3-fluoro-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid | 87808-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-fluoro-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid
• 英文别名: 4-[(4-Acetyl-3-hydroxy-2-propylphenoxy)methyl]-3-fluorobenzoic acid
• CAS: 87808-06-8
• 化学式: C₁₉H₁₉FO₅
• 分子量: 346.355
• InChiKey: ODQDUWUBFVPBNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-二羟基-3-丙基苯乙酮 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 生成 3-fluoro-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid
  参考文献：
  名称：

  Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes

  摘要：

  Considerations of the possible similarities between leukotriene D4 and its prototypical antagonist, FPL 55712, led to the development of a new series of leukotriene antagonists incorporating a hydroxyacetophenone group (e.g., the toluic acids 16 and 18). Although considerable attention has focused on FPL 55712-derived analogues, only limited investigations into alternatives for the standard 4-acetyl-3-hydroxy-2-propylphenoxy moiety have been reported. Therefore, an extensive study of modifications to the hydroxyacetophenone portion of toluic acid 18 was undertaken. Although no viable alternative to the 3-hydroxy moiety was discovered, replacements for the 2-propyl group (34, 37) and the 4-acetyl functionality (56, 59) yielded potent antagonists. A number of compounds exhibited longer duration of action in vivo than FPL 55712.

  DOI：

  10.1021/jm00124a014

文献信息

• Pharmaceutically active phenylcarboxylic acid derivatives
  申请人：ICI AMERICAS INC.

  公开号：EP0083228A1

  公开（公告）日：1983-07-06

  Compounds which antagonize the slow-reacting substance of anaphylaxis or components thereof, e.g., leukotrienes, in warm blooded animals as well as intermediates and methods for their preparation, pharmaceutical compositions and method for their administration. The compounds are diphenyl carboxylic acids with particular linking groups between the individual phenyl rings and the carboxylic acid moiety. Particular utilities are to relieve asthma and inflammation in man.

  拮抗温血动物过敏性休克慢反应物质或其成分（如白三烯）的化合物及其中间体和制备方法、药物组合物和给药方法。这些化合物是二苯基羧酸，在单个苯基环和羧酸分子之间具有特殊的连接基团。特别适用于缓解人类的哮喘和炎症。
• US4499299A
  申请人：——

  公开号：US4499299A

  公开（公告）日：1985-02-12
• Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes
  作者：Frederick J. Brown、Peter R. Bernstein、Laura A. Cronk、David L. Dosset、Kevin C. Hebbel、Thomas P. Maduskuie、Howard S. Shapiro、Edward P. Vacek、Ying K. Yee

  DOI：10.1021/jm00124a014

  日期：1989.4

  Considerations of the possible similarities between leukotriene D4 and its prototypical antagonist, FPL 55712, led to the development of a new series of leukotriene antagonists incorporating a hydroxyacetophenone group (e.g., the toluic acids 16 and 18). Although considerable attention has focused on FPL 55712-derived analogues, only limited investigations into alternatives for the standard 4-acetyl-3-hydroxy-2-propylphenoxy moiety have been reported. Therefore, an extensive study of modifications to the hydroxyacetophenone portion of toluic acid 18 was undertaken. Although no viable alternative to the 3-hydroxy moiety was discovered, replacements for the 2-propyl group (34, 37) and the 4-acetyl functionality (56, 59) yielded potent antagonists. A number of compounds exhibited longer duration of action in vivo than FPL 55712.