2-bromo-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone | 183610-69-7

• 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: 2-bromo-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone
• CAS: 183610-69-7
• 化学式: C₁₅H₁₂BrFO₃S
• 分子量: 371.227
• InChiKey: MWSPVZXQINZJFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone 在 10percent Pd/C 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、1.38 MPa 条件下， 反应 18.0h， 生成 3-(4-Fluorophenyl)-7,8-dimethyl-2-(4-methylsulfonylphenyl)imidazo[1,2-b]pyridazine
  参考文献：
  名称：

  Synthesis and SAR of a New Series of COX-2-Selective Inhibitors:  Pyrazolo[1,5-a]pyrimidines

  摘要：

  The synthesis and pharmacological activity of a series of bicyclic pyrazolo[1,5-a]pyrimidines as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vive (carrageenan-induced paw edema and air-pouch model). Modification of the pyrimidine substituents showed that 6,7-disubstitution provided the best activity and led to the identification of 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine (10f) as one of the most potent and selective COX-2 inhibitor in this series.

  DOI：

  10.1021/jm0009383
• 作为产物：
  描述：

  2-(4-fluorophenyl)-1-(4-(methylsulfonyl)phenyl)ethanone 在 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以100%的产率得到2-bromo-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone
  参考文献：
  名称：

  Synthesis and SAR of a New Series of COX-2-Selective Inhibitors:  Pyrazolo[1,5-a]pyrimidines

  摘要：

  The synthesis and pharmacological activity of a series of bicyclic pyrazolo[1,5-a]pyrimidines as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vive (carrageenan-induced paw edema and air-pouch model). Modification of the pyrimidine substituents showed that 6,7-disubstitution provided the best activity and led to the identification of 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine (10f) as one of the most potent and selective COX-2 inhibitor in this series.

  DOI：

  10.1021/jm0009383

文献信息

• Synthesis and biological evaluation of 2,3-diarylthiophenes as selective cox-2 inhibitors. part II: Replacing the heterocycle
  作者：Jacques Yves Gauthier、Yves Leblanc、W. Cameron Black、Chi-Chung Chan、Wanda A. Cromlish、Robert Gordon、Brian P. Kennedey、Cheuk K. Lau、Serge Léger、Zhaoyin Wang、Diane Ethier、Jocelyne Guay、Joseph Mancini、Denis Riendeau、Philip Tagari、Philip Vickers、Elizabeth Wong、Lijing Xu、Peptiboon Prasit

  DOI：10.1016/0960-894x(95)00564-a

  日期：1996.1

  The thiophene ring of DuP 697 was replaced by a variety of heterocycles and the products were tested for their ability to inhibit human Cox-2 and Cox-1, the isozymes of cyclooxygenase.
• IMIDAZO [1,2-a]PYRIDINE DERIVATIVES
  申请人：GLAXO GROUP LIMITED

  公开号：EP0819127A1

  公开（公告）日：1998-01-21
• [EN] IMIDAZO[1,2-a]PYRIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRIDINE IMIDAZO (1,2A)
  申请人：GLAXO GROUP LIMITED

  公开号：WO1996031509A1

  公开（公告）日：1996-10-10

  (EN) The invention provides the compounds of formula (I) and pharmaceutically acceptable derivatives thereof in which: R0 represents halogen; R1 and R2 are independently selected from H, halogen, C1-4alkyl, C1-4alkyl substituted by one or more fluorine atoms, C1-4alkoxy, C1-4hydroxyalkyl, SC1-4alkyl, C(O)H or C(O)C1-4alkyl; and R3 represents C1-4alkyl. Compounds of formula (I) are potent and selective inhibitors of COX-2 and are of use in the treatment of the pain, fever, inflammation of a variety of conditions and diseases.(FR) L'invention décrit des composés de formule (I) et leurs sels pharmaceutiquement acceptables dans laquelle R0 représente halogène; R1 et R2 sont choisis indépendamment parmi H, halogène, C1-4alkyle, C1-4alkyle substitué par un ou plusieurs atomes de fluor, C1-4alkoxy, C1-4hydroxyalkyle, SC1-4alkyle, C(O)H ou C(O)C1-4alkyle; et R3 représente C1-4alkyle. Les composés de formule (I) sont des inhibiteurs puissants et sélectifs de COX-2 et sont utilisés dans le traitement de la douleur, de la fièvre et de l'inflammation dans une variété d'états pathologiques et de maladies.
• Synthesis and SAR of a New Series of COX-2-Selective Inhibitors:  Pyrazolo[1,5-<i>a</i>]pyrimidines
  作者：Carmen Almansa、Alberto F. de Arriba、Fernando L. Cavalcanti、Luis A. Gómez、Agustí Miralles、Manuel Merlos、Julián García-Rafanell、Javier Forn

  DOI：10.1021/jm0009383

  日期：2001.2.1

  The synthesis and pharmacological activity of a series of bicyclic pyrazolo[1,5-a]pyrimidines as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vive (carrageenan-induced paw edema and air-pouch model). Modification of the pyrimidine substituents showed that 6,7-disubstitution provided the best activity and led to the identification of 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine (10f) as one of the most potent and selective COX-2 inhibitor in this series.