N,N'-bis(4-[8-(4-tert-butoxycarbonylamidobenzoyl)octyl]carboxyphenyl)terephthalamide | 501088-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis(4-[8-(4-tert-butoxycarbonylamidobenzoyl)octyl]carboxyphenyl)terephthalamide
• 英文别名: 8-[4-[(2-Methylpropan-2-yl)oxycarbonylamino]benzoyl]oxyoctyl 4-[[4-[[4-[8-[4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]oxyoctoxycarbonyl]phenyl]carbamoyl]benzoyl]amino]benzoate
• CAS: 501088-79-5
• 化学式: C₆₂H₇₄N₄O₁₄
• 分子量: 1099.29
• InChiKey: NEAMFFFCYOZNNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  80
• 可旋转键数：
  36
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  240
• 氢给体数：
  4
• 氢受体数：
  14

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	[8-(4-tert-butoxycarbonylamidobenzoyl)octyl] 4-aminobenzoate	501088-90-0	C27H36N2O6	484.593
  ——	8-hydroxyoctyl 4-tert-butoxycarbonylamidobenzoate	501088-70-6	C20H31NO5	365.47
  ——	[8-(4-tert-butoxycarbonylamidobenzoyl)octyl] 4-nitrobenzoate	501088-77-3	C27H34N2O8	514.576
  N-BOC-4-氨基苯甲酸	4-(N-tert-butoxycarbonyl)aminobenzoic acid	66493-39-8	C12H15NO4	237.255

反应信息

• 作为反应物：
  描述：

  N,N'-bis(4-[8-(4-tert-butoxycarbonylamidobenzoyl)octyl]carboxyphenyl)terephthalamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以80%的产率得到N,N'-bis(4-[8-(4-amidobenzoyl)octyl]carboxyphenyl)terephthalamide
  参考文献：
  名称：

  Ion Channels from Linear and Branched Bola-Amphiphiles

  摘要：

  The synthesis and characterization of the ion channel activity of three new bola-amphiphiles is described. These compounds are conceptually derived from a previously reported bis-cyclophane bola-amphiphile through opening of the cyclophanes to acyclic structures and were found to readily form ion channels in planar bilayer membranes as assessed by bilayer clamp single-channel analysis. All three compounds behaved very similarly: the dominant channels formed by all three are Ohmic with specific conductance of 10 +/- 1 pS (NaCl electrolyte) and 39 +/- 1 pS (CsCl electrolyte). Singleion permeability ratios, determined from dissymmetric electrolyte experiments, showed the selectivity P(Cs+) > P(Na+) > P(Cl-). Less frequently, lower conductance channels were also observed to act independently of the dominant channels. The lifetimes of the dominant channels range from 70 to 280 ms for the three compounds with some very long-lived openings (20-40 s) observed for two of the three. The lower conductance states have shorter lifetimes. This study demonstrates that bis-macrocyclic compounds are not essential for channel formation by bola-amphiphiles, and opens a new class of channel-forming compounds for structure- activity optimization.

  DOI：

  10.1021/jo026415f
• 作为产物：
  描述：

  N-BOC-4-氨基苯甲酸 在 palladium on activated charcoal 四甲基氢氧化铵 、 氢气 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 50.0~90.0 ℃ 、344.75 kPa 条件下， 反应 186.0h， 生成 N,N'-bis(4-[8-(4-tert-butoxycarbonylamidobenzoyl)octyl]carboxyphenyl)terephthalamide
  参考文献：
  名称：

  Ion Channels from Linear and Branched Bola-Amphiphiles

  摘要：

  The synthesis and characterization of the ion channel activity of three new bola-amphiphiles is described. These compounds are conceptually derived from a previously reported bis-cyclophane bola-amphiphile through opening of the cyclophanes to acyclic structures and were found to readily form ion channels in planar bilayer membranes as assessed by bilayer clamp single-channel analysis. All three compounds behaved very similarly: the dominant channels formed by all three are Ohmic with specific conductance of 10 +/- 1 pS (NaCl electrolyte) and 39 +/- 1 pS (CsCl electrolyte). Singleion permeability ratios, determined from dissymmetric electrolyte experiments, showed the selectivity P(Cs+) > P(Na+) > P(Cl-). Less frequently, lower conductance channels were also observed to act independently of the dominant channels. The lifetimes of the dominant channels range from 70 to 280 ms for the three compounds with some very long-lived openings (20-40 s) observed for two of the three. The lower conductance states have shorter lifetimes. This study demonstrates that bis-macrocyclic compounds are not essential for channel formation by bola-amphiphiles, and opens a new class of channel-forming compounds for structure- activity optimization.

  DOI：

  10.1021/jo026415f

文献信息

• Ion Channels from Linear and Branched Bola-Amphiphiles
  作者：P. K. Eggers、T. M. Fyles、K. D. D. Mitchell、T. Sutherland

  DOI：10.1021/jo026415f

  日期：2003.2.1

  The synthesis and characterization of the ion channel activity of three new bola-amphiphiles is described. These compounds are conceptually derived from a previously reported bis-cyclophane bola-amphiphile through opening of the cyclophanes to acyclic structures and were found to readily form ion channels in planar bilayer membranes as assessed by bilayer clamp single-channel analysis. All three compounds behaved very similarly: the dominant channels formed by all three are Ohmic with specific conductance of 10 +/- 1 pS (NaCl electrolyte) and 39 +/- 1 pS (CsCl electrolyte). Singleion permeability ratios, determined from dissymmetric electrolyte experiments, showed the selectivity P(Cs+) > P(Na+) > P(Cl-). Less frequently, lower conductance channels were also observed to act independently of the dominant channels. The lifetimes of the dominant channels range from 70 to 280 ms for the three compounds with some very long-lived openings (20-40 s) observed for two of the three. The lower conductance states have shorter lifetimes. This study demonstrates that bis-macrocyclic compounds are not essential for channel formation by bola-amphiphiles, and opens a new class of channel-forming compounds for structure- activity optimization.