8-amino-7-(p-tolyl)-9,10,11,12-tetrahydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one | 1470027-73-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-amino-7-(p-tolyl)-9,10,11,12-tetrahydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one
• 英文别名: 15-Amino-13-(4-methylphenyl)-2,10-dioxa-22-azapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4,6,8,14,16(21)-heptaen-11-one；15-amino-13-(4-methylphenyl)-2,10-dioxa-22-azapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4,6,8,14,16(21)-heptaen-11-one
• CAS: 1470027-73-6
• 化学式: C₂₆H₂₂N₂O₃
• 分子量: 410.472
• InChiKey: WDXBVMSYHHZRAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 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：
  74.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-甲基亚苄基)-丙二腈 在 aluminum (III) chloride 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 8-amino-7-(p-tolyl)-9,10,11,12-tetrahydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one
  参考文献：
  名称：

  Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3′,4′:5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase

  摘要：

  Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50 = 5 nM). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.045

文献信息

• Efficient and Facile Synthesis of Chromenopyrano[2,3-b] pyridine Derivatives Catalyzed by Sodium Carbonate
  作者：Raziyeh Keshavarz、Mahnaz Farahi、Bahador Karami

  DOI：10.17344/acsi.2020.6266

  日期：——

  In this research, a number of new and known chromenopyrano[2,3-b]pyridine derivatives have been prepared. Initially, according to the reported procedure, pyrano[2,3-c]chromene derivatives were synthesized by the reaction between 4-hydroxycoumarin, aromatic aldehydes and malononitrile using silica sodium carbonate (SSC) as the catalyst. Next, the prepared pyrano[2,3-c]chromenes were reacted by dimethyl acetylenedicarboxylate (DMAD) or cyclohexanone in the presence of sodium carbonate to produce chromenopyrano[2,3-b]pyridine derivatives. The presented protocol avoids the use of expensive catalysts and gives useful potentially bioactive heterocycles in excellent to high yields.

  在这项研究中，制备了一系列新的和已知的咔啉并吡喃并[2,3-b]吡啶衍生物。首先，根据报道的程序，使用二氧化硅碳酸钠（SSC）作为催化剂，通过对4-羟基香豆素、芳香醛和丙二腈的反应合成了吡喃并[2,3-c]咔啉衍生物。接下来，制备的吡喃并[2,3-c]咔啉与二甲基乙炔二羧酸二甲酯（DMAD）或环己酮在碳酸钠存在下反应，生成了咔啉并吡喃并[2,3-b]吡啶衍生物。该方法避免了使用昂贵的催化剂，并以优良至高收率产生了有用的潜在生物活性杂环化合物。
• Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3′,4′:5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase
  作者：Mehdi Khoobi、Masoumeh Alipour、Alireza Moradi、Amirhossein Sakhteman、Hamid Nadri、Seyyede Faeze Razavi、Mehdi Ghandi、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2013.07.045

  日期：2013.10

  Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50 = 5 nM). (C) 2013 Elsevier Masson SAS. All rights reserved.