3-(4-bromo-2-fluorophenoxy)-6-methyl-2-[4-(methylthio)phenyl]-4H-pyran-4-one | 746624-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-bromo-2-fluorophenoxy)-6-methyl-2-[4-(methylthio)phenyl]-4H-pyran-4-one
• 英文别名: 3-(4-Bromo-2-fluorophenoxy)-6-methyl-2-(4-methylsulfanylphenyl)pyran-4-one
• CAS: 746624-42-0
• 化学式: C₁₉H₁₄BrFO₃S
• 分子量: 421.287
• InChiKey: CJLWFDMKAPPRGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-bromo-2-fluorophenoxy)-6-methyl-2-[4-(methylthio)phenyl]-4H-pyran-4-one 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3-(4-Bromo-2-fluoro-phenoxy)-2-[4-((R)-methanesulfinyl)-phenyl]-6-methyl-pyran-4-one
  参考文献：
  名称：

  Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors

  摘要：

  The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives I and 3, after oral administration to rats. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.101
• 作为产物：
  描述：

  乙酸酐 、 2-(4-bromo-2-fluorophenoxy)-1-(4-methylsulfanylphenyl)ethanone 在 PPA 作用下， 生成 3-(4-bromo-2-fluorophenoxy)-6-methyl-2-[4-(methylthio)phenyl]-4H-pyran-4-one
  参考文献：
  名称：

  Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors

  摘要：

  The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives I and 3, after oral administration to rats. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.101

文献信息

• [EN] 2-PHENYLPYRAN-4-ONE DERIVATIVES AS SELECTIVE COX-2 INHIBITORS<br/>[FR] DERIVES DE 2-PHENYLPYRAN-4-ONE EN TANT QU'INHIBITEURS DE COX-2 SELECTIFS
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2004072058A1

  公开（公告）日：2004-08-26

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

  本发明涉及一般式（I）的2-苯基吡喃-4-衍生物及其制备方法，含有它们的药物组合物以及它们的医药用途。
• 2-PHENYLPYRAN-4-ONE DERIVATIVES AS SELECTIVE COX-2 INHIBITORS
  申请人：Almirall Prodesfarma, S.A.

  公开号：EP1592680A1

  公开（公告）日：2005-11-09
• US7582676B2
  申请人：——

  公开号：US7582676B2

  公开（公告）日：2009-09-01
• Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors
  作者：Francisco Caturla、Mercè Amat、Raquel F. Reinoso、Elena Calaf、Graham Warrellow

  DOI：10.1016/j.bmcl.2006.03.101

  日期：2006.7

  The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives I and 3, after oral administration to rats. (c) 2006 Elsevier Ltd. All rights reserved.