3-(2-氯苯基)-6-氟-2-[[(2-氟苯基)氨基]甲基]-4(3H)-喹唑啉酮 | 217942-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-(2-氯苯基)-6-氟-2-[[(2-氟苯基)氨基]甲基]-4(3H)-喹唑啉酮
• 中文别名: 3-(2-氯苯基)-6-氟-2-[(2-氟苯基氨基)甲基]-3H-喹唑啉-4-酮
• 英文名称: 3-(2-chloro-phenyl)-6-fluoro-2-[(2-fluoro-phenylamino)-methyl]-3H-quinazolin-4-one
• 英文别名: 3-(2-Chlorophenyl)-6-fluoro-2-[(2-fluoroanilino)methyl]quinazolin-4-one
• CAS: 217942-71-7
• 化学式: C₂₁H₁₄ClF₂N₃O
• 分子量: 397.811
• InChiKey: CRTCTLBOOPUUJU-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180℃
• 密度：
  1.37

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-氯苯基)-6-氟-2-[[(2-氟苯基)氨基]甲基]-4(3H)-喹唑啉酮 在 硼烷四氢呋喃络合物 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 3-(2-chlorophenyl)-6-fluoro-2-[(2-fluoro-N-methylanilino)methyl]quinazolin-4-one
  参考文献：
  名称：

  Quinazolin-4-one α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptor Antagonists:  Structure−Activity Relationship of the C-2 Side Chain Tether

  摘要：

  A series of 6-fluoro-3-(2 -chlorophenyl)quinazolin-4-ones has been prepared, which contains a 2-fluorophenyl ring attached to C-2 by a variety of two-atom tethers. These compounds were used to probe the structure-activity relationship (SAR) for AMPA receptor inhibition. The relative potencies of the new compounds ranged from 11 nM. to greater than 10 muM. The differential activity of the compounds was rationalized on the basis of alterations of the 2-fluorophenyl positioning (planar and radial) relative to the quinazolin-4-one ring based on computational methods. From this effort, new AMPA receptor antagonists, containing the methylamino tether group, have been identified.

  DOI：

  10.1021/jm000522p
• 作为产物：
  描述：

  3-(2-氯苯基)-6-氟-2-(2-(二甲氨基)乙烯基)-3,4-二氢喹唑啉-4-酮 在 sodium periodate 、 magnesium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 22.0h， 生成 3-(2-氯苯基)-6-氟-2-[[(2-氟苯基)氨基]甲基]-4(3H)-喹唑啉酮
  参考文献：
  名称：

  Quinazolin-4-one α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptor Antagonists:  Structure−Activity Relationship of the C-2 Side Chain Tether

  摘要：

  A series of 6-fluoro-3-(2 -chlorophenyl)quinazolin-4-ones has been prepared, which contains a 2-fluorophenyl ring attached to C-2 by a variety of two-atom tethers. These compounds were used to probe the structure-activity relationship (SAR) for AMPA receptor inhibition. The relative potencies of the new compounds ranged from 11 nM. to greater than 10 muM. The differential activity of the compounds was rationalized on the basis of alterations of the 2-fluorophenyl positioning (planar and radial) relative to the quinazolin-4-one ring based on computational methods. From this effort, new AMPA receptor antagonists, containing the methylamino tether group, have been identified.

  DOI：

  10.1021/jm000522p

文献信息

• Quinazolin-4-one ampa antagonists
  申请人：Pfizer Inc

  公开号：US20040049039A1

  公开（公告）日：2004-03-11

  The present invention relates to novel quinazolin-4-one derivatives of the formula I, as defined in the specification, pharmaceutical compositions containing such compounds the use of such compounds to treat neurodegenerative, psychotropic, and drug and alcohol induced central and peripheral nervous system disorders.

  本发明涉及公式I中所定义的新型喹唑啉-4-酮衍生物，以及含有这些化合物的药物组合物，以及使用这些化合物来治疗神经退行性、精神药物、药物和酒精诱导的中枢和外周神经系统疾病。
• Quinazolin-4-one AMPA antagonists
  申请人：Pfizer INC

  公开号：US06627755B1

  公开（公告）日：2003-09-30

  The present invention relates to novel quinazolin-4-one derivatives of the formula wherein A is a benzo or thieno fused aromatic ring; B is phenyl, pyridyl or pyrimidyl; X is N or CH; and Y-Z is —CH2NH— or —NHCH2—; and to pharmaceutical compositions containing such compounds, and the use of such compounds to treat neurodegenerative, psychotropic, and drug and alcohol induced central and peripheral nervous system disorders.

  本发明涉及一种新型喹唑啉-4-酮衍生物，其化学式为：其中A为苯并或噻吩融合的芳香环；B为苯基、吡啶基或嘧啶基；X为N或CH；Y-Z为-CH2NH-或-NHCH2-；以及含有这种化合物的制药组合物，以及使用这种化合物治疗神经退行性、精神药物、药物和酒精引起的中枢和外周神经系统疾病。
• Thieno-pyrimidin-4-one AMPA antagonists
  申请人：Chenard Bertrand L

  公开号：US06921764B2

  公开（公告）日：2005-07-26

  The present invention relates to novel quinazolin-4-one derivatives of the formula I, as defined in the specification, pharmaceutical compositions containing such compounds the use of such compounds to treat neurodegenerative, psychotropic, and drug and alcohol induced central and peripheral nervous system disorders.

  本发明涉及式I所定义的新型喹唑啉-4-酮衍生物，以及含有这些化合物的药物组合物，用于治疗神经退行性、精神药物、药物和酒精诱导的中枢和外周神经系统疾病。
• AMPA antagonists for the treatment of dyskinesias associated with dopamine agonist therapy
  申请人：Pfizer Products Inc.

  公开号：EP0900568A2

  公开（公告）日：1999-03-10

  The invention relates to a method of treating dyskinesias associated with dopamine agonist therapy in a mammal which comprises administering to said mammal a compound, as defined herein, which is an antagonist of the AMPA receptor. Dopamine agonist therapy, as referred to in the present invention, is generally used in the treatment of a central nervous system disorder such as Parkinson's disease.

  本发明涉及一种治疗哺乳动物多巴胺激动剂治疗相关运动障碍的方法，该方法包括向所述哺乳动物施用本文所定义的化合物，该化合物是 AMPA 受体的拮抗剂。本发明所述的多巴胺激动剂疗法通常用于治疗帕金森病等中枢神经系统疾病。
• Modulation of AMPA/kainate Receptors for the Treatment of Hypoglycemia
  申请人：Vanderklish Peter

  公开号：US20200397751A1

  公开（公告）日：2020-12-24

  Methods for modulating the levels of glucagon and blood glucose of a mammal are provided. In the subject methods, a positive allosteric modulator of AMPA/kainate receptors is administered to a host. The subject methods find use in applications where it is desired to increase one or both of the glucagon and blood glucose levels in a mammalian host. The subject methods find use in applications where it is desired to decrease the size, or breadth, of the circadian range of blood glucose levels in a mammalian host. The subject methods also find use in applications where it is desired to decrease the frequency, severity, or occurrence of hypoglycemia in a mammalian host. Finally, the subject method finds use in applications where it is desired to decrease the frequency, severity, or occurrence of nocturnal hypoglycemia in a mammalian host, particularly that which occurs in diabetics as a result of therapy with insulins or insulin analogs or other glucose lowering agents, or combinations of such agents.