2-氨基-4-乙基-5-氧代-4H,5h-吡喃o[3,2-c]色烯-3-甲腈 | 499785-45-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 2-氨基-4-乙基-5-氧代-4H,5h-吡喃o[3,2-c]色烯-3-甲腈
• 英文名称: 2-amino-4-ethyl-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
• 英文别名: 2-amino-4-ethyl-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-ethyl-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 499785-45-4
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: ASICXOLEJDTBNO-UHFFFAOYSA-N

物化性质

• 熔点：
  233 °C
• 溶解度：
  8.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22

反应信息

• 作为反应物：
  描述：

  2-氨基-4-乙基-5-氧代-4H,5h-吡喃o[3,2-c]色烯-3-甲腈 、 环己酮 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以93%的产率得到8-amino-7-ethyl-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
• 作为产物：
  描述：

  4-羟基香豆素 、 2-亚丙基丙二腈 在 (2-aminomethyl)phenol moiety on the surface of hydroxyapatite encapsulated maghemite (γ-Fe₂O₃) 作用下， 以 水 为溶剂， 生成 2-氨基-4-乙基-5-氧代-4H,5h-吡喃o[3,2-c]色烯-3-甲腈
  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

• Mono- and Bis-2-amino-4H-pyrans: Alum Catalyzed Three- or Pseudo Five-Component Reaction of 4-Hydroxycoumarin, Malononitrile and Aldehydes
  作者：Ali Reza Karimi、Cyrus Eslami

  DOI：10.2174/157017811794697421

  日期：2011.2.1

  An efficient method for the three- or pseudo five-component synthesis of mono- and bis-2-amino-4H-pyrans in excellent yields using Alum (KAl(SO4)2.12H2O) as recyclable catalyst is described. The present methodology offers several advantages such as excellent yields, simple procedures, shorter reaction times, milder conditions and the catalysts exhibited remarkable reusable activity.

  描述了一种有效的方法，该方法使用明矾（KAl（SO4）2.12H2O）作为可循环催化剂，以优异的产率三价或假五组分合成单和双-2-氨基-4H-吡喃。本方法提供了许多优点，例如优异的产率，简单的方法，较短的反应时间，较温和的条件以及催化剂显示出显着的可重复使用的活性。
• Another application of (NH₄)₄₂[Mo^VI₇₂Mo^V₆₀O₃₇₂(CH₃COO)₃₀(H₂O)₇₂] as a highly efficient recyclable catalyst for the synthesis of dihydropyrano[3,2-<i>c</i>]chromenes
  作者：Marziyeh Rohaniyan、Abolghasem Davoodnia、Ahmad Nakhaei

  DOI：10.1002/aoc.3479

  日期：2016.8

  catalyst for the synthesis of heterocyclic compounds, in this paper, we report another application of this attractive catalyst in the synthesis of 2‐amino‐5‐oxo‐4,5‐dihydropyrano[3,2‐c]chromene‐3‐carbonitriles via a one‐pot three‐component reaction of 4‐hydroxycoumarin, aldehydes and malononitrile. The reactions occur in ethanol–water as solvent at room temperature and the process is operative with

  在我们先前关于（NH 4）42 [Mo VI 72 Mo V 60 O 372（CH 3 COO）30（H 2 O）72 ]的应用的继续研究中，一种Keplerate型巨球纳米多孔异聚氧钼酸盐作为杂环化合物合成的催化剂，在本文中，我们报告了这种有吸引力的催化剂在2-氨基-5-氧代-4-4，5-二氢吡喃[3,2- c通过4-羟基香豆素，醛和丙二腈的一锅三组分反应生成] 3-亚甲基苯腈。该反应在室温下以乙醇-水为溶剂发生，并且该过程可与各种醛一起操作，从而以高收率得到相应的产物。该方案的其他有益特性包括反应时间短，后处理简单，催化剂的可回收性和可重复使用性（最多可连续运行五次）。版权所有©2016 John Wiley＆Sons，Ltd.
• 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.