8-羟基-4-甲基-2(1h)-喹啉酮 | 30198-02-8

• 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: 8-羟基-4-甲基-2(1h)-喹啉酮
• 中文别名: 8-羟基-4-甲基-2(1H)-喹啉酮
• 英文名称: 8-hydroxy-4-methylquinolin-2(1H)-one
• 英文别名: 8-Hydroxy-4-methyl-2-chinolon；8-hydroxy-4-methyl-1H-quinolin-2-one；8-hydroxy-4-methyl-1H-quinolin-2-one
• CAS: 30198-02-8
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: IAJITIBCIXRYTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  8-羟基-4-甲基-2(1h)-喹啉酮 在 potassium dichromate 、 硫酸 作用下， 以 氯仿 、 水 为溶剂， 以44%的产率得到4-methyl-2,5,8(1H)-quinolinetrione
  参考文献：
  名称：

  A Comparative Study of Synthetic Approaches to 1-Methyl-2,5,8(1H)-quinolinetrione and 4-Methyl-2,5,8(1H)-quinolinetrione

  摘要：

  1-甲基-2,5,8(1H)-喹啉三酮的最佳总产率是通过对1-甲基-8-羟基-2-喹啉进行重铬酸盐氧化获得的。4-甲基-2,5,8(1H)-喹啉三酮是通过对2,5-二甲氧基苯胺进行乙酰乙酰化，使用2,2,6-三甲基-4H-1,3-二噁烷-4-酮，随后用铈铵硝酸盐氧化合成的。

  DOI：

  10.1055/s-1991-26557
• 作为产物：
  描述：

  2-羟基-4-甲基-8-甲氧基喹啉 在 氢溴酸 、 溶剂黄146 作用下， 反应 75.0h， 以70%的产率得到8-羟基-4-甲基-2(1h)-喹啉酮
  参考文献：
  名称：

  Characterization of 4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate as an effective antiplatelet agent

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.04.011

文献信息

• Synthesis of Coordinatively Unsaturated Iridium Complexes Having Functional 8-Quinolinolato Ligands: New Catalysts for Dehydrogenative Oxidation of Alcohols in Aqueous Media
  作者：Kazuki Toyomura、Ken-ichi Fujita

  DOI：10.1246/cl.170166

  日期：2017.6.5

  these new complexes had coordinatively unsaturated structure (five-coordinate trivalent iridium: 16e− complex). Furthermore, one of the new complexes exhibited high catalytic activity for the dehydrogenative oxidation of various aromatic and aliphatic secondary alcohols in aqueous media to give the corresponding ketones in good to excellent yields.

  已经合成了具有功能性 8-喹啉基配体的新型铱配合物。通过单晶X射线分析，发现这些新配合物具有配位不饱和结构（五配位三价铱：16e-配合物）。此外，其中一种新配合物对水性介质中各种芳香族和脂肪族仲醇的脱氢氧化表现出很高的催化活性，从而以良好到优异的产率得到相应的酮。
• 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。
• CDC25 inhibitors
  申请人：InterMed Discovery GmbH

  公开号：EP2130831A1

  公开（公告）日：2009-12-09

  The invention relates to pyridoquinolones, their synthesis and pharmaceutical use. The pyridoquinolones are useful as CDC25 inhibitors.

  本发明涉及吡啶并喹啉酮及其合成和药物用途。所述吡啶并喹啉酮作为CDC25抑制剂具有应用价值。
• NOVEL COMPOUND WITH ANTIBACTERIAL ACTIVITY
  申请人：JUNTENDO EDUCATIONAL FOUNDATION

  公开号：US20160257651A1

  公开（公告）日：2016-09-08

  A compound represented by the general formula (I) or a salt thereof having a potent antibacterial activity against bacteria that have acquired resistance to quinolones, and a medicament for prophylactic and/or therapeutic treatment of an infectious disease containing the compound or a salt thereof as an active ingredient, as well as a medicament for prophylactic and/or therapeutic treatment of an infectious disease containing a combination of the compound or a salt thereof, and a quinolone.

  一种由通式（I）表示的化合物或其盐，具有对已获得对喹诺酮抗性的细菌具有强效的抗菌活性，以及一种用该化合物或其盐作为活性成分的预防和/或治疗感染性疾病的药物，以及一种包含该化合物或其盐与喹诺酮的组合物作为活性成分的预防和/或治疗感染性疾病的药物。
• 1,2-Dihydro-chinolin-2-on-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0006506A1

  公开（公告）日：1980-01-09

  Die Erfindung betrifft 1,2-Dihydro-chinolin-2-on-Derivate mit antiallergischer Wirkung, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende Arzneimittel. Die Herstellung der erfindungsgemäßen Substanzen erfolgt durch Umsetzen von Hydroxy-1,2-dihydrochinolin-2-onen mit reaktiven N-Alkyl-piperazinen bzw. von reaktiven Alkoxy-1,2-di- hydro-chinolin-2-onen mit Piperazin-Derivaten.

  本发明涉及具有抗过敏活性的1,2-二氢喹啉-2-酮衍生物、制备这些化合物的工艺以及含有这些化合物的药物。根据本发明的物质是通过羟基-1,2-二氢喹啉-2-酮与活性 N-烷基哌嗪或活性烷氧基-1,2-二氢喹啉-2-酮与哌嗪衍生物反应制备的。