3-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-indole
• 英文别名: 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-1H-indole；3-(4-Fluorophenyl)-2-(4-(methylsulfonyl)-phenyl)indole；2-(4-methylsulfonylphenyl)-3-(4-fluorophenyl)indole；3-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)-1H-indole
• 化学式: C₂₁H₁₆FNO₂S
• 分子量: 365.428
• InChiKey: QQNWTSVELIVSMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(Toluene-4-sulfonylamino)-benzoyl chloride 在 三氯化铝 、 硫酸 、 四氯化钛 、 三乙胺 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 7.75h， 生成 3-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: a new series of selective COX-2 inhibitors

  摘要：

  A new series of substituted 2-sulfonyphenyl-3-phenyl-indole derivatives were synthesized and evaluated for their ability to inhibit COX-2 and COX-lenzymes. Most of the compounds synthesized were found to be highly potent and selective inhibitors of COX-2. This work led to the discovery of 2-aminosulfonylphenyl-3-phenyl-indole 5a which possesses higher activity and selectivity for COX-2 than Celecoxib both in vitro and in vivo. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00046-4

文献信息

• Sulfonyl-containing 2,3-diarylindole compounds, methods for making same, and methods of use thereof
  申请人：——

  公开号：US20040058977A1

  公开（公告）日：2004-03-25

  The present invention relates to sulfonyl-containing 2,3-diarylindole, especially to new compounds of general Formula, to a preparation method for their preparation, to pharmaceutical compositions containing said compound, and to the medical use thereof in the treatment of diseases relating to the inhibition of cyclooxygenase-2 (COX-2).

  本发明涉及含砜基的2,3-二芳基吲哚，特别涉及一般式的新化合物，其制备方法，含有该化合物的药物组合物，以及在治疗与环氧合酶-2（COX-2）抑制有关的疾病中的医疗用途。
• Radiosynthesis of a 18F-labeled 2,3-diarylsubstituted indole via McMurry coupling for functional characterization of cyclooxygenase-2 (COX-2) in vitro and in vivo
  作者：Torsten Kniess、Markus Laube、Ralf Bergmann、Fabian Sehn、Franziska Graf、Joerg Steinbach、Frank Wuest、Jens Pietzsch

  DOI：10.1016/j.bmc.2012.04.022

  日期：2012.6

  The radiosynthesis of 3-(4-[18F]fluorophenyl)-2-(4-methylsulfonylphenyl)-1H-indole [18F]-3 as potential PET radiotracer for functional characterization of cyclooxygenase-2 (COX-2) in vitro and in vivo is described. [18F]-3 was prepared by McMurry cyclization of a 18F-labeled intermediate with low valent titanium and zinc via a two-step procedure in a remote controlled synthesizer unit including HPLC

  放射性合成3-（4- [ 18 F]氟苯基）-2-（4-甲基磺酰基苯基）-1 H-吲哚[ 18 F] -3作为潜在的PET示踪剂，用于表征环氧合酶2（COX-2）的功能。描述了体外和体内。[ 18 F] -3是通过McMurry将18 F标记的含低价钛和锌的中间体通过两步操作在包括HPLC纯化和固相萃取的远程控制合成器单元中环化制备的。以这种方式[ 18 F] - 3在80分钟合成时间合成在10％的总衰变校正收率从[ 18F]氟化物的放射化学纯度> 98％，比活度为74-91 GBq /μmol（EOS）。[ 18 F] -3在体外使用促炎刺激的THP-1和COX-2表达肿瘤细胞系（FaDu，A2058，HT-29）进行了评估，其中放射性示踪剂的摄取与上调的COX- 2表达。[ 18 F] -3的稳定性是通过在大鼠全血和血浆中进行体外孵育以及体内动脉血样品的代谢物分析确定的，显示60分钟后
• Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2
  申请人：Merck Frosst Canada, Inc.

  公开号：US05521213A1

  公开（公告）日：1996-05-28

  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. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  该发明涵盖了公式I的新型化合物，以及一种治疗环氧合酶-2介导疾病的方法，包括向需要此类治疗的患者施用公式I化合物的非毒性治疗有效量。该发明还涵盖了某些用于治疗环氧合酶-2介导疾病的药物组合物，其中包括公式I的化合物。
• 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。
• DIARYL BICYCLIC HETEROCYCLES AS INHIBITORS OF CYCLOOXYGENASE-2
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0778834A1

  公开（公告）日：1997-06-18