tert-butyl 1-(4-(4-(diethylamino)butoxy)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1609169-68-7

• 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: tert-butyl 1-(4-(4-(diethylamino)butoxy)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS: 1609169-68-7
• 化学式: C₃₁H₄₆N₂O₅
• 分子量: 526.717
• InChiKey: HSLFCBFYVWHTAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  60.47
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-(4-(4-(diethylamino)butoxy)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以84.3%的产率得到4-(4-((6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)phenoxy)-N,N-diethylbutan-1-amine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of benzylisoquinoline derivatives as multifunctional agents against Alzheimer’s disease

  摘要：

  A novel series of benzylisoquinoline derivatives were designed, synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). The screening results showed that most of the compounds significantly inhibited cholinesterases (ChEs), human cholinesterases (h-ChEs) and self-induced beta-amyloid (A beta) aggregation. In particular, compound 9k showed the strongest acetylcholinesterase (AChE) inhibitory activity, being 1000-fold and 3-fold more potent than its precursor benzylisoquinoline (10) and the positive control galanthamine, respectively. In addition, 9k was a moderately potent inhibitor for h-ChEs. Compared with precursor benzylisoquinoline (36.0% at 20 mu M), 9k (78.4% at 20 mu M) could further inhibit Ab aggregation. Moreover, 9k showed low cell toxicity in human SH-SY5Y neuroblastoma cells. Therefore, compound 9k might be a promising lead compound for AD treatment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.058
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 丁酮 为溶剂， 反应 102.0h， 生成 tert-butyl 1-(4-(4-(diethylamino)butoxy)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of benzylisoquinoline derivatives as multifunctional agents against Alzheimer’s disease

  摘要：

  A novel series of benzylisoquinoline derivatives were designed, synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). The screening results showed that most of the compounds significantly inhibited cholinesterases (ChEs), human cholinesterases (h-ChEs) and self-induced beta-amyloid (A beta) aggregation. In particular, compound 9k showed the strongest acetylcholinesterase (AChE) inhibitory activity, being 1000-fold and 3-fold more potent than its precursor benzylisoquinoline (10) and the positive control galanthamine, respectively. In addition, 9k was a moderately potent inhibitor for h-ChEs. Compared with precursor benzylisoquinoline (36.0% at 20 mu M), 9k (78.4% at 20 mu M) could further inhibit Ab aggregation. Moreover, 9k showed low cell toxicity in human SH-SY5Y neuroblastoma cells. Therefore, compound 9k might be a promising lead compound for AD treatment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.058