4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide | 60302-87-6

• 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-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide
• 英文别名: 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide；4-hydroxy-2-oxo-1H-quinoline-3-carbohydrazide
• CAS: 60302-87-6
• 化学式: C₁₀H₉N₃O₃
• 分子量: 219.2
• InChiKey: GQVZVVDVXKUTHT-UHFFFAOYSA-N

物化性质

• 熔点：
  >260 °C
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide 、 2,4-二氯苯甲酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到N'-(2,4-dichlorobenzoyl)-4-hydroxy-2-oxo-1,2-dihydro-3-quinolinecarbohydrazide
  参考文献：
  名称：

  4-hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids

  摘要：

  Two methods of preparation have been proposed and the synthesis has been effected of a large series of beta-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. The possibility of using various condensing agents for converting them into the corresponding 1,3,4-oxa-diazoloquinolines has been studied. Results are given of an investigation of the antitubercular activity of the synthesized compounds.

  DOI：

  10.1007/s10593-009-0198-6
• 作为产物：
  描述：

  2,4-二羟基喹啉-3-甲酸乙酯 在 肼 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以84%的产率得到4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis, biological assessment and molecular modeling of new dihydroquinoline-3-carboxamides and dihydroquinoline-3-carbohydrazide derivatives as cholinesterase inhibitors, and Ca channel antagonists

  摘要：

  The synthesis, biological evaluation, and molecular modeling of new 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides(4), 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6), and some hexahydropyrimido[5,4-c]quinoline-2,5-diones (9) produced earlier by our laboratory, as AChE/BuChE inhibitors, is described. From these analyses compound 4c resulted equipotent regarding the inhibition of cholinesterases'; inhibitors 6k, 9a, 9b were selective for AChE, whereas product 4d proved selective for BuChE. Docking analysis has been carry out in order to identify the binding mode in the active site, and to explain the observed selectivities. Only compound 9a has been shown to decrease K+-induced calcium signals in bovine chromaffin cells. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.054

文献信息

• 4-Hydroxy-2-quinolones 171*. Synthesis, isomerism, and antitubercular activity of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid alkylidenehydrazides
  作者：I. V. Ukrainets、Liu Yangyang、A. A. Tkach、A. V. Turov、O. S. Golovchenko

  DOI：10.1007/s10593-010-0431-3

  日期：2009.11

  Alkylidenehydrazides have been synthesized by the reaction of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazides with lower dialkyl ketones in order to reveal a structure-antitubercular activity relationship. It was shown by H-1 NMR spectroscopy that hydrazones obtained from the unsymmetrical ketone-methyl ethyl ketone-exist primarily in the E-isomer form. It was found that the presence of two aliphatic substituents in the alkylidene fragment of the compounds investigated leads to a marked lowering of antimicobacterial properties.
• 4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides
  作者：I. V. Ukrainets、L. V. Sidorenko、O. S. Golovchenko

  DOI：10.1007/s10593-007-0221-8

  日期：2007.11
• US4065481A
  申请人：——

  公开号：US4065481A

  公开（公告）日：1977-12-27
• US4144258A
  申请人：——

  公开号：US4144258A

  公开（公告）日：1979-03-13
• 4-hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids
  作者：I. V. Ukrainets、A. A. Tkach、Liu Yang Yang

  DOI：10.1007/s10593-009-0198-6

  日期：2008.11

  Two methods of preparation have been proposed and the synthesis has been effected of a large series of beta-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. The possibility of using various condensing agents for converting them into the corresponding 1,3,4-oxa-diazoloquinolines has been studied. Results are given of an investigation of the antitubercular activity of the synthesized compounds.