(2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate | 179174-77-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate
• 英文别名: (Z)-2-(4-(Methylsulfonyl)Phenyl)-3-Phenyl-2-Butene-1,4-Diol 1-Acetate；[(Z)-4-hydroxy-2-(4-methylsulfonylphenyl)-3-phenylbut-2-enyl] acetate
• CAS: 179174-77-7
• 化学式: C₁₉H₂₀O₅S
• 分子量: 360.431
• InChiKey: PNZZWJIWQKZHST-HNENSFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 丙酮 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 (2S,3R)-4-Hydroxy-3-(4-methanesulfonyl-phenyl)-2-phenyl-butyric acid
  参考文献：
  名称：

  Synthesis, characterization, and activity of metabolites derived from the cyclooxygenase-2 inhibitor rofecoxib (MK-0966, Vioxx™)

  摘要：

  Metabolites of the COX-2 inhibitor rofecoxib (MK-0966, Vioxx(TM)) were prepared by synthetic or biosynthetic methods. Metabolites include products of oxidation, glucuronidation, reduction and hydrolytic ring opening. Based on an in vitro whole blood assay, none of the known human metabolites of rofecoxib inhibits COX-I nor contributes significantly to the inhibition of COX-2. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00538-2
• 作为产物：
  描述：

  罗非昔布 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate
  参考文献：
  名称：

  Synthesis, characterization, and activity of metabolites derived from the cyclooxygenase-2 inhibitor rofecoxib (MK-0966, Vioxx™)

  摘要：

  Metabolites of the COX-2 inhibitor rofecoxib (MK-0966, Vioxx(TM)) were prepared by synthetic or biosynthetic methods. Metabolites include products of oxidation, glucuronidation, reduction and hydrolytic ring opening. Based on an in vitro whole blood assay, none of the known human metabolites of rofecoxib inhibits COX-I nor contributes significantly to the inhibition of COX-2. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00538-2

文献信息

• Stilbene derivatives useful as cyclooxygenase-2 inhibitors
  申请人：Merck Frosst Canada, Inc.

  公开号：US05849943A1

  公开（公告）日：1998-12-15

  The invention encompasses novel compounds of Formula Iuseful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceuticalcompositions and methods for treatment of cyclooxygenase-2 mediated diseases comprising the use of compounds of Formula I.

  本发明包括用于治疗环氧合酶-2介导疾病的公式I新颖化合物。##STR1## 本发明还包括某些药物组合物和治疗方法，用于治疗包括使用公式I化合物的环氧合酶-2介导疾病。
• [EN] NITRIC OXIDE RELEASING PRODRUGS OF DIARYL-2-(5H)-FURANONES AS CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] PROMEDICAMENTS LIBERANT DE L'OXYDE NITRIQUE DE DIARYL-2-(5H)-FURANONES UTILISES EN TANT QU'INHIBITEURS DE CYCLOOXYGENASE-2
  申请人：MERCK FROSST CANADA INC

  公开号：WO2005070874A1

  公开（公告）日：2005-08-04

  The invention encompasses novel compounds of Formula I, which are nitric oxide-releasing prodrugs of diaryl-2-(5H) furanones useful in the treatment of cyclooxygenase-2 mediated diseases. Formula (I). The invention also encompasses certain pharmaceutical compositions and methods for treating cyclooxygenease-2 mediated diseases comprising the use of compounds of Formula I. The above compounds may be used as a combination therapy with low-dose aspirin to treat chronic cyclooxygenase-2 mediated diseases or conditions while also reducing the risk of thrombotic cardiovascular events.

  该发明涵盖了一种新颖的Formula I化合物，这些化合物是一种硝化氧释放前药，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和治疗环氧合酶-2介导疾病的方法，包括使用Formula I化合物。上述化合物可作为低剂量阿司匹林的联合疗法，用于治疗慢性环氧合酶-2介导的疾病或症状，同时降低血栓性心血管事件的风险。
• Nitric oxide releasing prodrugs of diaryl-2-(5H)-furanones as cyclooxygenase-2 inhibitors
  申请人：——

  公开号：US20040176331A1

  公开（公告）日：2004-09-09

  The invention encompasses novel compounds of Formula I, which are nitric oxide-releasing prodrugs of diaryl-2-(5H) furanones useful in the treatment of cyclooxygenase-2 mediated diseases. 1 The invention also encompasses certain pharmaceutical compositions and methods for treating cyclooxygenase-2 mediated diseases comprising the use of compounds of Formula I. The above compounds may be used as a combination therapy with low-dose aspirin to treat chronic cyclooxygenase-2 mediated diseases or conditions while also reducing the risk of thrombotic cardiovascular events.

  该发明涵盖了一种式I的新颖化合物，这些化合物是对环氧合酶-2介导的疾病治疗中有用的二芳基-2-(5H)呋喃酮的一氧化氮释放前药。该发明还涵盖了某些药物组合和治疗环氧合酶-2介导的疾病的方法，包括使用式I的化合物。上述化合物可用作与低剂量阿司匹林的联合疗法，用于治疗慢性环氧合酶-2介导的疾病或病症，同时减少血栓性心血管事件的风险。
• Nitric Oxide Releasing Prodrugs of Diaryl-2-(5h)-Furanones as Cyclooxygenase-2 Inhibitors
  申请人：Berthelette Carl

  公开号：US20080227758A1

  公开（公告）日：2008-09-18

  The invention encompasses novel compounds of Formula I, which are nitric oxide-releasing prodrugs of diaryl-2-(5H) furanones useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions and methods for treating cyclooxygenase-2 mediated diseases comprising the use of compounds of Formula I. The above compounds may be used as a combination therapy with low-dose aspirin to treat chronic cyclooxygenase-2 mediated diseases or conditions while also reducing the risk of thrombotic cardiovascular events.

  本发明涵盖了一种公式I的新化合物，它们是二芳基-2-(5H)呋喃酮的一氧化氮释放前药，可用于治疗环氧化酶-2介导的疾病。本发明还涵盖了某些药物组合和方法，用于治疗环氧化酶-2介导的疾病，包括使用公式I的化合物。上述化合物可与低剂量阿司匹林联合使用，以治疗慢性环氧化酶-2介导的疾病或病状，同时降低血栓性心血管事件的风险。
• Nitric oxide releasing prodrugs of diaryl-2-(5h)-furanones as cyclooxygenase-2 inhibitors
  申请人：Merck Frosst Canada & Co.

  公开号：US07622502B2

  公开（公告）日：2009-11-24

  The invention encompasses novel compounds of Formula I, which are nitric oxide-releasing prodrugs of diaryl-2-(5H) furanones useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions and methods for treating cyclooxygenase-2 mediated diseases comprising the use of compounds of Formula I. The above compounds may be used as a combination therapy with low-dose aspirin to treat chronic cyclooxygenase-2 mediated diseases or conditions while also reducing the risk of thrombotic cardiovascular events.

  本发明涵盖了I式新化合物，它们是2-(5H)-二苯基呋喃酮的一氧化氮释放前药，可用于治疗环氧合酶-2介导的疾病。本发明还涵盖了某些药物组合和方法，用于治疗环氧合酶-2介导的疾病，包括使用I式化合物。上述化合物可与低剂量阿司匹林联合治疗慢性环氧合酶-2介导的疾病或病况，同时降低血栓性心血管事件的风险。