6-chloroacetyl-3,4-dihydro-8-methyl-2(1H)-quinolinone | 148136-16-7

• 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-chloroacetyl-3,4-dihydro-8-methyl-2(1H)-quinolinone
• 英文别名: 6-(2-chloroacetyl)-8-methyl-3,4-dihydro-1H-quinolin-2-one
• CAS: 148136-16-7
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: FRLUMJFQWARGLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloroacetyl-3,4-dihydro-8-methyl-2(1H)-quinolinone 在 吡啶 、 sodium hydroxide 作用下， 反应 2.0h， 以60%的产率得到6-carboxy-3,4-dihydro-8-methyl-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：

  3,4-二氢-8-甲基-2(1H)-喹啉酮 、 氯乙酰氯 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 以95%的产率得到6-chloroacetyl-3,4-dihydro-8-methyl-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

• Dérivés de 2-(pipéridin-1-y1) éthanol, leur préparation et leur application en thérapeutique
  申请人：SYNTHELABO

  公开号：EP0524846A1

  公开（公告）日：1993-01-27

  Composé, sous forme d'isomère optique pur ou de mélange de deux énantiomères, répondant à la formule générale (I) dans laquelle R₁ représente un atome d'hydrogène ou d'halogène ou un groupe méthyle, R₂ représente un ou deux substituants choisis parmi les atomes d'hydrogène et d'halogènes et les groupes (C₁₋₄)alkyle, hydroxy, (C₁₋₄)alcoxy, trifluorométhyle, acétylamino et méthylsulfonylamino, et soit X représente un groupe CH₂ et Y représente un groupe CH₂, (CH₂)₂ ou CO, soit X représente un groupe CO et Y représente un groupe CH₂.

  符合通式(I)的纯光学异构体或两种对映体混合物形式的化合物 其中 R₁ 代表氢原子、卤素原子或甲基，R₂ 代表一个或两个取代基，选自氢和卤素原子以及 (C₁₋₄)烷基、羟基、(C₁₋₄)烷氧基、三氟甲基、乙酰氨基和甲磺酰氨基，并且 X 代表 CH₂ 基团，Y 代表 CH₂、(CH₂)₂ 或 CO 基团，或者 X 代表 CO 基团，Y 代表 CH₂ 基团。
• Novel Selective Hindlimb Vasodilators:  Synthesis and Biological Activity of 1-Acyl-4-aminopiperidine Derivatives
  作者：Shuji Teramoto、Michinori Tanaka、Hiroshi Shimizu、Takafumi Fujioka、Fujio Tabusa、Takashi Imaizumi、Kenji Yoshida、Hiroyuki Fujiki、Toyoki Mori、Takumi Sumida、Michiaki Tominaga

  DOI：10.1021/jm020597o

  日期：2003.7.1

  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.