1,3-bis((8-isopropylisoquinolin-1-yl)methyl)benzene | 1346707-58-1

• 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: 1,3-bis((8-isopropylisoquinolin-1-yl)methyl)benzene
• 英文别名: 1,1'-(m-xylyl)-bis-(8-isopropyl-isoquinoline)
• CAS: 1346707-58-1
• 化学式: C₃₂H₃₂N₂
• 分子量: 444.619
• InChiKey: SBBOLCBYVXSKFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,3-bis((8-isopropylisoquinolin-1-yl)methyl)benzene 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到1,1'-(1,3-phenylenebis(methylene))bis(8-isopropyl-2-methylisoquinolinium) iodide
  参考文献：
  名称：

  Synthesis and radioligand binding studies of bis-(8-isopropyl-isoquinolinium) derivatives as ligands for apamin-sensitive sites on cloned SK2 and SK3 channels

  摘要：

  A structure-activity relationship study of N-methyl-laudanosine, a SK channel blocker, has indicated that the 6,7-dimethoxy group could be successfully replaced by a hydrophobic moiety such as an isopropyl substituent in position 8 of the isoquinoline ring. In the present study, bis-(8-isopropyl-isoquinolinium) derivatives (2a-e) were synthesized and tested for their affinity for cloned SK2 and SK3 channels in comparison with their 6,7-dimethoxy analogues (4a-f). Several ligands were investigated, both in flexible (propyl, butyl and pentyl) and rigid (m-or p-xylyl) series, the m-xylyl derivative (2d) having the best profile in terms of affinity and selectivity for SK3/SK2 channels. Molecular studies showed that the optimal conformation of compound 2d fits well with our SK pharmacophore model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.043
• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 1,3-bis((8-isopropylisoquinolin-1-yl)methyl)benzene
  参考文献：
  名称：

  Synthesis and radioligand binding studies of bis-(8-isopropyl-isoquinolinium) derivatives as ligands for apamin-sensitive sites on cloned SK2 and SK3 channels

  摘要：

  A structure-activity relationship study of N-methyl-laudanosine, a SK channel blocker, has indicated that the 6,7-dimethoxy group could be successfully replaced by a hydrophobic moiety such as an isopropyl substituent in position 8 of the isoquinoline ring. In the present study, bis-(8-isopropyl-isoquinolinium) derivatives (2a-e) were synthesized and tested for their affinity for cloned SK2 and SK3 channels in comparison with their 6,7-dimethoxy analogues (4a-f). Several ligands were investigated, both in flexible (propyl, butyl and pentyl) and rigid (m-or p-xylyl) series, the m-xylyl derivative (2d) having the best profile in terms of affinity and selectivity for SK3/SK2 channels. Molecular studies showed that the optimal conformation of compound 2d fits well with our SK pharmacophore model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.043