2-(2,4-difluorophenoxy)-1-(4-methylsulfanyl)ethanone | 263242-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,4-difluorophenoxy)-1-(4-methylsulfanyl)ethanone
• 英文别名: 2-(2,4-Difluorophenoxy)-1-(4-methylsulfanyl-phenyl)ethanone；2-(2,4-difluorophenoxy)-1-(4-methylsulfanyl phenyl)ethanone；2-(2,4-difluorophenoxy)-1-[4-(methylthio)phenyl]ethanone；2-(2,4-difluorophenoxy)-1-(4-methylsulfanylphenyl)ethanone
• CAS: 263242-00-8
• 化学式: C₁₅H₁₂F₂O₂S
• 分子量: 294.322
• InChiKey: ZHYFMSAURZABER-UHFFFAOYSA-N

物化性质

• 沸点：
  437.3±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,4-difluorophenoxy)-1-(4-methylsulfanyl)ethanone 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以89%的产率得到2-(2,4-difluorophenoxy)-1-(4-methanesulfonylphenyl)ethanone
  参考文献：
  名称：

  2-Phenylpyran-4-one derivatives

  摘要：

  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。

  公开号：

  US20030232880A1
• 作为产物：
  描述：

  2,4-二氟苯酚 、 4-甲基硫代-2-溴苯乙酮 在 monopotassium carbonate 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以72%的产率得到2-(2,4-difluorophenoxy)-1-(4-methylsulfanyl)ethanone
  参考文献：
  名称：

  [EN] 2-PHENYLPYRAN-4-ONE DERIVATIVES AS SELECTIVE COX-2 INHIBITORS
  [FR] DERIVES DE 2-PHENYLPYRAN-4-ONE EN TANT QU'INHIBITEURS DE COX-2 SELECTIFS

  摘要：

  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。

  公开号：

  WO2004072058A1

文献信息

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

  公开号：US20020045644A1

  公开（公告）日：2002-04-18

  2-Phenylpyran-4-one derivatives of formula (I): 1 wherein: R 1 represents an alkyl or —NR 4 R 5 group, wherein R 4 and R 5 each independently represents a hydrogen atom or an alkyl group; R 2 represents an alkyl, C 3 -C 7 cycloalkyl, pyridyl, thienyl, naphthyl, tetrahydronaphthyl or indanyl group, or a phenyl group which may be unsubstituted or substituted by one or more halogen atoms or alkyl, trifluoromethyl, hydroxy, alkoxy, methylthic, amino, mono- or dialkylamino, hydroxalkyl or hydroxycarbonyl groups; R 3 represents a methyl, hydroxymethyl, alkoxymethyl, C 3 -C 7 cycloalkoxymethyl, benzyloxymethyl, hydroxycarbonyl, nitrile, trifluoromethyl or difluoromethyl group or a CH 2 —R 6 group wherein R 6 represents an alkyl group; and X represents a single bond, an oxygen atom, a sulfur atom or a methylene group; or pharmaceutically acceptable salts thereof, processes for their production and synthetic intermediates used in said processes, pharmaceutical compositions containing them and their use in medical treatment.

  化合物公式（I）的2-苯基吡喃-4-酮衍生物：1其中：R1代表烷基或-NR4R5基团，其中R4和R5每个独立地代表氢原子或烷基基团；R2代表烷基，C3-C7环烷基，吡啶基，噻吩基，萘基，四氢萘基或茚基，或苯基，该苯基可以是未取代的或取代了一个或多个卤素原子或烷基，三氟甲基，羟基，烷氧基，甲基硫基，氨基，单烷基或二烷基氨基，羟基烷基或羟基羧基基团；R3代表甲基，羟甲基，烷氧甲基，C3-C7环烷氧甲基，苄氧甲基，羟基羧基，腈基，三氟甲基或二氟甲基基团或CH2-R6基团，其中R6代表烷基基团；X代表单键，氧原子，硫原子或亚甲基基团；或其药学上可接受的盐，用于生产的过程以及用于该过程中使用的合成中间体，包含它们的制药组合物以及它们在医学治疗中的使用。
• 2-Phenylpyran-4-one derivatives as selective cox-2 inhibitors
  申请人：Caturla Javaloyes Francisco Juan

  公开号：US20060142380A1

  公开（公告）日：2006-06-29

  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.

  本发明涉及通式（I）的 2-苯基吡喃-4-衍生物、其制备工艺、含有它们的药物组合物及其医疗用途。
• Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors
  作者：Francisco Caturla、Juan-Miguel Jiménez、Núria Godessart、Mercè Amat、Alvaro Cárdenas、Lídia Soca、Jordi Beleta、Hamish Ryder、María I. Crespo

  DOI：10.1021/jm049882t

  日期：2004.7.1

  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.
• 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.
• 2-PHENYLPYRAN-4-ONE DERIVATIVES
  申请人：Almirall Prodesfarma AG

  公开号：EP1115716B1

  公开（公告）日：2003-01-02