12-bromo-1-[16-(12-bromododecanoyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecan-1-one | 165191-86-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 12-bromo-1-[16-(12-bromododecanoyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecan-1-one
• CAS: 165191-86-6
• 化学式: C₃₆H₆₈Br₂N₂O₆
• 分子量: 784.754
• InChiKey: VXURFNLUALEFGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  46.0
• 可旋转键数：
  22.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.54
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  12-bromo-1-[16-(12-bromododecanoyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecan-1-one 在 palladium on activated charcoal 硼烷 、 氢气 、 sodium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、482.63 kPa 条件下， 反应 168.0h， 生成 N,N'-bis[12-(diaza-18-crown-6)dodecyl]-18-crown-6
  参考文献：
  名称：

  Synthetic Models for Transmembrane Channels: Structural Variations That Alter Cation Flux

  摘要：

  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.

  DOI：

  10.1021/ja00134a011
• 作为产物：
  描述：

  12-溴十二烷酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 12-bromo-1-[16-(12-bromododecanoyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecan-1-one
  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

• The effect of twin-tailed sidearms on sodium cation transport in synthetic hydraphile cation channels
  作者：Hossein Shabany、Robert Pajewski、Ernesto Abel、Anindita Mukhopadhyay、George W. Gokel

  DOI：10.1002/jhet.5570380623

  日期：2001.11

  The preparation of novel tris(macrocycle)s that transport Na+ through phospholipid bilayers is reported. All of the reported structures have the following structural elements: sidechain-macrocycle-spacer-macro-cycle-spacer-macrocycle-sidechain. The overall extension of the channel system is defined by the lengths of the spacer chains. The flexible sidearms are thought to be aligned with the lipid axis

  据报道，新型Tris（大环）可通过磷脂双层转运Na +。所有报告的结构均具有以下结构元素：侧链-大环-间隔子-大环-循环-大环-侧链。通道系统的整体延伸范围由间隔链的长度决定。柔性侧臂被认为与脂质轴对齐并且与间隔链相反。在一定程度上，间隔链有助于结构的组织以及将含阳离子的孔与周围的脂质链隔离，更多的疏水链有望增强阳离子的运输。C 12 H 25 （CH 2）12 （CH2）12 Ç 12 ħ 25，1，用（C 12 H ^ 25）2 N（CH 2）2 （CH 2）12 （CH 2）12 （CH 2） 2N（C 12 H ^ 25）2，图11，示出了的Na +转运，着实增强。
• 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.
• Fluorobenzyl Terminal Residues as Probes of Function in Tris(macrocycle) Channels:  Evidence from NMR and Planar Bilayer Conductance Studies
  作者：Clare L. Murray、Eric S. Meadows、Oscar Murillo、George W. Gokel

  DOI：10.1021/ja971325r

  日期：1997.8.1
• A Comparison of Phenyl- and Naphthyl-substituted tris(Macrocycle), Cation-conducting Channels to Assess the Effect of Extended Aromaticity
  作者：Glenn E.M. Maguire、Eric S. Meadows、Clare L. Murray、George W. Gokel

  DOI：10.1016/s0040-4039(97)01458-5

  日期：1997.9

  Two sodium-cation-conducting, tris(macrocycle) channels, differing only in the size of the terminal aryl groups, have been prepared, characterized, and shown by the planar bilayer conductance method to exhibit qualitative differences in channel activity attributable to the pi-electron surface area difference. (C) 1997 Elsevier Science Ltd.