2-[(4-chloro-2-nitrophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline | 152436-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-[(4-chloro-2-nitrophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
• CAS: 152436-72-1
• 化学式: C₁₈H₁₉ClN₂O₄
• 分子量: 362.813
• InChiKey: RDGLPXMOJIWQRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(4-chloro-2-nitrophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 生成 5-Chloro-2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-phenylamine
  参考文献：
  名称：

  2-(Aminobenzyl)-1,2,3,4-tetrahydroisoquinolines: a new class of α2-adrenergic receptor antagonists

  摘要：

  A new class of alpha2-adrenergic receptor antagonists, the 2-(aminobenzyl)-1,2,3,4-tetrahydroisoquinolines 4 and their derivatives, is described. Two synthetic routes are reported. An investigation of the structure-activity relationships including various substitutions of the isoquinoline moiety and the benzyl group is discussed. The affinity and selectivity for both alpha1- and alpha2-adrenoceptors was defined by studying the displacement of [H-3]-prazosin (alpha1-sites) and [H-3]-yohimbine (alpha2-sites) from rat brain membranes. The 2-(2-amino-3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 4a presented affinity and selectivity close to yohimbine. In functional experiments the alpha-adrenoceptor blocking properties of 4a have been evaluated on isolated rat aorta and on the twitch responses of the isolated rat vas deferens.

  DOI：

  10.1016/0223-5234(93)90130-7
• 作为产物：
  描述：

  4-氯-2-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 三乙胺 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 9.0h， 生成 2-[(4-chloro-2-nitrophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  2-(Aminobenzyl)-1,2,3,4-tetrahydroisoquinolines: a new class of α2-adrenergic receptor antagonists

  摘要：

  A new class of alpha2-adrenergic receptor antagonists, the 2-(aminobenzyl)-1,2,3,4-tetrahydroisoquinolines 4 and their derivatives, is described. Two synthetic routes are reported. An investigation of the structure-activity relationships including various substitutions of the isoquinoline moiety and the benzyl group is discussed. The affinity and selectivity for both alpha1- and alpha2-adrenoceptors was defined by studying the displacement of [H-3]-prazosin (alpha1-sites) and [H-3]-yohimbine (alpha2-sites) from rat brain membranes. The 2-(2-amino-3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 4a presented affinity and selectivity close to yohimbine. In functional experiments the alpha-adrenoceptor blocking properties of 4a have been evaluated on isolated rat aorta and on the twitch responses of the isolated rat vas deferens.

  DOI：

  10.1016/0223-5234(93)90130-7