3-(2-chloro-phenyl)-6-fluoro-2-[2-(2-fluoro-phenyl)-vinyl]-3H-quinazolin-4-one | 346700-90-1

• 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-chloro-phenyl)-6-fluoro-2-[2-(2-fluoro-phenyl)-vinyl]-3H-quinazolin-4-one
• 英文别名: 3-(2-chlorophenyl)-6-fluoro-2-[(E)-2-(2-fluorophenyl)ethenyl]quinazolin-4-one
• CAS: 346700-90-1
• 化学式: C₂₂H₁₃ClF₂N₂O
• 分子量: 394.808
• InChiKey: XERYSIDAXRXLBX-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-chloro-phenyl)-6-fluoro-2-[2-(2-fluoro-phenyl)-vinyl]-3H-quinazolin-4-one 在 10percent Pd/C 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以66%的产率得到3-(2-Chloro-phenyl)-6-fluoro-2-[2-(2-fluoro-phenyl)-ethyl]-3H-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：

  2-氟苯甲醛 、 3-(2-氯-苯基)-6-氟-2-甲基-3H-喹唑啉-4-酮 在 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 以57%的产率得到3-(2-chloro-phenyl)-6-fluoro-2-[2-(2-fluoro-phenyl)-vinyl]-3H-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

文献信息

• Methods of preparing substituted 3-phenyl- and 3-pyridyl-4(3H)-quinazolinones and atropisomers thereof
  申请人：Pfizer Products Inc.

  公开号：EP0934934A2

  公开（公告）日：1999-08-11

  This invention is directed to methods for the preparation of quinazolin-4-one derivatives of the formula and the pharmaceutically acceptable salts and atropisomers of the formula and the pharmaceutically acceptable salts thereof, wherein Ar, R1, R2, X and Y are as defined in the specification. The quinazolin-4-one derivatives prepared according to the methods of this invention are α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) inhibitors and are useful for the treatment of various neurologic disorders and conditions including Parkinson's Disease, epilepsy, emesis, eschemia, stroke, traumatic brain and spinal cord injury, and so forth. The present invention also relates to compounds of the formulae

  本发明涉及制备式中的喹唑啉-4-酮衍生物以及式中的药物可接受盐和异构体的方法 及其药学上可接受的盐和式中的异构体的方法。 及其药学上可接受的盐，其中 Ar、R1、R2、X 和 Y 如说明书中所定义。根据本发明方法制备的喹唑啉-4-酮衍生物是α-氨基-3-羟基-5-甲基-4-异噁唑丙酸（AMPA）抑制剂，可用于治疗各种神经系统疾病和病症，包括帕金森病、癫痫、呃逆、衄血、中风、脑外伤和脊髓损伤等。 本发明还涉及式中的化合物
• 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
  作者：Bertrand L. Chenard、Willard M. Welch、James F. Blake、Todd W. Butler、Anthony Reinhold、Frank E. Ewing、Frank S. Menniti、Martin J. Pagnozzi

  DOI：10.1021/jm000522p

  日期：2001.5.1

  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.