2-[4-(aminosulfonyl)phenyl]-1-(4-fluorophenyl)ethanone | 185345-82-8

• 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-[4-(aminosulfonyl)phenyl]-1-(4-fluorophenyl)ethanone
• 英文别名: 4-[2-(4-fluorophenyl)-2-oxoethyl]-1-benzenesulfonamide；2-(4-aminosulfonylphenyl)-1-(4-fluorophenyl)ethanone；4-[2-(4-Fluorophenyl)-2-oxoethyl]benzenesulfonamide
• CAS: 185345-82-8
• 化学式: C₁₄H₁₂FNO₃S
• 分子量: 293.319
• InChiKey: LLRYEJYYLTWDCT-UHFFFAOYSA-N

物化性质

• 沸点：
  492.3±55.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-(aminosulfonyl)phenyl]-1-(4-fluorophenyl)ethanone 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 4-[2-(4-fluorophenyl)-2-oxoacetyl]-1-benzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

  摘要：

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.033
• 作为产物：
  描述：

  3'-氟-2-苯基苯乙酮 生成 2-[4-(aminosulfonyl)phenyl]-1-(4-fluorophenyl)ethanone
  参考文献：
  名称：

  SUBSTITUTED IMIDAZO[1,2A]AZINES AS SELECTIVE INHIBITORS OF COX-2

  摘要：

  公开号：

  EP1104762B1

文献信息

• 2,3-Diaryl-substituted indole based COX-2 inhibitors as leads for imaging tracer development
  作者：Markus Laube、Christoph Tondera、Sai Kiran Sharma、Nicole Bechmann、Franz-Jacob Pietzsch、Arne Pigorsch、Martin Köckerling、Frank Wuest、Jens Pietzsch、Torsten Kniess

  DOI：10.1039/c4ra05650g

  日期：——

  A series of 2,3-diaryl-substituted indoles containing a fluorine or methoxy group was synthesized via Fischer indole synthesis, McMurry cyclization, or Bischler–Möhlau reaction to identify potential leads for PET radiotracer development.

  一系列含有氟或甲氧基的2,3-二芳基取代吲哚化合物通过菲舍尔吲哚合成、麦克默里环化反应或比希勒-默劳反应合成，以寻找正电子发射断层扫描（PET）放射性示踪剂开发的潜在先导化合物。
• Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors
  申请人：G.D. Searle & Co.

  公开号：US20040147565A1

  公开（公告）日：2004-07-29

  This invention is in the field of antiinflammatory pharmaceutical agents and specifically relates to compounds, compositions and methods for treating disorders mediated by cyclooxygenase-2 or 5-lipoxygenase, such as inflammation.

  这项发明涉及抗炎药物领域，具体涉及化合物、组合物和治疗通过环氧合酶-2或5-脂氧合酶介导的疾病（如炎症）的方法。
• [EN] SUBSTITUTED OXAZOLES FOR THE TREATMENT OF INFLAMMATION<br/>[FR] OXAZOLES SUBSTITUES UTILISES DANS LE TRAITEMENT D'INFLAMMATIONS
  申请人：G.D. SEARLE & CO.

  公开号：WO1996036617A1

  公开（公告）日：1996-11-21

  (EN) A class of substituted oxazoles is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by formula (I), wherein R is selected from hydrido, halo, mercapto, hydroxyl, carboxyalkylthio, carboxyalkylthioalkyl, carboxyalkoxy, carboxyalkoxyalkyl, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy, aryloxy, aralkoxy, alkylamino, aminocarbonyl, alkoxyalkyl, carboxy(haloalkyl), alkyl, hydroxyalkyl, haloalkyl, alkenyl, hydroxyalkenyl, alkynyl, hydroxyalkynyl, cycloalkyl, cycloalkylalkyl, aminoalkyl, hydroxyalkoxyalkyl, alkylcarbonyl, phosphonylalkyl, amino acid residue, heterocyclylalkyl, cyanoalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxy, carboxyalkyl, arylthioalkyl, aminocarbonylalkyl, alkylcarbonylaminoalkyl, alkoxycarbonylaminoalkyl, aralkoxycarbonylaminoalkyl, aryl, heteroaryl, aralkyl, aryloxyalkyl, aralkoxyalkyl, heteroaryloxyalkyl and heteroarylalkoxyalkyl; wherein R1 is selected from cycloalkyl, cycloalkenyl, aryl and heterocyclyl, wherein R1 is optionally substituted at a substitutable position by alkyl, alkylamino, alkoxy and halo; wherein R2 is selected from alkyl and amino; and wherein R3 is selected from hydrido and alkyl.(FR) L'invention se rapporte à une classe d'oxazoles substitués destinés à être utilisés dans le traitement d'inflammations ou de troubles liés à des inflammations. Des composés d'intérêt particulier sont définis par la formule (I) dans laquelle R est sélectionné parmi hydrido, halo, mercapto, hydroxyle, carboxyalkylthio, carboxyalkylthioalkyle, carboxyalcoxy, carboxyalcoxyalkyle, haloalcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, alcoxy, aryloxy, aralcoxy, alkylamino, aminocarbonyle, alcoxyalkyle, carboxy(haloalkyle), alkyle, hydroxyalkyle, haloalkyle, alcényle, hydroxyalcényle, alkynyle, hydroxyalkynyle, cycloalkyle, cycloalkylalkyle, aminoalkyle, hydroxyalcoxyalkyle, alkylcarbonyle, phosphonylalkyle, un résidu aminoacide, hétérocyclylalkyle, cyanoalkyle, alcoxycarbonyle, alcoxycarbonylalkyle, carboxy, carboxyalkyle, arylthioalkyle, aminocarbonylalkyle, alkylcarbonylaminoalkyle, alcoxycarbonylaminoalkyle, aralcoxycarbonylaminoalkyle, aryle, hétéroaryle, aralkyle, aryloxyalkyle, aralcoxyalkyle, hétéroaryloxyalkyle et hétéroarylalcoxyalkyle; où R1 est sélectionné parmi cycloalkyle, cycloalcényle, aryle et hétérocyclyle, R1 étant éventuellement substitué à une position substituable par alkyle, alkylamino, alcoxy et halo; où R2 est sélectionné parmi alkyle et amino; et où R3 est sélectionné parmi hydrido et alkyle.

  (中文) 描述了一类替代噁唑用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由公式（I）定义，其中R从氢化物，卤素，巯基，羟基，羧基烷基硫，羧基烷基硫烷基，羧基烷氧基，羧基烷氧基烷基，卤代烷氧基，烷基硫，烷基亚磺酰基，烷氧基，芳氧基，芳基氧烷基，烷基氨基，氨基羰基，烷氧基烷基，羧基（卤代烷基），烷基，羟基烷基，卤代烷基，烯基，羟基烯基，炔基，羟基炔基，环烷基，环烷基烷基，氨基烷基，羟基烷氧基烷基，烷基羰基，磷酸酯基烷基，氨基酸残基，杂环烷基烷基，氰基烷基，烷氧羰基，烷氧羰基烷基，羧基，羧基烷基，芳基硫烷基，氨基羰基烷基，烷基羰基氨基烷基，烷氧羰基氨基烷基，芳基氧羰基氨基烷基，芳基，杂环芳基，芳基氧烷基，芳基氧烷基烷基，杂环芳基氧烷基和杂环芳基氧烷基烷基中选择; 其中R1从环烷基，环烯基，芳基和杂环烷基中选择，其中R1在可替换位置上可选地被烷基，烷基氨基，烷氧基和卤素取代; 其中R2从烷基和氨基中选择; 而R3从氢化物和烷基中选择。
• SUBSTITUTED IMIDAZO 1,2A]AZINES AS SELECTIVE INHIBOTORS OF COX-2
  申请人：LABORATORIOS S.A.L.V.A.T., S.A.

  公开号：EP1104762A1

  公开（公告）日：2001-06-06

  The invention refers to new compounds of formula (I), wherein A and B are selected from the group consisting of N and CH, with the condition that when A is N, B is N; R1 is selected from the group consisting of CH3 and NH2; R2 and R3 are selected from the group consisting of H, CH3, Br, Cl, COCH3 and OCH3; and R4, R5 and R6, are selected from the group consisting of H, F, Cl, Br, (C1-C3)-alkyl, trifluoromethyl, (C1-C3)-alkoxy and trifluoromethoxy. Compounds of formula (I) are prepared by reaction of a substituted aminoazine with a substituted 2-bromo-2-(4-R1-sulfonylphenyl)-1-phenylethanone in a polar solvent. These new compounds inhibit COX-2 with high selectivity over COX-1. They are useful for the treatment of inflamation and/or cyclooxygenase-mediated diseases, having the additional advantage of a reduced potencial for ulcerogenic effects.

  本发明涉及式(I)的新化合物，其中A和B选自由N和CH组成的组，条件是当A为N时，B为N；R1选自由CH3和NH2组成的组；R2和R3选自由H、CH3、Br、Cl、COCH3和OCH3组成的组；以及R4、R5和R6选自由H、F、Cl、Br、(C1-C3)-烷基、三氟甲基、(C1-C3)-烷氧基和三氟甲氧基组成的组。式(I)化合物是由取代的氨基嗪与取代的 2-溴-2-(4-R1-砜基苯基)-1-苯乙酮在极性溶剂中反应制备而成。这些新化合物抑制 COX-2 的选择性高于 COX-1。它们可用于治疗炎症和/或环氧合酶介导的疾病，还具有减少致溃疡作用的潜力。
• 1,2-Diaryl-1-ethanone and pyrazolo [4,3-c] quinoline-4-one as novel selective cyclooxygenase-2 inhibitors
  作者：Bipul Baruah、Kavitha Dasu、Balasubramanian Vaitilingam、Akhila Vanguri、Seshagiri Rao Casturi、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.bmcl.2003.10.052

  日期：2004.1

  Novel 1,2-diaryl-1-ethanone I and pyrazolo [4,3-c] quinoline-4-one 2, with pharmacophores different from the known COX inhibitors were identified as selective COX-2 inhibitors. The communication briefly describes SAR of both the series. (C) 2003 Elsevier Ltd. All rights reserved.