3-苯基-5H-咪唑并[1,5-a]喹喔啉-4-酮 | 531509-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-苯基-5H-咪唑并[1,5-a]喹喔啉-4-酮
• 英文名称: 3-phenylimidazo[1,5-a]quinoxalin-4(5H)-one
• 英文别名: 3-phenylimidazo[1,5-a]quionxalin-4(5H)-one；3-phenyl-5H-imidazo[1,5-a]quinoxalin-4-one
• CAS: 531509-85-0
• 化学式: C₁₆H₁₁N₃O
• 分子量: 261.283
• InChiKey: HFSBNVRRRXLTSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-苯基-5H-咪唑并[1,5-a]喹喔啉-4-酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 3-Phenyl-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+
• 作为产物：
  描述：

  N1-(叔丁基)苯-1,2-二胺 在 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 46.25h， 生成 3-苯基-5H-咪唑并[1,5-a]喹喔啉-4-酮
  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

• A short and efficient protocol for the synthesis of imidazo[1,5- a ]quinoxalin-4-ones from 3-aroylquinoxalinones and compounds with the aminomethylene moiety
  作者：Vakhid A. Mamedov、Aleksey A. Kalinin、Nataliya A. Zhukova、Victor V. Syakaev、Il'dar Kh. Rizvanov、Shamil K. Latypov、Oleg G. Sinyashin

  DOI：10.1016/j.tet.2014.11.017

  日期：2015.1

  The reaction of 3-aroylquinoxalin-2(1H)-ones with alpha-amino acids and their derivatives, amines with various alkyl groups, amino alcohols with alkylene groups of various length, N-(3-aminopropyl)morpholine and 1,6-diaminohexane in DMSO at 150 degrees C proceeds through the oxidative cyclocondensation and makes it possible to synthesize substituted imidazo[1,5-a]quinoxalines. Depending on the compound with the aminomethylene fragment used the reaction allows to introduction of any given substituent into position 1. (C) 2014 Elsevier Ltd. All rights reserved.
• ——
  作者：V. A. Mamedov、A. A. Kalinin、I. Kh. Rizvanov、N. M. Azancheev、Yu. Ya. Efremov、Ya. A. Levin

  DOI：10.1023/a:1021269602024

  日期：——
• ——
  作者：V. A. Mamedov

  DOI：10.1023/a:1023463117204

  日期：——

  Retrosynthetic analysis of the structure of imidazo[1,5-a]quinoxalines made it possible to develop new convenient procedures for preparation of these compounds by reaction of 3-(alpha-chlorobenzyl)-1,2-dihydroquinoxalin-2-one with potassium thiocyanate or isocyanate as synthetic equivalent of the two-membered N- = C+ building blocks and by reaction of 3-(alpha-aminobenzyl)-1,2-dihydroquinoxalin-2-one with carbon disulfide, triethoxymethane, aromatic aldehydes, or acetic anhydride as synthetic equivalent of the one-membered RC3+ synthon.
• 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.