7-(3-Aminomethyl-1-pyrrolyl)-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione | 192120-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-(3-Aminomethyl-1-pyrrolyl)-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione
• 英文别名: 6-[3-(Aminomethyl)pyrrol-1-yl]-7-(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dione
• CAS: 192120-96-0
• 化学式: C₁₄H₁₁F₃N₄O₂
• 分子量: 324.262
• InChiKey: VIROLUKPVOVJDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  89.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(3-Aminomethyl-1-pyrrolyl)-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N'-(4-Carboxyphenyl)-N-(1-(6-trifluoromethylquinoxaline-2,3-(1H,4H) dion-7-yl)pyrrol-3-ylmethyl)urea
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: Dicarboxylates as highly potent AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones carrying carboxylates at the pyrrole side-chain were synthesized and evaluated for AMPA receptor binding and for selectivity over other glutamate receptors. Particularly dicarboxy derivatives represent selective and highly potent AMPA antagonists. Moreover, several compounds displayed a remarkable efficacy against AMPA induced lethal convulsions and maximal electroshock seizures (MES) in mice. The good in vivo efficacy of the highly polar compounds suggests the involvement of an active transport mechanism. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00428-9
• 作为产物：
  描述：

  6-amino-7-trifluoromethyl-2,3(1H,4H)-quinoxalinedione 在 lithium hydroxide 、 溶剂黄146 作用下， 反应 0.5h， 生成 7-(3-Aminomethyl-1-pyrrolyl)-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: The importance of pyrrolic substitution on AMPA receptor binding

  摘要：

  Pyrrolylquinoxalinediones were synthesized to elucidate the value of pyrrolic substitution pattern on AMPA receptor binding. We discovered that amide and urea residues at the 3'-position at pyrrol ring favor affinity to AMPA receptor. Particularly, the phenylurea 13n exhibited a K-i value of 4 nM in AMPA receptor binding and represents the most potent competitive AMPA antagonist reported to dare. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00170-4

文献信息

• Pyrrolyl quinoxalindiones their production and use as AMPA receptor antagonists
  申请人：Abbott Laboratories

  公开号：US06277850B1

  公开（公告）日：2001-08-21

  Pyrrolylquinoxalinediones of the formula I and their tautomeric and isomeric forms, and their physiologically tolerated salts are described, where the variables have the following meaning: R1 hydrogen, C1-C6-alkyl, substituted by hydroxyl or carboxyl, R2 hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, a chlorine, fluorine or bromine atom, a trihalomethyl, cyano or nitro group or SO2—C1-C4-alkyl, R3 COOH or a radical which can be hydrolyzed to the carboxyl group, n 1 or 2.

  公式I的吡咯基喹喔啉二酮及其互变异构和同分异构形式以及其生理耐受的盐已被描述，其中变量的含义如下：R1为氢、C1-C6-烷基，被羟基或羧基取代，R2为氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、氯、氟或溴原子、三卤甲基、氰基或硝基，或SO2—C1-C4-烷基，R3为COOH或可水解为羧基的基团，n为1或2。
• US6277850B1
  申请人：——

  公开号：US6277850B1

  公开（公告）日：2001-08-21
• Pyrrolylquinoxalinediones: The importance of pyrrolic substitution on AMPA receptor binding
  作者：W. Lubisch、B. Benl、H.P. Hofmann

  DOI：10.1016/s0960-894x(97)00170-4

  日期：1997.5

  Pyrrolylquinoxalinediones were synthesized to elucidate the value of pyrrolic substitution pattern on AMPA receptor binding. We discovered that amide and urea residues at the 3'-position at pyrrol ring favor affinity to AMPA receptor. Particularly, the phenylurea 13n exhibited a K-i value of 4 nM in AMPA receptor binding and represents the most potent competitive AMPA antagonist reported to dare. (C) 1997 Elsevier Science Ltd.
• Pyrrolylquinoxalinediones: Dicarboxylates as highly potent AMPA receptor antagonists
  作者：W. Lubisch、B. Behl、H.P. Hofmann、H.J. Teschendorf

  DOI：10.1016/s0960-894x(97)00428-9

  日期：1997.10

  Pyrrolylquinoxalinediones carrying carboxylates at the pyrrole side-chain were synthesized and evaluated for AMPA receptor binding and for selectivity over other glutamate receptors. Particularly dicarboxy derivatives represent selective and highly potent AMPA antagonists. Moreover, several compounds displayed a remarkable efficacy against AMPA induced lethal convulsions and maximal electroshock seizures (MES) in mice. The good in vivo efficacy of the highly polar compounds suggests the involvement of an active transport mechanism. (C) 1997 Elsevier Science Ltd.