calix[4]arene octabutylamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: calix[4]arene octabutylamide
• 英文别名: N,N-dibutyl-2-[[26,27,28-tris[2-(dibutylamino)-2-oxoethoxy]-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl]oxy]acetamide
• 化学式: C₆₈H₁₀₀N₄O₈
• 分子量: 1101.56
• InChiKey: QKCBVEFZRRIDCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  80
• 可旋转键数：
  36
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  25,26,27,28-tetrakis(carboxymethoxy)calix[4]arene 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.5h， 生成 calix[4]arene octabutylamide
  参考文献：
  名称：

  Compounds having aromatic rings and side-chain amide-functionality and a method for transporting monovalent anions across biological membranes using the same

  摘要：

  含有至少两个芳香环的化合物，这些芳香环以共价键结合在一起，每个芳香环至少含有一个氧乙酰胺基侧链，该化合物能够在脂质双分子层上形成氯离子通道，并在脂质双分子层上运输氯离子。

  公开号：

  US20050009921A1

文献信息

• Compounds having aromatic rings and side-chain amide-functionality and a method for transporting monovalent anions across biological membranes using the same
  申请人：Davis T. Jeffery

  公开号：US20050009921A1

  公开（公告）日：2005-01-13

  A compound containing at least two aromatic rings covalently bonded together, with each aromatic ring containing at least one oxyacetamide-based side chain, the compound being capable of forming a chloride ion channel across a lipid bilayer, and transporting chloride ion across the lipid bilayer.

  含有至少两个芳香环的化合物，这些芳香环以共价键结合在一起，每个芳香环至少含有一个氧乙酰胺基侧链，该化合物能够在脂质双分子层上形成氯离子通道，并在脂质双分子层上运输氯离子。
• Ion Channel Formation from a Calix[4]arene Amide That Binds HCl
  作者：Vladimir Sidorov、Frank W. Kotch、Galya Abdrakhmanova、Robert Mizani、James C. Fettinger、Jeffery T. Davis

  DOI：10.1021/ja012338e

  日期：2002.3.1

  The ion transport activity of calix[4]arene tetrabutylamide 1,3-alt 2 was studied in liposomes, planar lipid bilayers, and HEK-293 cells. These experiments, when considered together with H-1 NMR and X-ray crystallography data, indicate that calix[4]arene tetrabutylamide 2 (1) forms ion channels in bilayer membranes, (2) mediates ion transport across cell membranes at positive holding potential, (3) alters the pH inside liposomes experiencing a Cl- gradient, and (4) shows a significant Cl-/SO42- transport selectivity. An analogue, calix[4]arene tetramethylamide 1, self-assembles in the presence of HCl to generate solid-state structures with chloride-filled and water-filled channels. Structure-activity studies indicate that the hydrophobicity, amide substitution, and macrocyclic framework of the calixarene are essential for HCl binding and transport. Calix[4]arene tetrabutylamide 2 is a rare example of an anion-dependent, synthetic ion channel.