3-乙基-7-羟基-4-甲基-2(1H)-喹啉酮 | 354130-78-2

• 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-乙基-7-羟基-4-甲基-2(1H)-喹啉酮
• 英文名称: 3-ethyl-7-hydroxy-4-methylquinolin-2(1H)-one
• 英文别名: 3-ethyl-7-hydroxy-4-methyl-1H-quinolin-2-one
• CAS: 354130-78-2
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: SWQKXCSLQZOANW-UHFFFAOYSA-N

物化性质

• 熔点：
  250-252 °C
• 沸点：
  420.0±45.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-溴十一酰氯 、 3-乙基-7-羟基-4-甲基-2(1H)-喹啉酮 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 3-ethyl-4-methyl-2-oxo-1,2-dihydroquinolin-7-yl 11-bromoundecanoate
  参考文献：
  名称：

  Ammonium derivatives of chromenones and quinolinones as lead antimicrobial agents

  摘要：

  一系列新型铵类衍生物被合成并检测其抗微生物效果。抗微生物谱的比较显示，化合物9、11、16和23在体外对病原体具有强大的潜力。细胞毒性结果表明，化合物9是毒性最低的，在MTT实验中对A549和U87细胞无毒，并且在1000 μg/ml浓度下对人类红细胞表现出边缘毒性（15%–20%），而与之相比，标准药物两性霉素B在31.25 μg/ml时会导致100%细胞溶解。该化合物在不同病原体的DDA中显示出1.95–31.25 μg/盘的最小抑菌浓度（MIC），可被视为进一步探索的重要抗微生物先导分子。

  DOI：

  10.1007/s12039-011-0147-7
• 作为产物：
  描述：

  3-ethyl-7-methoxy-4-methylquinolin-2(1H)-one 在 氢溴酸 、 溶剂黄146 作用下， 反应 75.0h， 以70%的产率得到3-乙基-7-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

• Byvanck, Chemische Berichte, 1898, vol. 31, p. 2153
  作者：Byvanck

  DOI：——

  日期：——
• 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.
• Ammonium derivatives of chromenones and quinolinones as lead antimicrobial agents
  作者：SHILPI GUPTA、SEEMA SINGH、ABHA KATHURIA、MANISH KUMAR、SWETA SHARMA、RAM KUMAR、VIRINDER S PARMAR、BHARAT SINGH、ANJALI GUPTA、ERIK VAN DER EYCKEN、GAINDA L SHARMA、SUNIL K SHARMA

  DOI：10.1007/s12039-011-0147-7

  日期：2012.3

  A series of novel ammonium derivatives were synthesized and examined for their antimicrobial efficacy. Comparison of antimicrobial spectrum revealed that compounds 9, 11, 16 and 23 had strong potential against pathogens in vitro. Cytotoxicity results showed compound 9 to be least toxic, it is non-toxic to A549 and U87 cells in MTT assay and exhibits marginal toxicity (15–20%) to human erythrocytes at a concentration of 1000 μg/ml as compared to 100% lysis of cells by 31.25 μg/ml of the standard drug amphotericin B. This compound has MIC values in the range of 1.95–31.25 μg/disc in DDA against different pathogens and may considered to be an important lead antimicrobial molecule for further exploration.

  一系列新型铵类衍生物被合成并检测其抗微生物效果。抗微生物谱的比较显示，化合物9、11、16和23在体外对病原体具有强大的潜力。细胞毒性结果表明，化合物9是毒性最低的，在MTT实验中对A549和U87细胞无毒，并且在1000 μg/ml浓度下对人类红细胞表现出边缘毒性（15%–20%），而与之相比，标准药物两性霉素B在31.25 μg/ml时会导致100%细胞溶解。该化合物在不同病原体的DDA中显示出1.95–31.25 μg/盘的最小抑菌浓度（MIC），可被视为进一步探索的重要抗微生物先导分子。