6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-4-(pyrrolidinocarbonyl)quinoxalin-2-one | 173165-55-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-4-(pyrrolidinocarbonyl)quinoxalin-2-one
• 英文别名: 6-chloro-3,3-dimethyl-4-(pyrrolidine-1-carbonyl)-1H-quinoxalin-2-one
• CAS: 173165-55-4
• 化学式: C₁₅H₁₈ClN₃O₂
• 分子量: 307.78
• InChiKey: IPUJOLLTEJARBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-4-(pyrrolidinocarbonyl)quinoxalin-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 18.25h， 生成 7-Chloro-3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydro-4,4-dimethyl-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline
  参考文献：
  名称：

  High-Affinity Partial Agonist Imidazo[1,5-a]quinoxaline Amides, Carbamates, and Ureas at the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex

  摘要：

  A series of imidazo[1,5-alpha]quinoxaline amides, carbamates, and ureas which have high affinity for the gamma-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies racing from antagonists to full agonists. However, most analogs were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Many of these compounds were also effective in antagonizing metrazole-induced seizures in accordance with anticonvulsant and possible anxiolytic activity. Selected quinoxalines displayed limited benzodiazepine-type side effects such as ethanol potentiation and physical dependence in animal models. Dimethylamino urea 41 emerged as the most interesting analog, having a partial agonist profile in vitro while possessing useful activity in animal models of anxiety such as the Vogel and Geller assays. In accordance with its partial agonist profile, 41 was devoid of typical benzodiazepine side effects.

  DOI：

  10.1021/jm940765f
• 作为产物：
  描述：

  2--2-methyl-1-propanol 在 咪唑 、 jones reagent 、 titanium(III) chloride 、 sodium acetate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 130.5h， 生成 6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-4-(pyrrolidinocarbonyl)quinoxalin-2-one
  参考文献：
  名称：

  High-Affinity Partial Agonist Imidazo[1,5-a]quinoxaline Amides, Carbamates, and Ureas at the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex

  摘要：

  A series of imidazo[1,5-alpha]quinoxaline amides, carbamates, and ureas which have high affinity for the gamma-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies racing from antagonists to full agonists. However, most analogs were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Many of these compounds were also effective in antagonizing metrazole-induced seizures in accordance with anticonvulsant and possible anxiolytic activity. Selected quinoxalines displayed limited benzodiazepine-type side effects such as ethanol potentiation and physical dependence in animal models. Dimethylamino urea 41 emerged as the most interesting analog, having a partial agonist profile in vitro while possessing useful activity in animal models of anxiety such as the Vogel and Geller assays. In accordance with its partial agonist profile, 41 was devoid of typical benzodiazepine side effects.

  DOI：

  10.1021/jm940765f

文献信息

• High-Affinity Partial Agonist Imidazo[1,5-<i>a</i>]quinoxaline Amides, Carbamates, and Ureas at the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex
  作者：E. Jon Jacobsen、Ruth E. TenBrink、Lindsay S. Stelzer、Kenneth L. Belonga、Donald B. Carter、Haesook K. Im、Wha Bin Im、Vimala H. Sethy、Andy H. Tang、Philip F. VonVoigtlander、James D. Petke

  DOI：10.1021/jm940765f

  日期：1996.1.1

  A series of imidazo[1,5-alpha]quinoxaline amides, carbamates, and ureas which have high affinity for the gamma-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies racing from antagonists to full agonists. However, most analogs were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Many of these compounds were also effective in antagonizing metrazole-induced seizures in accordance with anticonvulsant and possible anxiolytic activity. Selected quinoxalines displayed limited benzodiazepine-type side effects such as ethanol potentiation and physical dependence in animal models. Dimethylamino urea 41 emerged as the most interesting analog, having a partial agonist profile in vitro while possessing useful activity in animal models of anxiety such as the Vogel and Geller assays. In accordance with its partial agonist profile, 41 was devoid of typical benzodiazepine side effects.