2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4.4,4-trifluoro-1-butanone | 189956-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4.4,4-trifluoro-1-butanone
• 英文别名: 2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4,4,4-trifluoro-1-butanone；alpha-Methyl-alpha-hydroxy-gamma,gamma,gamma-trifluoro-4'-(methylsulfonyl)butyrophenone；4,4,4-trifluoro-2-hydroxy-2-methyl-1-(4-methylsulfonylphenyl)butan-1-one
• CAS: 189956-23-8
• 化学式: C₁₂H₁₃F₃O₄S
• 分子量: 310.294
• InChiKey: CSCFVJPWMPXALQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4.4,4-trifluoro-1-butanone 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 乙腈 、 苯 为溶剂， 生成 3-Isopropoxy-4-(4-methanesulfonyl-phenyl)-5-methyl-5-(2,2,2-trifluoro-ethyl)-5H-furan-2-one
  参考文献：
  名称：

  Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile

  摘要：

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00739-4
• 作为产物：
  描述：

  alpha-Methyl-alpha-hydroxy-gamma,gamma,gamma-trifluoro-4'-(methylthio)butyrophenone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4.4,4-trifluoro-1-butanone
  参考文献：
  名称：

  Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile

  摘要：

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00739-4

文献信息

• [EN] (METHYLSULFONYL)PHENYL-2-(5H)-FURANONES AS COX-2 INHIBITORS<br/>[FR] (METHYLSULFONYL)PHENYL-2-(5H)-FURANONES EN TANT QU'INHIBITEURS DU COX-2
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1997014691A1

  公开（公告）日：1997-04-24

  (EN) The invention encompasses the novel compound of formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of formula (I).(FR) Cette invention, qui porte sur le nouveau composé répondant à la formule (I), composé s'avérant efficace dans le traitement de maladies liées à la cyclo-oxygénase-2, a également trait à certaines compositions pharmaceutiques qui, contenant des composés de ladite formule (I), servent à traiter lesdites maladies.

  该发明涉及一种新的化合物(I)的使用，该化合物可用于治疗环氧合酶-2介导的疾病。该发明还涉及一些药物组合物，用于治疗环氧合酶-2介导的疾病，其中包括化合物(I)。
• [EN] 3,4-DIARYL-2-HYDROXY-2,5-DIHYDROFURANS AS PRODRUGS TO COX-2 INHIBITORS<br/>[FR] 3,4-DIARYLE-2-HYDROXY-2,5-DIHYDROFURANS UTILISES COMME PROMEDICAMENTS POUR INHIBITEURS DE COX-2
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1997016435A1

  公开（公告）日：1997-05-09

  (EN) The invention encompasses the novel compound of formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of formula (I).(FR) L'invention se rapporte à un nouveau composé de la formule (I) utile dans le traitement de pathologies induites par la cyclooxygénase-2. L'invention se rapporte également à certaines compositions pharmaceutiques destinées au traitement de pathologies induites par la cyclooxygénase-2 et comprenant les composés de la formule (I).

  该发明涵盖了式（I）的新型化合物，可用于治疗环氧合酶-2介导的疾病。该发明还涵盖了某些含有式（I）化合物的药物组合物，用于治疗环氧合酶-2介导的疾病。
• (METHYLSULFONYL)PHENYL-2-(5H)-FURANONES AS COX-2 INHIBITORS
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0863891A1

  公开（公告）日：1998-09-16
• 3,4-DIARYL-2-HYDROXY-2,5-DIHYDROFURANS AS PRODRUGS TO COX-2 INHIBITORS
  申请人：Merck Frosst Canada & Co.

  公开号：EP0904269B1

  公开（公告）日：2002-01-23
• US5698584A
  申请人：——

  公开号：US5698584A

  公开（公告）日：1997-12-16