3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxaline | 148858-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxaline
• CAS: 148858-16-6
• 化学式: C₁₆H₁₂FN₃
• 分子量: 265.29
• InChiKey: IWPFRGQOSJWAOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxaline 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl 3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxaline-5-carboxylate
  参考文献：
  名称：

  3-Phenyl-Substituted Imidazo[1,5-a]quinoxalin-4-ones and Imidazo[1,5-a]quinoxaline Ureas That Have High Affinity at the GABA_A/Benzodiazepine Receptor Complex

  摘要：

  A series of imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alpha]quinoxaline ureas containing substituted phenyl groups at the 3-position was developed. Compounds within the imidazo-[1,5-alpha]quinoxaline urea series had high affinity for the GABA(A)/benzodiazepine receptor complex with varying in vitro efficacy, although most analogs were partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Interestingly, a subseries of piperazine ureas was identified which had biphasic efficacy, becoming more antagonistic with increasing concentration. Analogs within the imidazo [1,5-alpha] quinoxalin-4-one series had substantially decreased binding affinity as compared to the quinoxaline urea series. These compounds ranged from antagonists to full agonists by in. vitro analysis, with several derivatives having roughly 4-fold greater intrinsic activity than diazepam as indicated by Cl- current measurement. Numerous compounds from both series were effective in antagonizing metrazole-induced seizures, consistent with anti-convulsant properties and possible anxiolytic activity. Most of the quinoxaline ureas and quinoxalin-4-ones were active in an acute electroshock physical dependence side effect assay in mice precluding further development.

  DOI：

  10.1021/jm960070+
• 作为产物：
  描述：

  N1-(叔丁基)苯-1,2-二胺 在 dimethyl sulfide borane 、 potassium tert-butylate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 140.25h， 生成 3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxaline
  参考文献：
  名称：

  3-Phenyl-Substituted Imidazo[1,5-a]quinoxalin-4-ones and Imidazo[1,5-a]quinoxaline Ureas That Have High Affinity at the GABA_A/Benzodiazepine Receptor Complex

  摘要：

  A series of imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alpha]quinoxaline ureas containing substituted phenyl groups at the 3-position was developed. Compounds within the imidazo-[1,5-alpha]quinoxaline urea series had high affinity for the GABA(A)/benzodiazepine receptor complex with varying in vitro efficacy, although most analogs were partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Interestingly, a subseries of piperazine ureas was identified which had biphasic efficacy, becoming more antagonistic with increasing concentration. Analogs within the imidazo [1,5-alpha] quinoxalin-4-one series had substantially decreased binding affinity as compared to the quinoxaline urea series. These compounds ranged from antagonists to full agonists by in. vitro analysis, with several derivatives having roughly 4-fold greater intrinsic activity than diazepam as indicated by Cl- current measurement. Numerous compounds from both series were effective in antagonizing metrazole-induced seizures, consistent with anti-convulsant properties and possible anxiolytic activity. Most of the quinoxaline ureas and quinoxalin-4-ones were active in an acute electroshock physical dependence side effect assay in mice precluding further development.

  DOI：

  10.1021/jm960070+

文献信息

• Imidazo[1,5-A]quinoxalines
  申请人：The Upjohn Company

  公开号：US05541324A1

  公开（公告）日：1996-07-30

  An invention relating to Imidazo[1,5-a]quinoxalines (I) ##STR1## which do not contain an endocyclic carbonyl group and which are useful as anxiolytic and sedative/hypnotic agents.

  一种涉及咪唑并[1,5-a]喹喔啉(I)的发明，不含内环羰基，并且可用作抗焦虑和镇静/催眠剂。
• 4,5-cyclicimidazo[1,5-A]quinoxalines
  申请人：Pharmacia & Upjohn Company

  公开号：US05668282A1

  公开（公告）日：1997-09-16

  The invention discloses imidazo[1,5-a]quinoxalines (I) ##STR1## which do not contain an endocyclic carbonyl group that are useful as anxiolytic and sedative/hypnotic agents.

  本发明揭示了不含内环羰基的咪唑[1,5-a]喹啉(I) ##STR1## 作为抗焦虑和镇静/催眠剂使用。
• 5,6-cyclicimidazo [1,5-a] Quinoxalines
  申请人：The Upjohn Company

  公开号：US05574038A1

  公开（公告）日：1996-11-12

  The invention discloses imidazo[1,5-a]quinoxalines (I) ##STR1## which do not contain an endocyclic carbonyl group that are useful as anxiolytic and sedative/hypnotic agents.

  本发明揭示了不含内环羰基的咪唑并[1,5-a]喹啉(I) ##STR1## 作为抗焦虑和镇静/催眠剂。
• 3-Phenyl-Substituted Imidazo[1,5-<i>a</i>]quinoxalin-4-ones and Imidazo[1,5-<i>a</i>]quinoxaline Ureas That Have High Affinity at the GABA_A/Benzodiazepine Receptor Complex
  作者：E. Jon Jacobsen、Lindsay S. Stelzer、Kenneth L. Belonga、Donald B. Carter、Wha Bin Im、Vimala H. Sethy、Andrew H. Tang、Philip F. VonVoigtlander、James D. Petke

  DOI：10.1021/jm960070+

  日期：1996.1.1

  A series of imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alpha]quinoxaline ureas containing substituted phenyl groups at the 3-position was developed. Compounds within the imidazo-[1,5-alpha]quinoxaline urea series had high affinity for the GABA(A)/benzodiazepine receptor complex with varying in vitro efficacy, although most analogs were partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Interestingly, a subseries of piperazine ureas was identified which had biphasic efficacy, becoming more antagonistic with increasing concentration. Analogs within the imidazo [1,5-alpha] quinoxalin-4-one series had substantially decreased binding affinity as compared to the quinoxaline urea series. These compounds ranged from antagonists to full agonists by in. vitro analysis, with several derivatives having roughly 4-fold greater intrinsic activity than diazepam as indicated by Cl- current measurement. Numerous compounds from both series were effective in antagonizing metrazole-induced seizures, consistent with anti-convulsant properties and possible anxiolytic activity. Most of the quinoxaline ureas and quinoxalin-4-ones were active in an acute electroshock physical dependence side effect assay in mice precluding further development.