N,N''-bis{12-[N-(N'-dodecyl)diaza-18-crown-6]dodecyl}diaza-18-crown-6 | 124890-69-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N''-bis{12-[N-(N'-dodecyl)diaza-18-crown-6]dodecyl}diaza-18-crown-6
• 英文别名: N,N'-bis<12-dodecyl>-diaza-18-crown-6；N,N'-bis<12-dodecyl>-4,13-diaza-18-crown-6；N,N'-bis<12-(N'-dodedecyldiaza-18-crown-6)-dodecyl>diaza-18-crown-6；7,16-Bis[12-(16-dodecyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 124890-69-3
• 化学式: C₈₄H₁₇₀N₆O₁₂
• 分子量: 1456.31
• InChiKey: QFNHHAQBJRTTOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.5
• 重原子数：
  102
• 可旋转键数：
  48
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  1-[16-[12-[16-[12-(16-Dodecanoyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecan-1-one 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以67%的产率得到N,N''-bis{12-[N-(N'-dodecyl)diaza-18-crown-6]dodecyl}diaza-18-crown-6
  参考文献：
  名称：

  不同酰胺键位置对亲水离子通道活性的影响。

  摘要：

  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，

  DOI：

  10.1039/b510863m

文献信息

• 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。
• Synthetic Models for Transmembrane Channels: Structural Variations That Alter Cation Flux
  作者：Oscar Murillo、Shigeru Watanabe、Akio Nakano、George W. Gokel

  DOI：10.1021/ja00134a011

  日期：1995.7

  Twelve novel bis- or tris(macrocyclic) compounds have been designed as models for cation-conducting channels that function in phospholipid bilayer vesicle membranes. In general, the channel model systems have the structure ''sidearm-crown-spacer-crown-spacer-crown-sidearm'', although certain features have been altered from compound to compound to assess the structure-activity relationship. Two additional compounds have been prepared exclusively as controls. The ionophores have been incorporated into the membranes either by warming the compound with the preformed vesicle or by incorporation during vesicle formation. The two methods gave identical results within experimental error. Cation flux was assessed by two different analytical methods. In one case, the fluorescent dye pyranine was encapsulated within vesicles containing ionophore. Proton transport was then monitored by changes in dye fluorescence with time following an acid pulse. Ionophoretic activity far most of the compounds was studied using a dynamic NMR method in which the flux rate of Na-23(+) through the bilayer was monitored. All NMR studies were done in conjunction with gramicidin as a control to minimize experimental variations from run to run. Several of the synthetic ionophores showed cation conduction of as much as 40% of the activity of gramicidin. Apparently, small structural changes significantly altered flux rates and two known carriers closely related to the channel formers failed to exhibit measurable transport under comparable conditions.
• Nakano, Akio; Xie, Qingshan; Mallen, Jesus V., Journal of the American Chemical Society, 1990, vol. 112, # 3, p. 1287 - 1289
  作者：Nakano, Akio、Xie, Qingshan、Mallen, Jesus V.、Echegoyen, Luis、Gokel, George W.

  DOI：——

  日期：——
• 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，