N,N'-bis(11-carboxyundecyl)-4,13-diaza-18-crown-6 | 179084-77-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N'-bis(11-carboxyundecyl)-4,13-diaza-18-crown-6
• 英文别名: 12-[16-(11-Carboxyundecyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecanoic acid；12-[16-(11-carboxyundecyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecanoic acid
• CAS: 179084-77-6
• 化学式: C₃₆H₇₀N₂O₈
• 分子量: 658.96
• InChiKey: ZJNZKZKCQYEKEG-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C
• 沸点：
  767.4±55.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  46
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N'-bis(11-carboxyundecyl)-4,13-diaza-18-crown-6 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 反应 2.0h， 生成 12-[16-(11-Chlorocarbonyl-undecyl)-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadec-7-yl]-dodecanoyl chloride
  参考文献：
  名称：

  增强具有共价连接头基的合成亲水通道中的阳离子传输

  摘要：

  已经制备了一种新型的五大环主体分子，其中四个对称等效的二氮杂冠醚导致钠离子转运显着增强，通过磷脂双层，相对于缺乏第四冠的开链类似物。

  DOI：

  10.1039/b005436o
• 作为产物：
  描述：

  12-溴十二烷酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 sodium carbonate 、 potassium iodide 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 24.0h， 生成 N,N'-bis(11-carboxyundecyl)-4,13-diaza-18-crown-6
  参考文献：
  名称：

  活细胞中电生理方法记录的合成离子通道活性

  摘要：

  Hydraphiles 是合成离子通道，使用冠醚作为入口并跨越磷脂双层膜。这些化合物的质子和钠阳离子传输已在脂质体和平面双层中得到证实。在目前的工作中，全细胞膜片钳实验表明亲水胶整合到人胚胎肾 (HEK 293) 细胞的膜中并显着增加膜电导。膜通透性的改变是可逆的，研究中的细胞在实验过程中仍然至关重要。太短（C(8)-苄基通道）无法跨越双层或由于中央继电器缺陷而处于非活动状态的对照化合物不会引起类似的电导增加。对照实验证实非活性通道类似物不显示非特异性效应，例如激活天然通道。

  DOI：

  10.1021/ja046626x

文献信息

• The influence of varied amide bond positions on hydraphile ion channel activity
  作者：Michelle E. Weber、Wei Wang、Sarah E. Steinhardt、Michael R. Gokel、W. Matthew Leevy、George W. Gokel

  DOI：10.1039/b510863m

  日期：——

  Hydraphile compounds have been prepared in which certain of the amine nitrogens have been replaced by amide residues. The amide bonds are present either in the sidearm, the side chain, or the central relay. Sodium cation transport through phospholipid vesicles mediated by each hydraphile was assessed. All of the amide-containing hydraphiles showed increased levels of Na(+) transport compared to the

  已经制备了亲水化合物，其中某些胺氮已被酰胺残基取代。酰胺键存在于侧臂、侧链或中央中继中。评估了由每个亲水物介导的通过磷脂囊泡的钠阳离子转运。与母体化合物相比，所有含酰胺的亲水物都显示出增加的 Na(+) 运输水平，但观察到侧臂胺到酰胺置换的速率增加最显着。我们将这种增强归因于双层中侧臂的稳定性，以实现更好的离子传导构象。用大肠杆菌和枯草芽孢杆菌对酰胺亲水菌进行的生物学研究表明，只有后者才具有显着的毒性。更远，
• Enhancement of cation transport in synthetic hydraphile channels having covalently-linked headgroups
  作者：Hossein Shabany、George W. Gokel

  DOI：10.1039/b005436o

  日期：——

  A novel, pentamacrocyclic host molecule has been prepared in which four symmetry-equivalent diazacrown ethers lead to a dramatic enhancement in Na+ transport, across a phospholipid bilayer, relative to open-chained analogs lacking the fourth crown.

  已经制备了一种新型的五大环主体分子，其中四个对称等效的二氮杂冠醚导致钠离子转运显着增强，通过磷脂双层，相对于缺乏第四冠的开链类似物。
• Synthetic Transmembrane Channels:  Functional Characterization Using Solubility Calculations, Transport Studies, and Substituent Effects
  作者：Oscar Murillo、Iwao Suzuki、Ernesto Abel、Clare L. Murray、Eric S. Meadows、Takashi Jin、George W. Gokel

  DOI：10.1021/ja962694a

  日期：1997.6.1

  Dibenzyldiaza-18-crown-6 (PhCH2[N18N]CH2Ph, 1), di(dodecyldiaza-18-crown-6 (C12H25[N18N]C12H25, 2), HOOC(CH2)(11)[N18N](CH2)(11)COOH (3), (18N)(CH2)(12)[N18N](CH2)(12)[N18] (4), [N18N](CH2)(12)[N18N](CH2)(12)[N18N] (5), C12H25[N18N](CH2)(12)[N18N](CH2)(12)[N18N]C12H25 (6), PhCH2[N18N](CH2)(12)[N18N](CH2)(12)[N18N]CH2Ph (7), 4-(p-MeOC6H4CH2[N18N]C-12)(2)[N18N] (8), (p-NO2C6H4CH2[N18N]C-12)(2)[N18N] (9), and [chol-O-(CH2)(2)[N18N]C-12](2)[N18N] (10) were studied. Octanol-water partition coefficients were determined for 1, 6, 7, 8, 10, and 3-cholestanyl-OCOCH2[N18N](CH2)(12)[N18N](CH2)(12)[N18N]COCH2O-3-cholestanyl (11). All were found to favor octanol, and by implication the phospholipid bilayer membrane, by at least 10(4)-fold. Transport of Na+ was assessed in both a phospholipid bilayer and in a bulk CHCl3 membrane phase. Addition of ionophores to the latter was found in some cases to strongly enhance CHCl3 phase hydration. An attempt to correlate transport rates determined in the two systems failed, suggesting that the carrier mechanism, required in the CHCl3 phase, does not apply to the tris(macrocyclic) compounds in the bilayer. Sodium transport rates were also assessed for these compounds by using the bilayer clamp technique. Although Na+ flux rates thus determined for 7-9 in the phospholipid bilayer did not correlate with results obtained by the Na-23-NMR technique, the traces are similar to those obtained with protein channels, further supporting the function of tris(macrocycle)s as channel formers.
• Heterocyclic Amide Hydraphile Synthetic Cation Transporters
  作者：George W. Gokel、Wei Wang、Carl R. Yamnitz

  DOI：10.3987/com-07-s(u)62

  日期：——

  A family of hydraphile ionophores has been prepared in which various approximately CH(2)N approximately to approximately CON approximately replacements have been made to assess the effect on Na(+) transport through phospholipid bilayers. When the central relay (see graphical abstract) was a third macrocycle, symmetrical carbonyl for methylene replacements enhanced activity, but the presence of four or six amide residues diminished transport. When a pair of amides was incorporated into compounds having a 4,4'-bipiperidyl central relay, both significant increases and decreases were observed depending upon the amide positions. The presence of amides alters both the donor group type and strength and the conformation of the structural unit in which it occurs. These changes are shown to depend on the liposomes in which the Na(+) release studies were conducted. These changes are shown to affect the toxicity of the hydraphiles to E. coli.
• Synthetic Ion Channel Activity Documented by Electrophysiological Methods in Living Cells
  作者：W. Matthew Leevy、James E. Huettner、Robert Pajewski、Paul H. Schlesinger、George W. Gokel

  DOI：10.1021/ja046626x

  日期：2004.12.1

  Hydraphiles are synthetic ion channels that use crown ethers as entry portals and that span phospholipid bilayer membranes. Proton and sodium cation transport by these compounds has been demonstrated in liposomes and planar bilayers. In the present work, whole cell patch clamp experiments show that hydraphiles integrate into the membranes of human embryonic kidney (HEK 293) cells and significantly

  Hydraphiles 是合成离子通道，使用冠醚作为入口并跨越磷脂双层膜。这些化合物的质子和钠阳离子传输已在脂质体和平面双层中得到证实。在目前的工作中，全细胞膜片钳实验表明亲水胶整合到人胚胎肾 (HEK 293) 细胞的膜中并显着增加膜电导。膜通透性的改变是可逆的，研究中的细胞在实验过程中仍然至关重要。太短（C(8)-苄基通道）无法跨越双层或由于中央继电器缺陷而处于非活动状态的对照化合物不会引起类似的电导增加。对照实验证实非活性通道类似物不显示非特异性效应，例如激活天然通道。