(4-hydroxy-2-methylquinolin-3-yl)acetic acid | 848132-48-9

• 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: (4-hydroxy-2-methylquinolin-3-yl)acetic acid
• 英文别名: 2-(2-methyl-4-oxo-1H-quinolin-3-yl)acetic acid
• CAS: 848132-48-9
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: XUCPONCLMQPFBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±40.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-hydroxy-2-methylquinolin-3-yl)acetic acid 在 氯化亚砜 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.0h， 生成 N¹-[(4-hydroxy-2-methylquinolin-3-yl)acetyl]thiosemicarbazide
  参考文献：
  名称：

  New Quinoline Derivatives on the Basis of (4-Hydroxy-2-methylquinolin-3-yl)acetic Acid

  摘要：

  A procedure was developed for the synthesis of (4-hydroxy-2-methylquinolin-3-yl)acetic acid and the corresponding acyl chloride. Reactions of the latter with o-aminobenzenethiol, o-phenylenediamine, o-aminophenol, anthranilic acid, and thiosemicarbazide gave, respectively, 2-(4-hydroxy-2-methylquinolin-3ylmethyl)-1,3-benzothiazole, -benzoxazole, -benzimidazole, 2-(4-hydroxy-2-methylquinolin-3-ylmethyl)-4H3,1-benzoxazin-4-one, and 4-hydroxy-2-methyl-3-(5-sulfanyl-1H-1,2,4-triazol-3-ylmethyl)quinoline.

  DOI：

  10.1023/b:rujo.0000044555.03402.9b
• 作为产物：
  描述：

  乙酰琥珀酸二乙酯 在 二苯醚 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 26.5h， 生成 (4-hydroxy-2-methylquinolin-3-yl)acetic acid
  参考文献：
  名称：

  SYNTHESIS OF 2-METHYL4QUINOLONE-3-ACETIC ACIDS WITH POTENTIAL ANTIBACTERIAL ACTIVITY

  摘要：

  A number of quinolone-3-acetic acids were synthesized by cyclocondensation of substituted anilines with diethyl acetylsuccinate in the presence of phosphorous pentoxide and followed by base hydrolysis of the resultant esters to form respective acids. All synthesized compounds were found to exhibit antibacterial activities against a range of gram-positive (Bacillus subtilis Staphylococcus (aureus) and gram-negative bacteria (Shigella tunnel. Escherichia coli, Pseudomonas aeruginosa and Salmonella lyphi) by broth dilution method. All the compounds exhibited antibacterial activities comparable to fluoroquinolones and in some cases even better activity was found. These findings suggest a great potential of these compounds for screening and use as antibacterial compounds for further studies with a battery of bacteria.

  DOI：

  10.4067/s0717-97072012000300008

文献信息

• New Quinoline Derivatives on the Basis of (4-Hydroxy-2-methylquinolin-3-yl)acetic Acid
  作者：A. A. Avetisyan、I. L. Aleksanyan、A. A. Pivazyan

  DOI：10.1023/b:rujo.0000044555.03402.9b

  日期：2004.6

  A procedure was developed for the synthesis of (4-hydroxy-2-methylquinolin-3-yl)acetic acid and the corresponding acyl chloride. Reactions of the latter with o-aminobenzenethiol, o-phenylenediamine, o-aminophenol, anthranilic acid, and thiosemicarbazide gave, respectively, 2-(4-hydroxy-2-methylquinolin-3ylmethyl)-1,3-benzothiazole, -benzoxazole, -benzimidazole, 2-(4-hydroxy-2-methylquinolin-3-ylmethyl)-4H3,1-benzoxazin-4-one, and 4-hydroxy-2-methyl-3-(5-sulfanyl-1H-1,2,4-triazol-3-ylmethyl)quinoline.
• SYNTHESIS OF 2-METHYL4QUINOLONE-3-ACETIC ACIDS WITH POTENTIAL ANTIBACTERIAL ACTIVITY
  作者：Fauzia Anjum Chattha、Munawar Ali Munawar、Muhammad Ashraf、Saeed Ahmad Nagra、Mehr-Un-Nisa、Ismat Fatima

  DOI：10.4067/s0717-97072012000300008

  日期：——

  A number of quinolone-3-acetic acids were synthesized by cyclocondensation of substituted anilines with diethyl acetylsuccinate in the presence of phosphorous pentoxide and followed by base hydrolysis of the resultant esters to form respective acids. All synthesized compounds were found to exhibit antibacterial activities against a range of gram-positive (Bacillus subtilis Staphylococcus (aureus) and gram-negative bacteria (Shigella tunnel. Escherichia coli, Pseudomonas aeruginosa and Salmonella lyphi) by broth dilution method. All the compounds exhibited antibacterial activities comparable to fluoroquinolones and in some cases even better activity was found. These findings suggest a great potential of these compounds for screening and use as antibacterial compounds for further studies with a battery of bacteria.