4,4-Dimethyl-3-methylene-1-(4-methylsulfonylphenyl)-2-phenyl-1-cyclobutene

• 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: 4,4-Dimethyl-3-methylene-1-(4-methylsulfonylphenyl)-2-phenyl-1-cyclobutene
• 英文别名: 1-(4,4-Dimethyl-3-methylene-2-phenyl-cyclobut-1-enyl)-4-methanesulfonyl-benzene；1-(4,4-dimethyl-3-methylidene-2-phenylcyclobuten-1-yl)-4-methylsulfonylbenzene
• 化学式: C₂₀H₂₀O₂S
• 分子量: 324.444
• InChiKey: FYNBOGBNIRAUMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴茴香硫醚 在 palladium diacetate 2,4,6-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸酐 、 potassium tert-butylate 、 lithium acetate 、 四丁基氯化铵 、 间氯过氧苯甲酸 、 lithium chloride 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成 4,4-Dimethyl-3-methylene-1-(4-methylsulfonylphenyl)-2-phenyl-1-cyclobutene
  参考文献：
  名称：

  Novel 1,2-diarylcyclobutenes: Selective and orally active cox-2 inhibitors

  摘要：

  A series of novel 2,3-diaryl-2-cyclobuten-1-ones have been synthesized and have been evaluated with respect to their ability to inhibit the isozymes of cyclooxygenase, COX-I and COX-2. 4,4-Dimethyl-2-phenyl-3- [4-(methylsulfonyl)phenyl]cyclobutenone 22 was found to be highly selective for inhibition of COX-2 and was orally active (ED(50) = 2.4 mg/kg) in the rat paw edema model. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00501-x

文献信息

• BISARYLCYCLOBUTENE DERIVATES AS CYCLOOXYGENASE INHIBITORS
  申请人：Merck Frosst Canada & Co.

  公开号：EP0889878B1

  公开（公告）日：2002-09-04
• US5817700A
  申请人：——

  公开号：US5817700A

  公开（公告）日：1998-10-06
• [EN] BISARYLCYCLOBUTENE DERIVATES AS CYCLOOXYGENASE INHIBITORS<br/>[FR] DERIVES BISARYLCYCLOBUTENE COMME INHIBITEURS DE LA CYCLO-OXYGENASE
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1997036863A1

  公开（公告）日：1997-10-09

  (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 concerne le nouveau composé de la formule (I), qui est utile pour le traitement des maladies associées à la cyclo-oxygénase-2. L'invention concerne, également, des compositions pharmaceutiques pour le traitement de maladies associées à la cyclo-oxygénase-2 contenant les composés de la formule (I).
• Novel 1,2-diarylcyclobutenes: Selective and orally active cox-2 inhibitors
  作者：Richard W. Friesen、Daniel Dubé、Rejean Fortin、Richard Frenette、Sylvie Prescott、Wanda Cromlish、Gillian M. Greig、Stacia Kargman、Elizabeth Wong、Chi Chung Chan、Robert Gordon、Li Jing Xu、Denis Riendeau

  DOI：10.1016/s0960-894x(96)00501-x

  日期：1996.11

  A series of novel 2,3-diaryl-2-cyclobuten-1-ones have been synthesized and have been evaluated with respect to their ability to inhibit the isozymes of cyclooxygenase, COX-I and COX-2. 4,4-Dimethyl-2-phenyl-3- [4-(methylsulfonyl)phenyl]cyclobutenone 22 was found to be highly selective for inhibition of COX-2 and was orally active (ED(50) = 2.4 mg/kg) in the rat paw edema model. Copyright (C) 1996 Elsevier Science Ltd