2H,3H,6H,7H,8H,9H-[1,4]dioxino[2,3-g]isoquinoline hydrochloride | 1443981-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2H,3H,6H,7H,8H,9H-[1,4]dioxino[2,3-g]isoquinoline hydrochloride
• 英文别名: 2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline;hydrochloride
• CAS: 1443981-10-9
• 化学式: C₁₁H₁₃NO₂*ClH
• mdl: MFCD24842823
• 分子量: 227.691
• InChiKey: LRJZGBXWGFSKHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  30.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2H,3H,6H,7H,8H,9H-[1,4]dioxino[2,3-g]isoquinoline hydrochloride 在 lithium aluminium tetrahydride 、 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3,6,8,9-tetrahydro-2H-[1,4]dioxino[2,3-g]isoquinolin-7-yl)butan-1-amine
  参考文献：
  名称：

  Synthesis and in vitro evaluation of tetrahydroisoquinolinyl benzamides as ligands for σ receptors

  摘要：

  5-Bromo-N-[4-(6,7-diinethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2,3-dimethoxy-benzamide (1) is one of the most potent and selective sigma(2) receptor ligands reported to date. Previous structure-activity relationship studies of such tetrahydroisoquinolinyl benzamides have focused on the linker that connects the ring systems and the effects of benzamide ring substituents. The present study explores the effects of fusing methylene-, ethylene-, and propylenedioxy rings onto the tetrahydroisoquinoline in place of the two methoxy groups. These modifications decreased sigma(2) affinity by 8- to 12-fold, with no major differences noted with ring size. By contrast, the methylenedioxy analog showed a 10-fold greater sigma(1) affinity than 1, and progressively lower sigma(1) affinities were then noted with increasing ring size. We also opened the tetrahydroisoquinoline ring of 1 to study the effects of greater conformational fluidity on a receptor binding. The sigma(2) affinity of the open-ring compound decreased by 1700-fold, while a, affinity was not changed. Thus, a constrained tetrahydroisoquinoline ring system is key to the exceptional sigma(2) receptor binding affinity and selectivity of this active series. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.005
• 作为产物：
  描述：

  四氢-6,7-异喹啉二醇 在 盐酸 、 四丁基溴化铵 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 2H,3H,6H,7H,8H,9H-[1,4]dioxino[2,3-g]isoquinoline hydrochloride
  参考文献：
  名称：

  WO2019079519A5

  摘要：

  公开号：

  WO2019079519A5