(1,4,10,13-Tetraoxa-7,16-diaza-cyclooctadec-7-yl)-acetic acid (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester | 268559-35-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1,4,10,13-Tetraoxa-7,16-diaza-cyclooctadec-7-yl)-acetic acid (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
• CAS: 268559-35-9
• 化学式: C₄₁H₇₄N₂O₆
• 分子量: 691.048
• InChiKey: NSRMXDXCAXQCBG-DRDDINBJSA-N

物化性质

• 沸点：
  729.1±60.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  49.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  78.49
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,12-二溴十二烷 、 (1,4,10,13-Tetraoxa-7,16-diaza-cyclooctadec-7-yl)-acetic acid (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 sodium carbonate 、 potassium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 1.5h， 以20%的产率得到[16-(12-Bromo-dodecyl)-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadec-7-yl]-acetic acid (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  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：

  3β-胆甾烷醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 sodium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 苯 为溶剂， 反应 39.0h， 生成 (1,4,10,13-Tetraoxa-7,16-diaza-cyclooctadec-7-yl)-acetic acid (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  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