2-(4-bromo-2-pyridinyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one

• 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-(4-bromo-2-pyridinyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one
• 英文别名: 2-(5-Bromo-2-pyridinyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one；2-(5-bromopyridin-2-yl)-3-(4-methylsulfonylphenyl)cyclopent-2-en-1-one
• 化学式: C₁₇H₁₄BrNO₃S
• 分子量: 392.273
• InChiKey: QMGHPAHRSSMDDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙氧基-2-环戊烯酮 在 sodium tungstate 、 正丁基锂 、 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 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 23.5h， 生成 2-(4-bromo-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

文献信息

• [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。
• 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。
• PYRIDINYL-2-CYCLOPENTEN-1-ONES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0900201A1

  公开（公告）日：1999-03-10
• US5922742A
  申请人：——

  公开号：US5922742A

  公开（公告）日：1999-07-13
• 2,3-Diarylcyclopentenones as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors
  作者：W. Cameron Black、Christine Brideau、Chi-Chung Chan、Stella Charleson、Nathalie Chauret、David Claveau、Diane Ethier、Robert Gordon、Gillian Greig、Jocelyne Guay、Gregory Hughes、Paule Jolicoeur、Yves Leblanc、Deborah Nicoll-Griffith、Nathalie Ouimet、Denis Riendeau、Denise Visco、Zhaoyin Wang、Lijing Xu、Petpiboon Prasit

  DOI：10.1021/jm980642l

  日期：1999.4.1

  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.