2-amino-4-(3-fluorophenyl)-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-(3-fluorophenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
• 化学式: C₁₉H₁₂FN₃O
• 分子量: 317.322
• InChiKey: LGGZDGVQIFXHFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3-fluorophenyl)-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93%的产率得到7-(3-fluorophenyl)-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 、 丙二腈 、 3-氟苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-amino-4-(3-fluorophenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
  参考文献：
  名称：

  新的吡喃喹啉衍生物可破坏血管

  摘要：

  制备了一系列新的4-芳基-吡喃喹啉衍生物，重点是间硝基和间卤代苯基衍生物，并研究了它们对六种人类癌细胞系的结构依赖性抗增殖作用。这些化合物具有纳摩尔IC 50值的高活性。其中一些甚至在体外不影响已知的类似物如LY290181的活性，同时不影响非恶性成纤维细胞。这些活性最高的衍生物通过抑制微管蛋白聚合，导致癌细胞中活性氧的增加，并破坏了其微管细胞骨架。通过绒膜尿囊膜分析评估，他们还显示了卵内的血管破坏活性。

  DOI：

  10.1007/s00044-019-02406-5

文献信息

• New pyranoquinoline derivatives as vascular-disrupting anticancer agents
  作者：Florian Schmitt、Rainer Schobert、Bernhard Biersack

  DOI：10.1007/s00044-019-02406-5

  日期：2019.10

  A series of new 4-aryl-pyranoquinoline derivatives with a focus on meta-nitro and meta-halophenyl derivatives were prepared and investigated for their structure-dependent antiproliferative effects on a panel of six human cancer cell lines. The compounds were highly active with nanomolar IC50 values. Some of them even exceeded the activities of known analogs such as LY290181 in vitro while not affecting

  制备了一系列新的4-芳基-吡喃喹啉衍生物，重点是间硝基和间卤代苯基衍生物，并研究了它们对六种人类癌细胞系的结构依赖性抗增殖作用。这些化合物具有纳摩尔IC 50值的高活性。其中一些甚至在体外不影响已知的类似物如LY290181的活性，同时不影响非恶性成纤维细胞。这些活性最高的衍生物通过抑制微管蛋白聚合，导致癌细胞中活性氧的增加，并破坏了其微管细胞骨架。通过绒膜尿囊膜分析评估，他们还显示了卵内的血管破坏活性。
• 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.