3-(2-chlorophenyl)-6-fluoro-3,4-dihydroquinazolin-4-one-2-carboxaldehyde | 217942-80-8

• 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: 3-(2-chlorophenyl)-6-fluoro-3,4-dihydroquinazolin-4-one-2-carboxaldehyde
• 英文别名: 3-(2-chlorophenyl)-6-fluoro-4-oxoquinazoline-2-carbaldehyde
• CAS: 217942-80-8
• 化学式: C₁₅H₈ClFN₂O₂
• 分子量: 302.692
• InChiKey: SMDHYHLNRUHKBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-chlorophenyl)-6-fluoro-3,4-dihydroquinazolin-4-one-2-carboxaldehyde 在 乙酸酐 、 magnesium sulfate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 41.0h， 生成 N-[3-(2-chlorophenyl)-6-fluoro-4-oxo-3,4-dihydroquinazolin-2-ylmethyl]-N-(2-fluorophenyl)formamide
  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-甲基-3H-喹唑啉-4-酮 在 sodium periodate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-(2-chlorophenyl)-6-fluoro-3,4-dihydroquinazolin-4-one-2-carboxaldehyde
  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：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是苯并或噻吩融合芳香环；B是苯基、吡啶基或嘧啶基；X是N或CH；Y-Z是—CH2NH—或—NHCH2—；以及含有此类化合物的药物组合物，以及利用这些化合物来治疗神经退行性、精神药物、以及药物和酒精诱发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：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。
• 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。
• US6627755B1
  申请人：——

  公开号：US6627755B1

  公开（公告）日：2003-09-30
• US6921764B2
  申请人：——

  公开号：US6921764B2

  公开（公告）日：2005-07-26