(S)-2-hydroxy-2-methyl-1-[4-(methylsulfonyl)phenyl]butan-1-one | 189956-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-hydroxy-2-methyl-1-[4-(methylsulfonyl)phenyl]butan-1-one
• 英文别名: (S)-2-Hydroxy-2-methyl-1-(4-methylsulfonylphenyl)-butan-1-one；(2S)-2-hydroxy-2-methyl-1-(4-methylsulfonylphenyl)butan-1-one
• CAS: 189956-13-6
• 化学式: C₁₂H₁₆O₄S
• 分子量: 256.323
• InChiKey: OJHHGIUBBKWEBK-LBPRGKRZSA-N

物化性质

• 沸点：
  448.2±41.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxy-2-methyl-1-[4-(methylsulfonyl)phenyl]butan-1-one 在 三氟乙酸异丙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 (S)-5-ethyl-5-methyl-3-(1-methylethoxy)-4-[(4-methylsulfonyl)phenyl]-3-oxolen-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：

  (1R,2S)-1-(1-ethoxyethoxy)-2-methyl-1-(4-methylsulfonylphenyl)butan-2-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 (S)-2-hydroxy-2-methyl-1-[4-(methylsulfonyl)phenyl]butan-1-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

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。
• 3,4-diaryl-2-hydroxy-2,5-dihydrofurans as prodrugs to COX-2 inhibitors
  申请人：Merck Frosst Canada, Inc.

  公开号：US05698584A1

  公开（公告）日：1997-12-16

  The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  本发明涵盖了公式I的新化合物，可用于治疗环氧合酶-2介导的疾病。 ## STR1 ## 本发明还涵盖了某些包含公式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：US06020343A1

  公开（公告）日：2000-02-01

  The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  该发明涵盖了公式I的新化合物，可用于治疗环氧合酶-2介导的疾病。 ##STR1## 该发明还涵盖了某些药物组合物，用于治疗环氧合酶-2介导的疾病，其中包括公式I的化合物。
• 3,4-Diaryl-2-hydroxy-2,5-dihydrofurans as prodrugs to cox-2 inhibitors
  申请人：Merck Frosst Canada & Co.

  公开号：US06057319A1

  公开（公告）日：2000-05-02

  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). ##STR1##

  这项发明涵盖了公式（I）的新化合物，可用于治疗环氧合酶-2介导的疾病。该发明还涵盖了某些药物组合物，用于治疗环氧合酶-2介导的疾病，其中包括公式（I）的化合物。##STR1##