triphenoxyacetic acid | 824424-49-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: triphenoxyacetic acid
• 英文别名: 2-[2-[[2-(Carboxymethoxy)-3-[[2-(carboxymethoxy)phenyl]methyl]phenyl]methyl]phenoxy]acetic acid
• CAS: 824424-49-9
• 化学式: C₂₆H₂₄O₉
• 分子量: 480.471
• InChiKey: RUCAWZGRBPYFKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  triphenoxyacetic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 [2,6-Bis-(2-chlorocarbonylmethoxy-benzyl)-phenoxy]-acetyl chloride
  参考文献：
  名称：

  Chloride Transport Across Lipid Bilayers and Transmembrane Potential Induction by an Oligophenoxyacetamide

  摘要：

  This contribution describes the discovery and properties of a synthetic, low-molecular weight compound that transports Cl- across bilayer membranes. Such compounds have potential as therapeutics for cystic fibrosis and cancer. The H+/Cl- co-transport activities of acyclic tetrabutylamides 1-6 were compared by using a pH-stat assay with synthetic EYPC liposomes. The ion transport activity of the most active compound, trimer 3, was an order of magnitude greater than that of calix[4]arene tetrabutylamide C1 a macrocycle known to function as a synthetic ion channel. Trimer 3 has an unprecedented function for a synthetic compound, as it induces a stable potential in liposomes experiencing a transmembrane Cl-/SO42- gradient. Data from both pH-stat and 35Cl NMR experiments indicate that 3 co-transports H+/Cl-. Although 3 transports both Cl- and H+ the overall process is not electrically silent. Thus, trimer 3 induces a stable potential in LUVs due to a transmembrane anionic gradient. The ability of trimer 3 to transport Cl-, to maintain a transmembrane potential, along with its high activity at uM concentrations, its low molecular weight, and its simple preparation, make this compound a valuable lead in drug development for diseases caused by Cl- transport malfunction.

  DOI：

  10.1021/ja029372t
• 作为产物：
  描述：

  tris-(ethylphenoxy acetate) 在 氢氧化钾 、 水 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 triphenoxyacetic acid
  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。
• US7355074B2
  申请人：——

  公开号：US7355074B2

  公开（公告）日：2008-04-08
• Chloride Transport Across Lipid Bilayers and Transmembrane Potential Induction by an Oligophenoxyacetamide
  作者：Vladimir Sidorov、Frank W. Kotch、Jennifer L. Kuebler、Yiu-Fai Lam、Jeffery T. Davis

  DOI：10.1021/ja029372t

  日期：2003.3.1

  This contribution describes the discovery and properties of a synthetic, low-molecular weight compound that transports Cl- across bilayer membranes. Such compounds have potential as therapeutics for cystic fibrosis and cancer. The H+/Cl- co-transport activities of acyclic tetrabutylamides 1-6 were compared by using a pH-stat assay with synthetic EYPC liposomes. The ion transport activity of the most active compound, trimer 3, was an order of magnitude greater than that of calix[4]arene tetrabutylamide C1 a macrocycle known to function as a synthetic ion channel. Trimer 3 has an unprecedented function for a synthetic compound, as it induces a stable potential in liposomes experiencing a transmembrane Cl-/SO42- gradient. Data from both pH-stat and 35Cl NMR experiments indicate that 3 co-transports H+/Cl-. Although 3 transports both Cl- and H+ the overall process is not electrically silent. Thus, trimer 3 induces a stable potential in LUVs due to a transmembrane anionic gradient. The ability of trimer 3 to transport Cl-, to maintain a transmembrane potential, along with its high activity at uM concentrations, its low molecular weight, and its simple preparation, make this compound a valuable lead in drug development for diseases caused by Cl- transport malfunction.