201000938

文献信息

• On the Role of Flexibility in Protein-Ligand Interactions: the Example of p53 Tetramerization Domain
  作者：Susana Gordo、Vera Martos、Marta Vilaseca、Margarita Menéndez、Javier de Mendoza、Ernest Giralt

  DOI：10.1002/asia.201000938

  日期：2011.6.6

  well‐packed wild‐type protein. Moreover, the flexible calixarene ligand interacts with higher affinity to both wild‐type and mutated protein domains than a conformationally rigid calixarene analog previously reported. These findings underscore the crucial role of flexibility in molecular recognition processes, for both small ligands and large biomolecular surfaces.

  通过设计的配体识别蛋白质表面已成为药物发现中的一种有吸引力的方法。然而，蛋白质表面的可变性质和不规则行为违背了这一新的研究领域。易于理解的“锁匙式”模型远不是生物分子相互作用的理想范例，因此，有关蛋白质和配体在识别事件中如何行为的任何新发现都为这一过程铺平了道路。在这里，我们举例说明一个清晰的例子，说明蛋白质和配体的柔韧性增加如何导致大分子复合物的稳定性增加。对设计的柔性四胍盐杯[4]芳烃与蛋白p53（p53TD）及其天然突变体p53TD-R337H的四聚化域之间相互作用的生物物理研究表明，软盘突变域与配体的相互作用比与孔的相互作用更紧密。包装的野生型蛋白。此外，与以前报道的构象刚性杯芳烃类似物相比，柔性杯芳烃配体与野生型和突变蛋白结构域的亲和力更高。这些发现强调了对于小配体和大生物分子表面而言，灵活性在分子识别过程中的关键作用。与以前报道的构象刚性杯芳烃类似物相比，柔性杯芳烃配体与野生型
• Calix[4]arene-Based Receptors with Hydrogen-Bonding Groups Immersed into a Large Cavity
  作者：Evgueni Pinkhassik、Vladimir Sidorov、Ivan Stibor

  DOI：10.1021/jo9804543

  日期：1998.12.1

  A one-pot procedure, which combines the Ritter and Friedel-Crafts reactions, produced the first members of a new type of calix[4]arene-based receptors. The cavity in these receptors is formed by a calix[4]arene framework fixed in the cone conformation and bulky adamantyl or (and) phenylacetylene moieties. Amido and amino groups were used as potential hygrogen bond donors. Preliminary studies revealed interesting complexation properties, in particular, the tetrahedral recognition of water molecules performed by one of the receptors.
• Recognition Properties of Carboxylic Acid Bioisosteres: Anion Binding by Tetrazoles, Aryl Sulfonamides, and Acyl Sulfonamides on a Calix[4]arene Scaffold
  作者：Thomas Pinter、Subrata Jana、Rebecca J. M. Courtemanche、Fraser Hof

  DOI：10.1021/jo200031u

  日期：2011.5.20

  Tetrazoles and acyl sulfonamides are functional groups that are common in medicinal chemistry but virtually unexplored as recognition elements in supramolecular chemistry. We report here on the anion binding properties of these highly acidic N-H functional groups. We have prepared two new calixarene-based tetrazole-containing hosts, as well as new acetyl sulfonamide and benzoyl sulfonamide hosts. We also report on analogous hosts bearing the better-known aryl sulfonamide functional group as a point of comparison. We find that these hosts are competent anion binders and that the recognition of anions by these groups is highly dependent on their conformational preferences. We also report in detail on the preferred molecular shape of each acid bioisostere as determined by calculations and structural database surveys, and discuss how these shapes impact binding in the context of the reported hosts.
• Cyanocalix[4]arenes: synthesis, crystal structures and reactivity studies
  作者：Malcolm J. Applewhite、Delia A. Haynes、Gareth E. Arnott

  DOI：10.1080/10610278.2015.1121268

  日期：2016.6.2

  Herein, we describe an improved method to synthesise mono-, di- and tetra-cyanocalix[4]arene and report their crystal structure determinations. We also report our attempts to further functionalise the cyanocalix[4]arenes into dithiadiazolyl-calix[4]arenes, and propose a hypothesis as to why the cyano group on a calix[4]arene is an extremely challenging group to modify.

  摘要 在此，我们描述了一种合成单、二和四氰基杯[4]芳烃的改进方法，并报告了它们的晶体结构测定。我们还报告了我们将氰基杯[4]芳烃进一步官能化为二噻二唑基-杯[4]芳烃的尝试，并提出了一个假设，即为什么杯[4]芳烃上的氰基是一个极具挑战性的修饰基团。
• Heterodimerization Studies of Calix[4]arene Derivatives in Polar Solvents
  作者：Joshua S. Sasine、R. Elizabeth Brewster、Kevin L. Caran、Adrienne M. Bentley、Suzanne B. Shuker

  DOI：10.1021/ol060612+

  日期：2006.7.1

  Several calix[4]arene derivatives propylated on the lower rim and substituted on the upper rim with amino or carboxyl groups have been synthesized. Examples include calixarenes substituted with alanino (C- and N-linked), amino, carboxy, carboxyphenyl, and amidino groups. The self-assembly of these derivatized calixarenes into heterodimers has been studied by NMR in DMSO-d(6) or CD3OD with 5% aqueous phosphate buffer.