N-[3-(2-chlorophenyl)-6-fluoro-4-oxo-3,4-dihydroquinazolin-2-ylmethyl]-N-(2-fluorophenyl)formamide | 346700-98-9

• 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: N-[3-(2-chlorophenyl)-6-fluoro-4-oxo-3,4-dihydroquinazolin-2-ylmethyl]-N-(2-fluorophenyl)formamide
• 英文别名: N-[[3-(2-chlorophenyl)-6-fluoro-4-oxoquinazolin-2-yl]methyl]-N-(2-fluorophenyl)formamide
• CAS: 346700-98-9
• 化学式: C₂₂H₁₄ClF₂N₃O₂
• 分子量: 425.822
• InChiKey: FQQJWTRKOKTKOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 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：
  53
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[3-(2-chlorophenyl)-6-fluoro-4-oxo-3,4-dihydroquinazolin-2-ylmethyl]-N-(2-fluorophenyl)formamide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以30%的产率得到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-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