7-(p-tolyl)-9,10,11,12-tetrahydro-7H-pyrano[2,3-b:5,6-h']diquinolin-8-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(p-tolyl)-9,10,11,12-tetrahydro-7H-pyrano[2,3-b:5,6-h']diquinolin-8-amine
• 英文别名: 13-(4-Methylphenyl)-2-oxa-5,22-diazapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4(9),5,7,10,14,16(21)-octaen-15-amine；13-(4-methylphenyl)-2-oxa-5,22-diazapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4(9),5,7,10,14,16(21)-octaen-15-amine
• 化学式: C₂₆H₂₃N₃O
• 分子量: 393.488
• InChiKey: QWBLOIWIJRGVSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 在 哌啶 、 aluminum (III) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.25h， 生成 7-(p-tolyl)-9,10,11,12-tetrahydro-7H-pyrano[2,3-b:5,6-h']diquinolin-8-amine
  参考文献：
  名称：

  Tetrahydropyranodiquinolin-8-amines as new, non hepatotoxic, antioxidant, and acetylcholinesterase inhibitors for Alzheimer's disease therapy

  摘要：

  Herein we report an efficient two step synthesis and biological assessment of 12 racemic tetrahydropyranodiquinolin-8-amines derivatives as antioxidant, cholinesterase inhibitors and non-hepatotoxic agents. Based on the results of the primary screening, we identified 7-(3-methoxypheny1)-9,10,11,12-tetrahydro-7H-pyrano[2,3-b:5,6-h']diquinolin-8-amine (2h) as a particularly interesting nonhepatotoxic compound that shows moderate antioxidant activity (1.83 equiv Trolox in the ORAC assay), a non competitive inhibition of hAChE (IC50 = 0.75 +/- 0.01 mu M), and brain permeable as determined by the PAMPA-Blood Brain Barrier assay. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.050

文献信息

• Tetrahydropyranodiquinolin-8-amines as new, non hepatotoxic, antioxidant, and acetylcholinesterase inhibitors for Alzheimer's disease therapy
  作者：Youssef Dgachi、Olga Sokolov、Vincent Luzet、Justyna Godyń、Dawid Panek、Alexandre Bonet、Hélène Martin、Isabel Iriepa、Ignacio Moraleda、Cristina García-Iriepa、Jana Janockova、Lysiane Richert、Ondrej Soukup、Barbara Malawska、Fakher Chabchoub、José Marco-Contelles、Lhassane Ismaili

  DOI：10.1016/j.ejmech.2016.11.050

  日期：2017.1

  Herein we report an efficient two step synthesis and biological assessment of 12 racemic tetrahydropyranodiquinolin-8-amines derivatives as antioxidant, cholinesterase inhibitors and non-hepatotoxic agents. Based on the results of the primary screening, we identified 7-(3-methoxypheny1)-9,10,11,12-tetrahydro-7H-pyrano[2,3-b:5,6-h']diquinolin-8-amine (2h) as a particularly interesting nonhepatotoxic compound that shows moderate antioxidant activity (1.83 equiv Trolox in the ORAC assay), a non competitive inhibition of hAChE (IC50 = 0.75 +/- 0.01 mu M), and brain permeable as determined by the PAMPA-Blood Brain Barrier assay. (C) 2016 Elsevier Masson SAS. All rights reserved.