7-acetoxy-4-methylquinolin-2-one | 354130-49-7

• 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
• 英文名称: 7-acetoxy-4-methylquinolin-2-one
• 英文别名: 7-acetoxy-4-methylquinoline-2-one；7-acetoxy-4-methyl-2-oxo-1H-quinoline；4-methyl-2-oxo-1,2-dihydroquinolin-7-yl acetate；7-acetoxy-4-methylquinolone；(4-methyl-2-oxo-1H-quinolin-7-yl) acetate
• CAS: 354130-49-7
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: MJUQZIOCDRSGDY-UHFFFAOYSA-N

物化性质

• 熔点：
  257-258 °C(Solv: ethanol (64-17-5))
• 沸点：
  405.0±45.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-acetoxy-4-methylquinolin-2-one 在 三氯化铝 作用下， 反应 4.0h， 以68%的产率得到6-acetyl-7-hydroxy-4-methylquinolin-2-one
  参考文献：
  名称：

  呋喃喹啉衍生物的新合成

  摘要：

  7-acyloxyquinolin-2-one 和 7-acyloxy-2-chloroquinoline 衍生物及其类似物的 Fries 重排为呋喃喹啉衍生物合成的新途径提供了有用的中间体。介绍 首先，已知呋喃香豆素、补骨脂素和当归衍生物具有很高的光生物活性。然而，它们也表现出一些负面的副作用。例如，紫外光下呋喃香豆素的高活性提供了 DNA 交联，从而可能导致癌症疾病。已经发现，内酯环中除氧原子外还含有其他杂原子的呋喃香豆素类似物没有这些副作用。因此，呋喃喹啉衍生物（尤其是呋喃喹啉-2-one 衍生物）作为呋喃香豆素类似物备受关注。文献中有一些呋喃喹啉-2-一衍生物合成 5 ' 6 的方案。在研究呋喃香豆素杂类似物制备的新方法时，我们发现乙酰氧基喹啉衍生物的 Fries 重排是获得最终呋喃喹啉的关键中间体的有用反应。我们早先已经成功地在许多呋喃香豆素的合成中使用了 Fries 重排。例如，用过量的氯化铝处理

  DOI：

  10.1515/hc.2004.10.4-5.273
• 作为产物：
  描述：

  1-氨基-7-羟基-4-甲基喹啉-2-酮 在 Glyoxylsaeure-ethylester-thiosemicarbazon 、 溶剂黄146 作用下， 反应 6.0h， 生成 7-acetoxy-4-methylquinolin-2-one
  参考文献：
  名称：

  Synthesis of Some Hybrid 7-Hydroxy Quinolinone Derivatives As Anti Breast Cancer Drugs

  摘要：

  研究人员合成了一系列新的 2-喹啉酮混合衍生物，并利用光谱和元素分析数据证明了其结构。所有制备的化合物都对 MCF-7 细胞系进行了体外细胞毒性活性测试。化合物 6 和 8 显示出了强大的抗癌活性，与参考化合物多柔比星相当。化合物 3 的抗癌活性与顺铂相当。化合物 6 和 8 的细胞周期分析表明，细胞周期停滞在 S 期和 G2/M 期，并在前 G1 期诱导细胞凋亡。DNA 合成抑制活性表明，化合物 6 的活性与多柔比星相当。细胞凋亡的程度也是通过 Annexin V-FITC 检测法确定的。此外，与未处理的对照组相比，化合物 6 和 8 使效应 Caspase 3 的活化增加了四倍。另一方面，化合物 3、6 和 8 在细胞核中定位。

  DOI：

  10.1007/s11164-019-03827-y

文献信息

• [EN] COUMARIN COMPOUNDS FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS<br/>[FR] COMPOSÉS DE COUMARINE POUR LE TRAITEMENT D'INFECTIONS MYCOBACTÉRIENNES
  申请人：UNIV DELHI

  公开号：WO2012137224A1

  公开（公告）日：2012-10-11

  The present invention relates to method for treating mycobacterial infection/disease by administration of a therapeutically effective amount of compound of formula I.

  本发明涉及通过给予化合物I的治疗有效量来治疗分枝杆菌感染/疾病的方法。
• Synthesis, photooxygenation, and characterization of new angular furoquinolinone derivatives, a new furocoumarin bioisoster
  作者：Sameh Elgogary、Hoda Abd Elghafar、Mohammad Mashaly

  DOI：10.1002/jccs.202000455

  日期：——

  via Williamson reaction of hydroxyquinolinones with α-haloketones, such as 3-chloro-2-butanone and phenacyl bromide, followed by treatment with polyphosphoric acid (PPA). The synthesized angular furoquinolinones were photooxygenated in chloroform or dimethyl formamide and in the presence of tetraphenylporphyrin (TPP) as a singlet oxygen sensitizer (1O2). The photooxygenation reactions furnished the

  通过羟基喹啉酮与α-卤代酮（如3-氯-2-丁酮和苯甲酰溴）的威廉姆森反应，然后用多磷酸（PPA）处理，合成了具有新骨架结构的角状呋喃喹啉酮衍生物。合成的角状呋喃喹啉酮在氯仿或二甲基甲酰胺中进行光氧化，并在四苯基卟啉 (TPP) 作为单线态氧敏化剂 ( 1 O 2 )存在下进行光氧化。光氧化反应通过[2+2]环加成反应提供光裂解产物。所有光产品都被分离出来并通过光谱分析进行了充分表征。
• Synthesis of some benzo[c][2,6]naphthyridin-5-ones and new tetracyclic benzofuro[4,5-c]-2,6-naphthyridin-5(6H)-ones
  作者：Adriana Chilin、Paolo Manzini、Alessia Confente、Giovanni Pastorini、Adriano Guiotto

  DOI：10.1016/s0040-4020(02)01325-x

  日期：2002.12

  methylbenzofuro[4,5-c]-2,6-naphthyridin-5(6H)-ones were synthesized, first building the pyridine nucleus on the appropriated quinolin-2-ones, and then condensing the furan ring on the preconstituted benzonaphthyridinones. The benzo[c][2,6]naphthyridinic nucleus was also interesting for its known pharmacological properties, as well as intermediate for the synthesis of natural product analogues.

  合成了一系列新颖的甲基苯并呋喃[4,5 - c ] -2,6-萘啶-5（6 H）-one，首先在合适的喹啉-2-ones上构建吡啶核，然后将呋喃环缩合在预制的苯并萘啶酮。苯并[ c ] [2,6]萘啶核也因其已知的药理特性以及用于合成天然产物类似物的中间体而引起人们的兴趣。
• Synthesis and biological evaluation of some hybrid 2-quinolinone derivatives containing cinnamic acid as anti-breast cancer drugs
  作者：S. B. Bakare

  DOI：10.4314/bcse.v35i3.7

  日期：——

  ABSTRACT. A new series of hybrid 2-quinolinone derivatives were synthesized by using 7-hydroxy-4-methyl-1-amino-quinolin-2-one (2) and cinnamic acid. Hybrid halogenated 2-quinolinone derivatives (3-(7-hydroxy-4-methyl-3,6,8-tribromo-2-oxo-2H-quinolin-1-ylamino)-3-phenyl acrylic acid (4) and 3-(7-acetoxy-4-methyl-3,6,8-tribromo-2-oxo-1H-quinolin-1-ylamino)-3-phenyl acrylic acid (7)) were prepared via the halogenation of 3-(7-hydroxy-4-methyl-2-oxo-2H-quinolin-1-ylamino)-3-phenyl acrylic acid (3) with bromine to give compound 4 with acetic anhydride led to the formation of hydride halogenated 2-quinolinone derivative (7). All the synthesized hybrid 2-quinolinone and hybrid halogenated 2-quinolinone derivatives were tested for their cytotoxicity against MCF-7 cell line. DNA flow cytometric analysis of compounds 3 showed cell cycle arrest at G2/M phase with concomitant increase of cells in apoptotic phase. Dual annexin-V/propidium iodide staining assay of compound 3 revealed that, the selected molecule increases the apoptosis of MCF-7 cells more than control.                     KEY WORDS: Quinolinone, Hybrid, Cinnamic acid, Apoptosis, MCF-7 cells   Bull. Chem. Soc. Ethiop. 2021, 35(3), 551-564. DOI: https://dx.doi.org/10.4314/bcse.v35i3.7

  摘要：通过使用7-羟基-4-甲基-1-氨基-喹啉-2-酮（2）和肉桂酸，合成了一系列新的杂化2-喹啉酮衍生物。通过卤代反应制备了杂化卤代2-喹啉酮衍生物（3-（7-羟基-4-甲基-3,6,8-三溴-2-氧代-2H-喹啉-1-基氨基）-3-苯基丙烯酸（4）和3-（7-乙酰氧基-4-甲基-3,6,8-三溴-2-氧代-1H-喹啉-1-基氨基）-3-苯基丙烯酸（7））。将3-（7-羟基-4-甲基-2-氧代-2H-喹啉-1-基氨基）-3-苯基丙烯酸（3）卤代反应制备化合物4，使用乙酸酐导致卤代氢化2-喹啉酮衍生物（7）的形成。测试了所有合成的杂化2-喹啉酮和杂化卤代2-喹啉酮衍生物对MCF-7细胞系的细胞毒性。化合物3的DNA流式细胞术分析显示细胞周期在G2/M期停滞，并伴随着细胞凋亡期的增加。化合物3的双重annexin-V/丙啶碘染色实验表明，所选的分子增加了MCF-7细胞的凋亡程度，比对照组更高。 关键词：喹啉酮，杂化，肉桂酸，细胞凋亡，MCF-7细胞 《埃塞俄比亚化学学会会报》2021年第35卷第3期，551-564页。DOI：https://dx.doi.org/10.4314/bcse.v35i3.7
• Characterization of 4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate as an effective antiplatelet agent
  作者：Nivedita Priya、Anjali Gupta、Karam Chand、Prabhjot Singh、Abha Kathuria、Hanumantharao G. Raj、Virinder S. Parmar、Sunil K. Sharma

  DOI：10.1016/j.bmc.2010.04.011

  日期：2010.6.1

  We have studied earlier a membrane bound novel enzyme Acetoxy Drug: protein transacetylase identified as Calreticulin Transacetylase (CRTAase) that catalyzes the transfer of acetyl groups from polyphenolic acetates (PAs) to the receptor proteins and thus modulating their biological activities. In this communication, we have reported for the first time that acetoxy quinolones are endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. The correlation of specificity of platelet CRTAase to various analogues of acetoxy quinolones with intracellular NO and consequent effect on inhibition of platelet aggregation was considered crucial. Among acetoxy quinolones screened, 6-AQ (4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate/6-acetoxyquinolin-2-one, 22) was found to be the superior substrate to platelet CRTAase and emerged as the most active entity to produce antiplatelet action both in vitro and in vivo. 6-AQ caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2) and the inhibition of platelet aggregation. Structural modi. cation of acetoxy quinolones positively correlated with enhancement of intracellular NO and antiplatelet action. (C) 2010 Elsevier Ltd. All rights reserved.