3-(10,11-二氢-5H-二苯并(a,d)环庚烯-5-亚基)-N-beta-D-吡喃葡糖基-N,N-二甲基-1-丙铵氢氧化物内盐 | 112806-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 中文名称: 3-(10,11-二氢-5H-二苯并(a,d)环庚烯-5-亚基)-N-beta-D-吡喃葡糖基-N,N-二甲基-1-丙铵氢氧化物内盐
• 英文名称: Amitriptyline N-glucuronide
• 英文别名: (2S,3S,4S,5R,6R)-6-[dimethyl-[3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propyl]azaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 112806-33-4
• 化学式: C₂₆H₃₁NO₆
• 分子量: 453.535
• InChiKey: WXMXRAPAGYPAJI-ARXROMJUSA-N

物化性质

• 熔点：
  >130°C (dec.)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• WGK Germany：
  2

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5S,6S)-N-(3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)propyl)-3,4,5-tris(isobutyryloxy)-6-(methoxycarbonyl)-N,N-dimethyltetrahydro-2H-pyran-2-aminium trifluoromethanesulfonate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以0.064 g的产率得到3-(10,11-二氢-5H-二苯并(a,d)环庚烯-5-亚基)-N-beta-D-吡喃葡糖基-N,N-二甲基-1-丙铵氢氧化物内盐
  参考文献：
  名称：

  A convenient new synthesis of quaternary ammonium glucuronides of drug molecules

  摘要：

  N-Glucuronides, of various Structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+-glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.113

文献信息

• A convenient new synthesis of quaternary ammonium glucuronides of drug molecules
  作者：Lisa Iddon、Ryan A. Bragg、John R. Harding、Andrew V. Stachulski

  DOI：10.1016/j.tet.2009.10.113

  日期：2010.1

  N-Glucuronides, of various Structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+-glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification. (C) 2009 Elsevier Ltd. All rights reserved.