3-acetyl-1-ethyl-4-hydroxy-2(1Η)-quinolinone | 161185-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-acetyl-1-ethyl-4-hydroxy-2(1Η)-quinolinone
• 英文别名: 3-acetyl-1-benzyl-4-hydroxy-2(1H)-quinolinone；3-acetyl-1-benzyl-4-hydroxyquinolin-2-one
• CAS: 161185-40-6
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: YTZYNMVQGCZKCI-UHFFFAOYSA-N

物化性质

• 沸点：
  480.9±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)
• 溶解度：
  11.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-羟基苯亚甲基丙二腈 、 3-acetyl-1-ethyl-4-hydroxy-2(1Η)-quinolinone 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以65%的产率得到5,7-diamino-2-(1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-4-(4-hydroxyphenyl)-4H-pyrano[2,3-b]pyridine-6-carbonitrile
  参考文献：
  名称：

  喹啉的研究：合成4 H，5 H，6 H，9 H-苯并[ ij ]吡喃并[2,3 - b ]喹啉-8-one，4 H-吡喃并[2,3 - b ]吡啶的新途径，2 H-吡喃-2-酮和吡喃并吡啶喹啉衍生物

  摘要：

  几种新的苯并[ IJ ]吡喃并[2,3- b ]喹嗪-8-酮5和4 ħ吡喃并[2,3- b ]吡啶8个衍生物由4-羟基喹啉的合成1。3-乙酰基-4-羟基-1-苯基-1 H-喹啉-2-一与二甲基甲酰胺二甲基缩醛反应，得到3-（3-二甲基亚氨基-丙烯酰基）-4-羟基-1-苯基-1 H-喹啉-2-一9。该产物与马尿酸和3-氧代戊二酸二乙酯反应，分别得到2 H-吡喃-2-酮13和吡喃并吡啶喹啉17。

  DOI：

  10.1002/jhet.5570420529
• 作为产物：
  描述：

  6-Benzyl-4-hydroxy-6H-pyrano[3,2-c]quinoline-2,5-dione 在 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 1.5h， 以92%的产率得到3-acetyl-1-ethyl-4-hydroxy-2(1Η)-quinolinone
  参考文献：
  名称：

  Syntheses of 3-Acyl-4-hydroxy-2(1H)quinolones

  摘要：

  3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyrano[3,2-c]quinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3. Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)quinolones 8. Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.

  DOI：

  10.1002/prac.19943360707

文献信息

• Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series
  作者：Marina Roussaki、Belinda Hall、Sofia Costa Lima、Anabela Cordeiro da Silva、Shane Wilkinson、Anastasia Detsi

  DOI：10.1016/j.bmcl.2013.09.047

  日期：2013.12

  A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3 +/- 0.1 mu M). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1 +/- 0.6 and 3.1 +/- 1.05 mu M, respectively). Promising trypanocidal compounds include 5 and 10 (IC50 values of 2.6 +/- 0.1 and 3.3 +/- 0.1 mu M, respectively) as well as 6 and 9 (both having IC50 values of <5 mu M). Chemical modifications on the quinolinone-chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity. (C) 2013 Elsevier Ltd. All rights reserved.