bis[(7,12-dimethoxyl-23-methoxycarbonyl)cholanyl-3-oxy]-N,N'-xylylene dicarbamate | 360042-73-5

• 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-dimethoxyl-23-methoxycarbonyl)cholanyl-3-oxy]-N,N'-xylylene dicarbamate
• 英文别名: bis[(methyl 7,12-dimethyl-24-carboxylate)-3-cholanyl]-N,N'-m-xylylene dicarbamate；methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[3-[[[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dimethoxy-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-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]methylcarbamoyloxy]-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-17-yl]pentanoate
• CAS: 360042-73-5
• 化学式: C₆₄H₁₀₀N₂O₁₂
• 分子量: 1089.5
• InChiKey: WUQFSXLOGBOFPC-XQHQDRHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  78
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis[(7,12-dimethoxyl-23-methoxycarbonyl)cholanyl-3-oxy]-N,N'-xylylene dicarbamate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以38%的产率得到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
• 作为产物：
  描述：

  胆酸甲酯 在 三乙烯二胺 、 硫酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 54.0h， 生成 bis[(7,12-dimethoxyl-23-methoxycarbonyl)cholanyl-3-oxy]-N,N'-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

• Artificial Ion Channels Showing Rectified Current Behavior
  作者：Chigusa Goto、Mika Yamamura、Akiharu Satake、Yoshiaki Kobuke

  DOI：10.1021/ja010761h

  日期：2001.12.1

  Voltage-dependent artificial ion channels 3 and 4 were synthesized. Two cholic acid derivatives were connected through a m-xylylene dicarbamate unit at 3-hydroxyl groups. Asymmetries were introduced by terminal hydrophilic groups, carboxylic acid and phosphoric acid for 3 and hydroxyl and carboxylic acid for 4. Under basic conditions, these headgroups in 3 and 4 are expected to be dissociate into -1/-2 (pH 8.2) and 0/-1 (pH 7.2), respectively. Single ion channel properties were examined by a planar bilayer lipid membrane method under symmetrical 500 mM KCl at pH 8.2 or 7.2. When 3 and 4 were introduced into the bilayer membrane under application of positive voltage (a positive-shift method), the current values at positive applied voltage were larger than the corresponding ones at the negative applied voltage. The current-voltage plots were fitted by curves through a zero point to show clear rectification properties. The direction of rectification could be controlled by positive- or negative-shift methods. Vectorial alignment of terminal headgroup charges by the voltage-shift incorporation is essential for giving voltage-dependent rectified ion channels.
• 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+.