3-乙酰基-4-羟基喹啉-2(1h)-酮 | 26138-64-7

• 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
• 中文名称: 3-乙酰基-4-羟基喹啉-2(1h)-酮
• 英文名称: 4-hydroxy-3-acetyl-1H-quinoline-2-one
• 英文别名: 3-acetyl-4-hydroxyquinolin-2(1H)-one；3-Acetyl-4-hydroxycarbostyril；3-acetyl-4-hydroxy-2(1H)-quinolinone；3-Acetyl-4-hydroxy-2-quinolone；3-acetyl-4-hydroxy-1H-quinolin-2-one
• CAS: 26138-64-7
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: UTOJPZBVJLHYGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  3-乙酰基-4-羟基喹啉-2(1h)-酮 在 sodium acetate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 9.0h， 以75%的产率得到(Z)-3-(1-hydrazonoethyl)-4-hydroxyquinoline-2(1H)-one
  参考文献：
  名称：

  Synthesis, antioxidant and toxicological study of novel pyrimido quinoline derivatives from 4-hydroxy-3-acyl quinolin-2-one

  摘要：

  A series of novel pyrimido and other fused quinoline derivatives like 4-methyl pyrimido [5,4-c]quinoline-2,5(1H,6H)-dione (4a), 4-methyl-2-thioxo-1,2-dihydropyrimido [5,4-c]quinoline-5(6H)-one (4b), 2-amino-4-methyl-1,2-dihydropyrimido [5,4-c]quinolin-5(6H)-one (4c), 3-methylisoxazolo [4,5-c]quinolin-4(5H)-one (4d), 3-methyl-1H-pyrazolo [4,3-c]quinoline-4(5H)-one (5e), 5-methyl-1H-[1,2,4] triazepino [6,5-c]quinoline-2,6(3H,7H)-dione (5f), 5-methyl-2-thioxo-2,3-dihydro-1H-[1,2,4]triazepino [6,5-c]quinolin-6(7H)one (5g) were synthesized regioselectively from 4-hydroxy-3-acyl quinolin-2-one 3. They were screened for their in vitro antioxidant activities against radical scavenging capacity using DPPH, Trolox equivalent antioxidant capacity (TEAC), total antioxidant activity by FRAP, superoxide radical (O-2(degrees-)) scavenging activity, metal chelating activity and nitric oxide scavenging activity. Among the compounds screened, 4c and 5g exhibited significant antioxidant activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.018
• 作为产物：
  描述：

  ethyl [(2-ethoxycarbonylaminophenyl)hydroxymethylidene]acetoacetate 在 甲醇 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 5.0h， 以89%的产率得到3-乙酰基-4-羟基喹啉-2(1h)-酮
  参考文献：
  名称：

  Synthesis of 3-Substituted 4-Hydroxyquinolin-2-ones via C-Acylation Reactions of Active Methylene Compounds with Functionalized 3,1-Benzoxazin-4-ones

  摘要：

  DOI：

  10.3987/com-99-8508

文献信息

• Substituted quinolinones. 18. 3-Acetyl-4-methylthioquinolin-2(1H)-one as useful synthon intermediate for synthesis of some new quinolinones
  作者：Mohamed M. Hassan、Elham S. Othman、Mohamed Abass

  DOI：10.1007/s11164-012-0678-7

  日期：2013.3

  reactions with some binucleophiles, hydrazine, hydroxylamine, urea, thiourea, semicarbazide, and thiosemicarbazide, furnishing some known five, six, and seven heterocyclic annellated quinolines. All the new compounds have been characterized using different spectral and analytical tools.

  已经制备了3-乙酰基-4-甲基硫代喹啉-2（ 1H ）-一（ 3 ），并且描述了其对用不同试剂，稀硫酸，氢氧化钠水溶液和过氧化氢处理的反应性。化合物 3 与苄胺，苯甲醛，DMF-DMA， Vilsmeier - Haack 试剂，2-氯-3-甲酰基-吡啶并嘧啶酮和丙二腈的反应已在方便的条件下进行。化合物 3 与一些双亲核试剂，肼，羟胺，尿素，硫脲，氨基脲和硫代氨基脲发生杂环化反应，从而提供了一些已知的五，六和七杂环环化喹啉。所有新化合物都使用不同的光谱和分析工具进行了表征。
• Robust synthesis of linear and angular furoquinolines using Rap–Stoermer reaction
  作者：Devadoss Karthik Kumar、Rayappan Rajkumar、Subramaniam Parameswaran Rajendran

  DOI：10.1007/s10593-016-1885-8

  日期：2016.5

  Rap–Stoermer reaction by conventional as well as microwave method that furnished an enhanced yield. Initially, we synthesized linear furo[2,3-b]quinolines from 3-acetyl-6-chloro-4-phenyl-1H-quinolin-2-one and three different α-halocarbonyl compounds: chloroacetophenone, ethyl chloroacetate, and chloroacetamide. The scope of the methodology was further extended to the synthesis of angular furo[3,2-c]quinolines

  我们通过常规和微波方法通过Rap-Stoermer反应合成了新颖的线性和有角呋喃喹啉，提高了收率。最初，我们从3-乙酰基-6-氯-4-苯基-1H-喹啉-2-酮和三种不同的α-卤代羰基化合物：氯乙酰苯，氯乙酸乙酯和氯乙酰胺合成了线性呋喃[2,3- b ]喹啉。通过利用3-乙酰基-4-羟基-1-甲基-1 H-喹啉-2-酮和α-卤代羰基化合物，该方法的范围进一步扩展到角呋喃[3,2- c ]喹啉的合成。
• Substituted 1, 4-thiazepine and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20020010169A1

  公开（公告）日：2002-01-24

  The present invention is directed to substituted 1,4-thiazepine and analogs thereof, represented by the general Formula I: 1 wherein the dashed lines, A 1 , A 2 , A 3 , X 1 and R 1 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of capases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被一般式I表示的取代的1,4-噻吩和其类似物，其中虚线、A1、A2、A3、X1和R1在此处被定义。本发明还涉及发现具有式I的化合物是卡泊酶激活剂和凋亡诱导剂。因此，本发明的卡泊酶激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生细胞死亡，其中异常细胞的不受控制的生长和扩散。
• Reactions of 2-methyl-3,1-benzoxazin-4-one with active methylene compounds: a new route to 3-substituted 4-hydroxyquinolin-2(1H)-ones
  作者：Anastasia Detsi、Vassilios Bardakos、John Markopoulos、Olga Igglessi-Markopoulou

  DOI：10.1039/p19960002909

  日期：——

  A new route to 3-substituted 4-hydroxyquinolin-2(1H)-ones, compounds of great biological importance, is described. The C-acylation of active methylene compounds 2 with the 2-methyl-3,1-benzoxazin-4-one 1, under basic conditions, leads to the formation of the new products 3–10, which have been isolated and characterized. Cyclization of the above intermediates furnishes the 3-substituted 4-hydroxyquinolin-2(1H)-ones. Spectral data and physical characteristics for all compounds are reported.

  描述了一种合成生物学意义重大的3-取代4-羟基喹啉-2(1H)-酮的新路线。在碱性条件下，将活性甲烷基化合物2与2-甲基-3,1-苯并氧杂嗪-4-酮1进行C-酰化反应，可以生成新的产物3-10，这些产物已被分离和表征。上述中间体的环化反应生成3-取代4-羟基喹啉-2(1H)-酮。所有化合物的光谱数据和物理特性均已报告。
• Novel quinolinone–pyrazoline hybrids: synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity
  作者：Ioanna Kostopoulou、Antonia Diassakou、Eleni Kavetsou、Eftichia Kritsi、Panagiotis Zoumpoulakis、Eleni Pontiki、Dimitra Hadjipavlou-Litina、Anastasia Detsi

  DOI：10.1007/s11030-020-10045-x

  日期：2021.5

  pyrazoline analogues (9a-9o). All the synthesized analogues were in vitro evaluated in terms of their antioxidant and soybean lipoxygenase (LOX) inhibitory activity. Among all the pyrazoline derivatives, compounds 9b and 9m were found to possess the best combined activity, whereas 9b analogue exhibited the most potent LOX inhibitory activity, with IC50 value 10 μM. The in silico docking results revealed that

  本项目致力于研究几种喹啉酮-查尔酮和喹啉酮-吡唑啉杂化物的构效关系，以期发现有前景的抗氧化剂和抗炎剂。为了实现这一目标，通过羟醛缩合反应合成了四种生物活性杂化喹啉酮-查尔酮化合物（8a-8d），然后进行化学修饰，形成十五种新的吡唑啉类似物（9a-9o）。所有合成的类似物均在体外评估其抗氧化和大豆脂氧合酶（LOX）抑制活性。在所有吡唑啉衍生物中，化合物9b和9m被发现具有最佳的综合活性，而9b类似物表现出最强的LOX抑制活性，IC50值为10 μM。计算机对接结果显示，合成的吡唑啉类似物 9b 显示出较高的 AutoDock Vina 评分（- 10.3 kcal/mol），而所有测试的衍生物均表现出与酶的变构相互作用。

表征谱图