6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸甲酯盐酸盐 | 30740-96-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸甲酯盐酸盐
• 中文别名: 6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-甲酸甲酯盐酸盐
• 英文名称: methyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride
• 英文别名: 6,7-dimethoxy-3-carbomethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride；methyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate;hydrochloride
• CAS: 30740-96-6
• 化学式: C₁₃H₁₇NO₄*ClH
• 分子量: 287.743
• InChiKey: ZSBSOZGGWBVSAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  56.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  (E)-5-(2-carboxyvinyl)-2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid 、 6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸甲酯盐酸盐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-[(E)-3-[3-(6,7-dimethoxy-3-methoxycarbonyl-3,4-dihydro-1H-isoquinoline-2-carbonyl)-2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-3-carboxylate
  参考文献：
  名称：

  Derivatives of 8-epiblechnic Acid and their Effects on Down-Regulation of Endothelin (ETA) receptor mRNA

  摘要：

  本申请公开了8-epiblechnic酸的衍生物及其在治疗与内皮素受体A或内皮素-1（ET-1）过度表达相关的疾病中的应用，例如高血压，癌症，动脉粥样硬化和心肌梗死。

  公开号：

  US20100048618A1
• 作为产物：
  描述：

  2-硝基苯磺酰胺 在 盐酸 、 硫酸 作用下， 反应 96.0h， 生成 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

文献信息

• Biomimetic approach to potential benzodiazepine receptor agonists and antagonists
  作者：Filadelfo Guzman、Michael Cain、Paul Larscheid、Tim Hagen、James M. Cook、Margaret Schweri、Phil Skolnick、Steven M. Paul

  DOI：10.1021/jm00371a002

  日期：1984.5

  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.
• Derivatives of 8-epiblechnic Acid and their Effects on Down-Regulation of Endothelin (ETA) receptor mRNA
  申请人：Chan Hardy

  公开号：US20100048618A1

  公开（公告）日：2010-02-25

  The present application discloses derivatives of 8-epiblechnic acid and use thereof in treating a disease related to endothelin receptor A or endothelin-1 (ET-1) over-expression, such as hypertension, cancer, atherosclerosis, and myocardial infarction.

  本申请公开了8-epiblechnic酸的衍生物及其在治疗与内皮素受体A或内皮素-1（ET-1）过度表达相关的疾病中的应用，例如高血压，癌症，动脉粥样硬化和心肌梗死。