2-amino-4-(3-methoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile | 156835-50-6

• 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-methoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
• CAS: 156835-50-6
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: KQLSQMRGOAUAOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  81.2
• 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-methoxyphenyl)-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-methoxyphenyl)-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 、 3-甲氧基苯甲醛 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以87%的产率得到2-amino-4-(3-methoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
  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

• Pyranoquinoline derivatives as inhibitors of cell proliferation
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0599514A2

  公开（公告）日：1994-06-01

  Pharmaceutical compounds of the formula R¹ is phenyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl and heteroaryl groups being optionally substituted, or R¹ is furanyl optionally substituted with C₁₋₄ alkyl; R² is nitrile, carboxy, -COOR⁴ where R⁴ is an ester group, -CONR⁵R⁶ where R⁵ and R⁶ are each hydrogen or C₁₋₄ alkyl, or R⁷SO₂- where R⁷ is C₁₋₄ alkyl or optionally substituted phenyl; R³ is -NR⁸R⁹, -NHCOR⁸, -N(COR⁸)₂, -N=CHOR⁸ where R⁸ and R⁹ are each hydrogen or C₁₋₄ alkyl, or -NHSO₂R¹⁰ where R¹⁰ is C₁₋₄ alkyl or optionally substituted phenyl; or where X is C₂₋₄ alkylene; and the group represents a pyridine ring fused to the benzopyran nucleus; and salts thereof.

  式中的药物化合物 R¹ 是苯基或选自噻吩基、吡啶基、苯并噻吩基、喹啉基、苯并呋喃基或苯并咪唑基的杂芳基，所述苯基和杂芳基可选择被取代，或者 R¹ 是可选择被 C₁₋₄ 烷基取代的呋喃基； R² 是腈、羧基、-COOR⁴（其中 R⁴ 是酯基）、-CONR⁵R⁶（其中 R⁵ 和 R⁶ 各为氢或 C₁₋₄ 烷基）或 R⁷SO₂- （其中 R⁷ 是 C₁₋₄ 烷基或任选取代的苯基）； R³ 是-NR⁸R⁹、-NHCOR⁸、-N(COR⁸)₂、-N=CHOR⁸（其中 R⁸ 和 R𠞙 分别是氢或 C₁₋₄ 烷基）或-NHSO₂R¹⁰（其中 R¹⁰ 是 C₁₋₄ 烷基或任选取代的苯基）；或 其中 X 是 C₂₋₄ 亚烷基；以及 基团 代表与苯并吡喃核融合的吡啶环； 及其盐类。
• US5434160A
  申请人：——

  公开号：US5434160A

  公开（公告）日：1995-07-18