2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one | 190966-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one
• 英文别名: 2-Bromo-3-(4-(methylsulfonyl)phenyl)cyclopent-2-enone；2-bromo-3-(4-methylsulfonylphenyl)cyclopent-2-en-1-one
• CAS: 190966-44-0
• 化学式: C₁₂H₁₁BrO₃S
• 分子量: 315.188
• InChiKey: RWDCKVDOJYLMSM-UHFFFAOYSA-N

物化性质

• 沸点：
  437.0±45.0 °C(Predicted)
• 密度：
  1.617±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(三甲基甲锡烷基)吡啶 、 2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 作用下， 以 various solvent(s) 为溶剂， 生成 2-(2-Pyridinyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  2,3-Diarylcyclopentenones as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors

  摘要：

  Cyclopentenones containing a 4-(methylsulfonyl)phenyl group in the 3-position and a phenyl ring in the 2-position are selective inhibitors of cyclooxygenase-2 (COX-2). The selectivity for COX-2 over COX-1 is dramatically improved by substituting the 2-phenyl group with halogens in the meta position or by replacing the phenyl ring with a 2- or 3-pyridyl ring. Thus the 3,5-difluorophenyl derivative 7 (L1776,967) and the 3-pyridyl derivative 13 (L-784,506) are particularly interesting as potential antiinflammatory agents with reduced side-effect profiles. Both exhibit good oral bioavailability and are potent in standard models of pain, fever, and inflammation yet have a much reduced effect on the GI integrity of rats compared to standard nonsteroidal antiflammatory drugs.

  DOI：

  10.1021/jm980642l
• 作为产物：
  描述：

  3-乙氧基-2-环戊烯酮 在 sodium tungstate 、 正丁基锂 、 硫酸 、 双氧水 、 溴 、 甲基三辛基氯化铵 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  2,3-Diarylcyclopentenones as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors

  摘要：

  Cyclopentenones containing a 4-(methylsulfonyl)phenyl group in the 3-position and a phenyl ring in the 2-position are selective inhibitors of cyclooxygenase-2 (COX-2). The selectivity for COX-2 over COX-1 is dramatically improved by substituting the 2-phenyl group with halogens in the meta position or by replacing the phenyl ring with a 2- or 3-pyridyl ring. Thus the 3,5-difluorophenyl derivative 7 (L1776,967) and the 3-pyridyl derivative 13 (L-784,506) are particularly interesting as potential antiinflammatory agents with reduced side-effect profiles. Both exhibit good oral bioavailability and are potent in standard models of pain, fever, and inflammation yet have a much reduced effect on the GI integrity of rats compared to standard nonsteroidal antiflammatory drugs.

  DOI：

  10.1021/jm980642l

文献信息

• 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.

  这项发明涵盖了化合物I的新颖结构，可用于治疗环氧合酶-2介导的疾病。该发明还涵盖了用于治疗环氧合酶-2介导疾病的某些药物组合物，其中包括化合物I。
• 2-(3,5-difluorophenyl)-3-(4-(methyl-sulfonyl)phenyl)-2-cyclopenten-1-one useful as an inhibitor of cyclooxygenase-2
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0863134A1

  公开（公告）日：1998-09-09

  The invention encompasses the novel compound A, 2-(3,5-difluorophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one, pharmaceutical compositions and use of the compound in the preparation of medicaments for the treatment of cyclooxygenase-2 mediated diseases.

  该发明涵盖了新型化合物A，即2-(3,5-二氟苯基)-3-(4-(甲磺基)苯基)-2-环戊烯-1-酮，以及该化合物在制备用于治疗环氧合酶-2介导的疾病的药物中的应用。
• [EN] PYRIDINYL-2-CYCLOPENTEN-1-ONES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] PYRIDINYL-2-CYCLOPENTEN-1-ONES UTILISEES COMME INHIBITEURS DE CYCLOOXYGENASE SELECTIFS
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1997040012A1

  公开（公告）日：1997-10-30

  (EN) The invention encompasses the novel compound of Formula (I) as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula (I). The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of Formula (I).(FR) L'invention concerne le nouveau composé de la formule (I), ainsi qu'un procédé pour traiter les maladies à médiation par COX-2. Ce procédé consiste à administrer à un patient nécessitant ce type de traitement une quantité thérapeutiquement efficace, non toxique, d'un composé présentant la formule (I). L'invention concerne aussi certaines compositions pharmaceutiques pour le traitement des maladies à médiation par COX-2, comprenant les composés de la formule (I).

  该发明涵盖了化合物I式的新颖化合物，以及治疗COX-2介导疾病的方法，包括向需要这种治疗的患者施用化合物I式的非毒性治疗有效量。该发明还涵盖了用于治疗COX-2介导疾病的某些药物组合物，包括化合物I式。
• [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。
• Pyridinyl-2-cyclopenten-1-ones as selective cyclooxygenase-2 inhibitors
  申请人：Merck Frosst Canada

  公开号：US05922742A1

  公开（公告）日：1999-07-13

  The invention encompasses the novel compound of Formula I as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of Formula I.

  该发明涵盖了化合物I的新型化合物，以及一种治疗COX-2介导的疾病的方法，包括向需要此种治疗的患者施用化合物I的非毒性治疗有效量。 ## STR1 ## 该发明还涵盖了用于治疗COX-2介导的疾病的某些药物组合物，其中包括化合物I。