8-amino-7-(3,4-dimethoxyphenyl)-9,10,11,12-tetrahydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one | 1470027-75-8

• 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-(3,4-dimethoxyphenyl)-9,10,11,12-tetrahydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one
• 英文别名: 15-Amino-13-(3,4-dimethoxyphenyl)-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-(3,4-dimethoxyphenyl)-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: 1470027-75-8
• 化学式: C₂₇H₂₄N₂O₅
• 分子量: 456.498
• InChiKey: VDZUTMLPMJJFJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ((3,4-二甲氧基苯基)亚甲基)甲烷-1,1-二甲腈 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-(3,4-dimethoxyphenyl)-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