5-[25,26,27,28-tetrapropoxy-11,17,23-tris(2H-tetrazol-5-yl)-5-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]-2H-tetrazole | 1297532-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[25,26,27,28-tetrapropoxy-11,17,23-tris(2H-tetrazol-5-yl)-5-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]-2H-tetrazole
• CAS: 1297532-73-0
• 化学式: C₄₄H₄₈N₁₆O₄
• 分子量: 864.97
• InChiKey: QRTJLJUKESLWKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  64
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  255
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  25,26,27,28-tetrakis(propoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene 在 sodium azide 、 zinc dibromide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以95%的产率得到5-[25,26,27,28-tetrapropoxy-11,17,23-tris(2H-tetrazol-5-yl)-5-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]-2H-tetrazole
  参考文献：
  名称：

  Recognition Properties of Carboxylic Acid Bioisosteres: Anion Binding by Tetrazoles, Aryl Sulfonamides, and Acyl Sulfonamides on a Calix[4]arene Scaffold

  摘要：

  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.

  DOI：

  10.1021/jo200031u

文献信息

• 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.