3-(2-fluorophenyl)-5-methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one

• 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: 3-(2-fluorophenyl)-5-methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one
• 英文别名: 3-(4-Fluorophenyl)-5-methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone；3-(4-Fluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-methoxy-5-methyl-5H-furan-2-one；3-(4-fluorophenyl)-5-methoxy-5-methyl-4-(4-methylsulfonylphenyl)furan-2-one
• 化学式: C₁₉H₁₇FO₅S
• 分子量: 376.405
• InChiKey: PBJWWPFSOCFQEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-bromo-1-(4-(methylsulfonyl)phenyl)-propan-1-one 在 air 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 3-(2-fluorophenyl)-5-methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one
  参考文献：
  名称：

  3,4-Diaryl-5-hydroxyfuranones: highly selective inhibitors of cyclooxygenase-2 with aqueous solubility

  摘要：

  The introduction of a hydroxyl group into the 5-position of the diaryl furanone system provides highly selective inhibitors of cyclooxygenase-2. These molecules can be converted into their sodium salts which are water soluble, facilitating intravenous formulation. These salts show excellent potency in rat models of pain, fever and inflammation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00046-5

文献信息

• [EN] DIARYL-5-OXYGENATED-2-(5H)-FURANONES AS COX-2 INHIBITORS<br/>[FR] DIARYL-5-OXYGENE-2-(5H)-FURANONES UTILES COMME INHIBITEURS DE COX-2
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1996036623A1

  公开（公告）日：1996-11-21

  (EN) The invention encompasses the novel compound of Formula (I) as well as a method of treating cyclooxygenase-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 cyclooxygenase-2 mediated diseases comprising compounds of Formula (I).(FR) L'invention concerne le nouveau composé de formule (I) ainsi qu'un procédé de traitement de maladies induites par cyclooxygénase-2, consistant à administrer à un patient ayant besoin d'un tel traitement une quantité non toxique, thérapeutiquement efficace d'un composé de formule (I). L'invention concerne également certaines compositions pharmaceutiques permettant de traiter les maladies induites par cyclooxygénase-2, ces compositions comprenant des composés de la formule (I).

  该发明涵盖了化合物I的新颖化合物，以及治疗环氧合酶-2介导的疾病的方法，包括向需要此类治疗的患者施用化合物I的非毒性治疗有效量。该发明还涵盖了用于治疗环氧合酶-2介导的疾病的某些药物组合物，其中包括化合物I。
• Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones
  作者：Gai-Zhi Liu、Hai-Wei Xu、Peng Wang、Zong-Tao Lin、Ying-Chao Duan、Jia-Xin Zheng、Hong-Min Liu

  DOI：10.1016/j.ejmech.2013.04.062

  日期：2013.7

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.
• DIARYL-5-OXYGENATED-2-(5H)-FURANONES AS COX-2 INHIBITORS
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0828724A1

  公开（公告）日：1998-03-18
• US5691374A
  申请人：——

  公开号：US5691374A

  公开（公告）日：1997-11-25
• 3,4-Diaryl-5-hydroxyfuranones: highly selective inhibitors of cyclooxygenase-2 with aqueous solubility
  作者：W.Cameron Black、Christine Brideau、Chi-Chung Chan、Stella Charleson、Wanda Cromlish、Robert Gordon、Erich L. Grimm、Gregory Hughes、Serge Leger、Chun-Sing Li、Denis Riendeau、Michel Thérien、Zhaoyin Wang、Li-Jing Xu、Petpiboon Prasit

  DOI：10.1016/s0960-894x(03)00046-5

  日期：2003.3

  The introduction of a hydroxyl group into the 5-position of the diaryl furanone system provides highly selective inhibitors of cyclooxygenase-2. These molecules can be converted into their sodium salts which are water soluble, facilitating intravenous formulation. These salts show excellent potency in rat models of pain, fever and inflammation. (C) 2003 Elsevier Science Ltd. All rights reserved.