2-(2-nitro-4-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline | 114688-64-1

• 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-(2-nitro-4-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-[(4-chloro-2-nitrophenyl)methyl]-3,4-dihydro-1H-isoquinoline
• CAS: 114688-64-1
• 化学式: C₁₆H₁₅ClN₂O₂
• 分子量: 302.76
• InChiKey: TZZQQIBLMWGORS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-nitro-4-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 生成 2-(2-amino-4-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline
  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-(2-nitro-4-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline
  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

文献信息

• KANMACHER, ISABELLE;STAMBACH, JEAN-FRANCOIS;JUNG, LOUIS;SCHOTT, CHRISTA;S+
  作者：KANMACHER, ISABELLE、STAMBACH, JEAN-FRANCOIS、JUNG, LOUIS、SCHOTT, CHRISTA、S+

  DOI：——

  日期：——
• US4925943A
  申请人：——

  公开号：US4925943A

  公开（公告）日：1990-05-15