3-(4-fluoro-2-methylphenoxy)-2-(4-methanesulfonylphenyl)-6-methylpyran-4-one | 361381-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-fluoro-2-methylphenoxy)-2-(4-methanesulfonylphenyl)-6-methylpyran-4-one
• 英文别名: 3-(4-Fluoro-2-methyl-phenoxy)-2-(4-methanesulfonyl-phenyl)-6-methyl-pyran-4-one；3-(4-fluoro-2-methylphenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one
• CAS: 361381-10-4
• 化学式: C₂₀H₁₇FO₅S
• 分子量: 388.416
• InChiKey: OETIMMSWPHDTTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氟-2-甲基苯酚 在 Oxone 、 PPA 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 3-(4-fluoro-2-methylphenoxy)-2-(4-methanesulfonylphenyl)-6-methylpyran-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors

  摘要：

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.

  DOI：

  10.1021/jm049882t

文献信息

• 2-Phenylpyran-4-one derivatives
  申请人：——

  公开号：US20030232880A1

  公开（公告）日：2003-12-18

  The present invention relates to 2-(4-sulphonylphenyl)pyran-4-one derivatives of general formula 1 processes for their preparation, pharmaceutical compositions containing them, and their medical uses.

  本发明涉及通式为1的2-(4-磺酰基苯基)吡喃-4-酮衍生物的制备方法、含有它们的制药组合物以及它们的医药用途。
• 2-PHENYLPYRAN-4-ONE DERIVATIVES
  申请人：Almirall Prodesfarma AG

  公开号：EP1263751A1

  公开（公告）日：2002-12-11
• US7354936B2
  申请人：——

  公开号：US7354936B2

  公开（公告）日：2008-04-08
• [EN] 2-PHENYLPYRAN-4-ONE DERIVATIVES<br/>[FR] DERIVES DE 2-PHENYLPYRAN-4-ONE
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2001068633A1

  公开（公告）日：2001-09-20

  The present invention relates to 2-(4-sulphonylphenyl)pyran-4-one derivatives of general formula (I), processes for their preparation, pharmaceutical compositions containing them, and their medical uses.