6-carboxy-3,4-dihydro-8-ethyl-2(1H)-quinolinone | 165592-20-1

• 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: 6-carboxy-3,4-dihydro-8-ethyl-2(1H)-quinolinone
• 英文别名: 6-carboxy-8-ethyl-3,4-dihydrocarbostyril；8-Ethyl-2-oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid；8-ethyl-2-oxo-3,4-dihydro-1H-quinoline-6-carboxylic acid
• CAS: 165592-20-1
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: FEMVNFLGQLZHRE-UHFFFAOYSA-N

物化性质

• 沸点：
  458.9±45.0 °C(Predicted)
• 密度：
  1.258±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：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基-N-(2-苯基乙基)-4-哌啶胺 、 6-carboxy-3,4-dihydro-8-ethyl-2(1H)-quinolinone 在 diethylphosphoryl cyanide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3,4-dihydro-8-ethyl-6-(4-(N-methyl-2-phenylethyl)amino-1-piperidinyl)carbonyl-2(1H)-quinolinone
  参考文献：
  名称：

  Novel Selective Hindlimb Vasodilators:  Synthesis and Biological Activity of 1-Acyl-4-aminopiperidine Derivatives

  摘要：

  A series of 6-(4-amino-1-piperidinyl)carbonyl-2(1H)-quinolinones, and their open form derivatives, were synthesized and evaluated for their ability to stimulate femoral artery blood flow (FBF) in the canine hindlimb. All members of this series stimulated FBF, and subsequent experiments revealed that selected members of this series produced minimal changes in coronary blood flow or systemic blood pressure. Compound 25 was the most promising agent in this respect, and clinical trials are now ongoing to evaluate the effectiveness of this drug as a novel treatment for intermittent claudication and Raynaud's phenomenon.

  DOI：

  10.1021/jm020597o
• 作为产物：
  描述：

  2-乙基苯胺 在 palladium on activated charcoal 吡啶 、 三氯化铝 、 氢气 、 potassium carbonate 作用下， 以 二硫化碳 、 水 、 溶剂黄146 、 氯苯 、 丙酮 为溶剂， 20.0~90.0 ℃ 、101.33 kPa 条件下， 反应 5.5h， 生成 6-carboxy-3,4-dihydro-8-ethyl-2(1H)-quinolinone
  参考文献：
  名称：

  Novel Selective Hindlimb Vasodilators:  Synthesis and Biological Activity of 1-Acyl-4-aminopiperidine Derivatives

  摘要：

  A series of 6-(4-amino-1-piperidinyl)carbonyl-2(1H)-quinolinones, and their open form derivatives, were synthesized and evaluated for their ability to stimulate femoral artery blood flow (FBF) in the canine hindlimb. All members of this series stimulated FBF, and subsequent experiments revealed that selected members of this series produced minimal changes in coronary blood flow or systemic blood pressure. Compound 25 was the most promising agent in this respect, and clinical trials are now ongoing to evaluate the effectiveness of this drug as a novel treatment for intermittent claudication and Raynaud's phenomenon.

  DOI：

  10.1021/jm020597o

文献信息

• Peripheral vasodilators
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05591751A1

  公开（公告）日：1997-01-07

  Peripheral vasodilating agents containing, as the active ingredient, carbostyril derivatives represented by the general formula: ##STR1## or a salt thereof; and novel carbostyril derivatives included within the scope of the above-mentioned general formula.

  含有周围血管扩张剂的药物，活性成分为一般式表示的卡波司烯衍生物，或其盐；以及包含在上述一般式范围内的新型卡波司烯衍生物。
• PIPERAZINOCARBONYLCARBOSTYRILS AS PERIPHERAL VASODILATORS
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0636128A1

  公开（公告）日：1995-02-01
• US5591751A
  申请人：——

  公开号：US5591751A

  公开（公告）日：1997-01-07
• [EN] PIPERAZINOCARBONYLCARBOSTYRILS AS PERIPHERAL VASODILATORS<br/>[FR] UTILISATION DE PIPERAZINOCARBONYLCARBOSTYRILES COMME VASODILATATEURS PERIPHERIQUES
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：WO1994019339A1

  公开（公告）日：1994-09-01

  (EN) The present invention provides novel peripheral vasodilating agents and novel carbostyril derivatives having peripheral vasodilating activity. Peripheral vasodilating agents containing, as the active ingredient, carbostyril derivatives represented by general formula (1) or salt thereof; and novel carbostyril derivatives which are included within the scope of the above-mentioned general formula.(FR) La présente invention concerne de nouveaux agents de vasodilatation périphérique et de nouveaux dérivés de carbostyrile ayant une activité de vasodilatation périphérique. Agents de vasodilatation périphérique contenant, comme ingrédient actif, des dérivés de carbostyrile représentés par la formule générale (1), ou sel tiré de ces dérivés; et nouveaux dérivés du carbostyrile, inclus dans ladite formule générale.