2-chloro-6-nitro-N-propan-2-ylaniline | 124423-98-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-6-nitro-N-propan-2-ylaniline
• CAS: 124423-98-9
• 化学式: C₉H₁₁ClN₂O₂
• 分子量: 214.652
• InChiKey: PKTCQLKXVWUBFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-6-nitro-N-propan-2-ylaniline 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 44.0h， 生成 8-chloro-1,2,3,4-tetrahydro-1-isopropyl-2,3-dioxo-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：

  2-溴-3-氯硝基苯 、 异丙胺 反应 36.0h， 生成 2-chloro-6-nitro-N-propan-2-ylaniline
  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

• Imidazoquinoxaline compounds and their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0320136A2

  公开（公告）日：1989-06-14

  New imidazoquinoxaline compounds having the formula wherein X is CH, Chalogen or N; and R³ is or CO₂R′ wherein R′ is C₁₋₆ alkyl, C₃₋₇ cycloalkyl or (C₁₋₆ alkoxy)methyl are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics and hypnotics, and in improving the cognitive function of the brain of mammals.

  新的咪唑喹喔啉化合物，其式如下 其中 X 是 CH、卤素或 N；R³ 是 或 CO₂R′ 其中 R′为 C₁₋₆烷基、C₃₋₇环烷基或（C₁₋₆烷氧基）甲基，可用于精神药物制剂，作为抗惊厥药、抗焦虑药和催眠药，以及改善哺乳动物大脑的认知功能。
• US4968682A
  申请人：——

  公开号：US4968682A

  公开（公告）日：1990-11-06
• US4999354A
  申请人：——

  公开号：US4999354A

  公开（公告）日：1991-03-12