2-amino-4-(4'-methylphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-amino-4-(4'-methylphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
• 英文别名: 2-amino-4-(p-tolyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile；4H-Pyrano[3,2-H]quinoline-3-carbonitrile, 2-amino-4-(4-methylphenyl)-；2-amino-4-(4-methylphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
• 化学式: C₂₀H₁₅N₃O
• 分子量: 313.359
• InChiKey: ZWSCNYBAYYLQHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(4'-methylphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile 、 环己酮 在 aluminum (III) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以90%的产率得到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
• 作为产物：
  描述：

  8-羟基喹啉 、 对甲基苯甲醛 、 丙二腈 在 indium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 0.12h， 以88%的产率得到2-amino-4-(4'-methylphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
  参考文献：
  名称：

  InCl3促进微波辐射合成吡喃并[3,2-h]喹啉

  摘要：

  有效和经济的方法已被开发用于吡喃并[3,2的合成ħ〕喹啉通过三氯化铟催化一锅三组分8-羟基喹啉的用微波照射下芳香醛和丙二腈/氰基乙酸乙酯反应。

  DOI：

  10.1002/jhet.2067

文献信息

• InCl₃Promoted Synthesis of Pyrano[3,2-<i>h</i>]quinolines via Microwave Irradiation
  作者：Gopal Senthil Kumar、Matthias Zeller、Michael A. Frasso、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1002/jhet.2067

  日期：2015.5

  An efficient and economical method has been developed for the synthesis of pyrano[3,2‐h]quinolines via an indium trichloride‐catalyzed one‐pot three‐component reaction of 8‐hydroxyquinoline with aromatic aldehydes and malononitrile/ethyl cyanoacetate under microwave irradiation.

  有效和经济的方法已被开发用于吡喃并[3,2的合成ħ〕喹啉通过三氯化铟催化一锅三组分8-羟基喹啉的用微波照射下芳香醛和丙二腈/氰基乙酸乙酯反应。
• Sarasija; Sudershan; Ashok, Indian Journal of Heterocyclic Chemistry, 2014, vol. 23, # 4, p. 377 - 380
  作者：Sarasija、Sudershan、Ashok、Shivaraj

  DOI：——

  日期：——
• 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.
• Novel 4-Aryl-4H-chromene derivative displayed excellent in vivo anti-glioblastoma efficacy as the microtubule-targeting agent
  作者：Haoyi Yang、Dongyu Zhang、Ziyang Yuan、Haishi Qiao、Zhuolu Xia、Feng Cao、Yuanyuan Lu、Feng Jiang

  DOI：10.1016/j.ejmech.2024.116205

  日期：2024.3