1-(2',4'-dichlorobenzyl)-6-chloro-7-hydroxy-N-methyl-1,2,3,4-tetrahydroisoquinoline | 1198132-28-3

• 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: 1-(2',4'-dichlorobenzyl)-6-chloro-7-hydroxy-N-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6-chloro-1-[(2,4-dichlorophenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
• CAS: 1198132-28-3
• 化学式: C₁₇H₁₆Cl₃NO
• 分子量: 356.679
• InChiKey: ANSPOQSLVFCMFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2',4'-dichlorobenzyl)-6-chloro-7-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline 在 三溴化硼 、 ammonium hydroxide 、 盐酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 以80%的产率得到1-(2',4'-dichlorobenzyl)-6-chloro-7-hydroxy-N-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives

  摘要：

  Two series of halogenated 1-benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines were prepared to explore the influence of each series on the affinity for dopamine receptors. All the compounds displayed a high affinity for D-1-like and/or D-2-like dopamine receptors in striatal membranes, although they were unable to inhibit [H-3]-dopamine uptake in striatal synaptosomes. The halogen placed on the benzylic ring in 1-benzyl-THIQs, compounds of the series 1, 2'-bromobenzyl derivatives with K-i values into the nanomolar range, and the series 2, 2',4'-dichlorobenzyl-THIQ homologues, proves to be an important factor to modulate affinity at dopamine receptor. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.033