2-amino-4-(p-methoxyphenyl)-4H-pyrano<3,2-h>quinoline-3-carbonitrile | 119825-09-1

• 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-(p-methoxyphenyl)-4H-pyrano<3,2-h>quinoline-3-carbonitrile
• 英文别名: 2-amino-4-(4'-methoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile；2-amino-4-(4-methoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile；2-amino-4-(p-methoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile
• CAS: 119825-09-1
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: NGMHEGLNXGMIRI-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  574.8±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

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：

  环己酮 、 2-amino-4-(p-methoxyphenyl)-4H-pyrano<3,2-h>quinoline-3-carbonitrile 在 aluminum (III) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以89%的产率得到7-(4-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 、 (4-甲氧基苄烯)丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以70%的产率得到2-amino-4-(p-methoxyphenyl)-4H-pyrano<3,2-h>quinoline-3-carbonitrile
  参考文献：
  名称：

  杂环合成中的腈。吡喃并[3,2-h]喹啉衍生物的合成与反应

  摘要：

  8-喹啉醇在碱性催化剂存在下与肉桂腈衍生物反应，得到吡喃并[3,2-h]喹啉（3a-f）。3a与乙酸酐/吡啶、甲酰胺、甲酸/甲酰胺和二硫化碳等试剂反应得到稠合杂四环系统嘧啶[4',5':6,5]吡喃并[3,2-h]喹啉。

  DOI：

  10.1246/bcsj.64.668

文献信息

• Ce–Zr/SiO2: a versatile reusable heterogeneous catalyst for three-component synthesis and solvent free oxidation of benzyl alcohol
  作者：Ramakanth Pagadala、Suresh Maddila、Surjyakanta Rana、Sreekantha B. Jonnalagadda

  DOI：10.1039/c3ra47145d

  日期：——

  Ce–Zr loaded on SiO2 as catalyst provides an extremely efficient method to synthesize pyranoquinolines. This catalyst is found to be superb for the three-component synthesis of target compounds and for the solvent-free liquid-phase oxidation of benzyl alcohols. The catalyst is fully recoverable and reusable with no loss of catalytic activity even after multiple cycles.

  负载在SiO 2上的Ce-Zr作为催化剂提供了一种合成吡喃喹啉的极其有效的方法。发现该催化剂对于目标化合物的三组分合成和苄醇的无溶剂液相氧化是极好的。该催化剂是完全可回收的并且可重复使用的，即使经过多个循环也不会损失催化活性。
• 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。
• Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines
  作者：Nimesh R. Kamdar、Dhaval D. Haveliwala、Prashant T. Mistry、Saurabh K. Patel

  DOI：10.1016/j.ejmech.2010.08.014

  日期：2010.11

  The clinical significance of pyran and pyrimidine condensed systems and the raise in problem of multidrug resistant bacterial pathogens has directed us to synthesize pyranopyrimidine derivatives via the reactions of the versatile, 2-amino-4-(4-methoxyphenyl)-4H-substitutedchromene-3-carbonitrile with the appropriate reagents. The newly synthesized compounds were characterized by IR, H-1 NMR,C-13 NMR, Mass spectra and Elemental analysis. The compounds were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H(37)Rv [ATCC-27294] and antibacterial activity against Staphylococcus aureus [ATCC-25923] and Streptococcus pyogenes [MTCC-443] as Gram-positive, Escherichia coli [ATCC-25922] and Pseudomonas aeruginosa [MTCC-441] as Gram-negative bacterial strains and antifungal activity against Aspergillus niger [MTCC-282]. Several derivatives exhibited pronounced antitubercular and antimicrobial activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Elagamey, Abdel Ghani A.; Sawllim, Salah Z.; El-Taweel, Fathy M.A., Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 7, p. 1534 - 1538
  作者：Elagamey, Abdel Ghani A.、Sawllim, Salah Z.、El-Taweel, Fathy M.A.、Elnagdi, Mohamed H.

  DOI：——

  日期：——
• Sarasija; Sudershan; Ashok, Indian Journal of Heterocyclic Chemistry, 2014, vol. 23, # 4, p. 377 - 380
  作者：Sarasija、Sudershan、Ashok、Shivaraj

  DOI：——

  日期：——