6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸,硫酸 | 88980-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸,硫酸
• 英文名称: 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrogen sulfate
• 英文别名: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid;sulfuric acid；6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid;sulfuric acid
• CAS: 88980-04-5
• 化学式: C₁₂H₁₅NO₄*H₂O₄S
• 分子量: 335.335
• InChiKey: SKFIUZYGGSXCON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸,硫酸 在 盐酸 作用下， 反应 72.0h， 以81.5%的产率得到6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸甲酯盐酸盐
  参考文献：
  名称：

  Biomimetic approach to potential benzodiazepine receptor agonists and antagonists

  摘要：

  Several beta-carbolines, isoquinolines, imidazopyridines , and canthin -6-ones prepared in biomimetic fashion were tested for their ability to bind to the benzodiazepine receptor. Methyl isoquinoline-3-carboxylate, methyl 6,7- dimethoxyisoquinoline -3-carboxylate (3b) 1-phenyl-3- carbomethoxyimidazopyridine , (6B,) and canthin -6- one ( 13a ) bound with moderate affinities, while 2- carbomethoxycanthin -6- one ( 13b ) bound to benzodiazepine receptors with an affinity comparable to several pharmacologically active benzodiazepines. The potency of 13b suggests that the benzodiazepine receptor(s) can tolerate substitution at positions 1 and 9 of a beta-carboline without loss of activity if the substituents are trigonal and maintain a planar topography. Moreover, displacement of the carbonyl group by two atoms from the aromatic ring (C) of the beta-carboline skeleton caused a marked decrease in binding to the benzodiazepine receptor. This observation supports the hypothesis that maximum binding affinity of beta-carbolines is achieved when the carbonyl group at position 3 is attached directly to the aromatic pyridine ring.

  DOI：

  10.1021/jm00371a002
• 作为产物：
  描述：

  聚合甲醛 、 2-硝基苯磺酰胺 在 硫酸 作用下， 反应 24.0h， 以50.7%的产率得到6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸,硫酸
  参考文献：
  名称：

  Biomimetic approach to potential benzodiazepine receptor agonists and antagonists

  摘要：

  Several beta-carbolines, isoquinolines, imidazopyridines , and canthin -6-ones prepared in biomimetic fashion were tested for their ability to bind to the benzodiazepine receptor. Methyl isoquinoline-3-carboxylate, methyl 6,7- dimethoxyisoquinoline -3-carboxylate (3b) 1-phenyl-3- carbomethoxyimidazopyridine , (6B,) and canthin -6- one ( 13a ) bound with moderate affinities, while 2- carbomethoxycanthin -6- one ( 13b ) bound to benzodiazepine receptors with an affinity comparable to several pharmacologically active benzodiazepines. The potency of 13b suggests that the benzodiazepine receptor(s) can tolerate substitution at positions 1 and 9 of a beta-carboline without loss of activity if the substituents are trigonal and maintain a planar topography. Moreover, displacement of the carbonyl group by two atoms from the aromatic ring (C) of the beta-carboline skeleton caused a marked decrease in binding to the benzodiazepine receptor. This observation supports the hypothesis that maximum binding affinity of beta-carbolines is achieved when the carbonyl group at position 3 is attached directly to the aromatic pyridine ring.

  DOI：

  10.1021/jm00371a002