bis(7,12-dimethyl-24-hydroxy-3-cholanyl)-N,N'-m-xylylene dicarbamate | 360042-74-6

• 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: bis(7,12-dimethyl-24-hydroxy-3-cholanyl)-N,N'-m-xylylene dicarbamate
• 英文别名: [(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-5-hydroxypentan-2-yl]-7,12-dimethoxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[[3-[[[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-5-hydroxypentan-2-yl]-7,12-dimethoxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]methyl]phenyl]methyl]carbamate
• CAS: 360042-74-6
• 化学式: C₆₂H₁₀₀N₂O₁₀
• 分子量: 1033.48
• InChiKey: YSEHXCNLUDMBMG-KDYYDRIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  74
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  氯化甜菜碱酰氯 、 bis(7,12-dimethyl-24-hydroxy-3-cholanyl)-N,N'-m-xylylene dicarbamate 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以2%的产率得到bis[7,12-dimethyl-24-(N,N,N-trimethylethanaminium-2-carboxylate)-3-cholanyl]-N,N'-m-xylylene dicarbamate dichloride
  参考文献：
  名称：

  Transmembrane Ion Channels Constructed of Cholic Acid Derivatives

  摘要：

  A new class of supramolecular transmembrane ion channels was prepared by linking two amphiphilic cholic acid methyl ethers through biscarbamate bonds to afford bis(7,12-dimethyl-24-carboxy-3-cholanyl)-N,N'-xylylene dicarbamate 2 and bis[7,12-dimethyl-24-(N,N,N-trimethylethanaminium-2-carboxylate)-3-cholanyl]-N,N'-xylylene dicarbamate dichloride 3. When incorporated into a planar bilayer membrane, both compounds showed stable (lasting 10 ms to 10 s) single ion channel currents. Only limited numbers of relatively small conductances were characterized for these channels (5-20 pS for 2 and 5-10 pS for 3, 10 and 17 pS for 2, and 9 pS for 3 in particular). Both channels were cation selective, and permeability ratios of potassium cation to chloride anion were 17 and 7.9 for 2 and 3, respectively, reflecting the difference in ionic species of the headgroup. Both channels 2 and 3 showed significant potassium selectivity over sodium by a factor of 3.1 and 3.2, respectively. No Li+ currents were observed for 2, showing sharp discrimination between Na+ or K+.

  DOI：

  10.1021/jo010208i
• 作为产物：
  描述：

  胆酸甲酯 在 三乙烯二胺 、 锂硼氢 、 硫酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 63.0h， 生成 bis(7,12-dimethyl-24-hydroxy-3-cholanyl)-N,N'-m-xylylene dicarbamate
  参考文献：
  名称：

  Transmembrane Ion Channels Constructed of Cholic Acid Derivatives

  摘要：

  A new class of supramolecular transmembrane ion channels was prepared by linking two amphiphilic cholic acid methyl ethers through biscarbamate bonds to afford bis(7,12-dimethyl-24-carboxy-3-cholanyl)-N,N'-xylylene dicarbamate 2 and bis[7,12-dimethyl-24-(N,N,N-trimethylethanaminium-2-carboxylate)-3-cholanyl]-N,N'-xylylene dicarbamate dichloride 3. When incorporated into a planar bilayer membrane, both compounds showed stable (lasting 10 ms to 10 s) single ion channel currents. Only limited numbers of relatively small conductances were characterized for these channels (5-20 pS for 2 and 5-10 pS for 3, 10 and 17 pS for 2, and 9 pS for 3 in particular). Both channels were cation selective, and permeability ratios of potassium cation to chloride anion were 17 and 7.9 for 2 and 3, respectively, reflecting the difference in ionic species of the headgroup. Both channels 2 and 3 showed significant potassium selectivity over sodium by a factor of 3.1 and 3.2, respectively. No Li+ currents were observed for 2, showing sharp discrimination between Na+ or K+.

  DOI：

  10.1021/jo010208i

文献信息

• Transmembrane Ion Channels Constructed of Cholic Acid Derivatives
  作者：Yoshiaki Kobuke、Takeshi Nagatani

  DOI：10.1021/jo010208i

  日期：2001.7.1

  A new class of supramolecular transmembrane ion channels was prepared by linking two amphiphilic cholic acid methyl ethers through biscarbamate bonds to afford bis(7,12-dimethyl-24-carboxy-3-cholanyl)-N,N'-xylylene dicarbamate 2 and bis[7,12-dimethyl-24-(N,N,N-trimethylethanaminium-2-carboxylate)-3-cholanyl]-N,N'-xylylene dicarbamate dichloride 3. When incorporated into a planar bilayer membrane, both compounds showed stable (lasting 10 ms to 10 s) single ion channel currents. Only limited numbers of relatively small conductances were characterized for these channels (5-20 pS for 2 and 5-10 pS for 3, 10 and 17 pS for 2, and 9 pS for 3 in particular). Both channels were cation selective, and permeability ratios of potassium cation to chloride anion were 17 and 7.9 for 2 and 3, respectively, reflecting the difference in ionic species of the headgroup. Both channels 2 and 3 showed significant potassium selectivity over sodium by a factor of 3.1 and 3.2, respectively. No Li+ currents were observed for 2, showing sharp discrimination between Na+ or K+.