3-(4-Fluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(4-Fluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carbonitrile
• 英文别名: 3-(4-fluorophenyl)sulfanyl-6-methylsulfonyl-1H-indole-2-carbonitrile
• 化学式: C₁₆H₁₁FN₂O₂S₂
• 分子量: 346.406
• InChiKey: OHVHHRUUBCGBLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(4-Fluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester 在 吡啶 、 lithium hydroxide 、 草酰氯 、 氨 、 N,N-二甲基甲酰胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 3-(4-Fluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carbonitrile
  参考文献：
  名称：

  Rational design of 6-methylsulfonylindoles as selective cyclooxygenase-2 inhibitors

  摘要：

  The introduction of 3-arylmethyl, 3-aryloxy and 3-arylthio moieties into a 6-methylsulfonylindole framework using rational drug design led to potent, selective COX-2 inhibitors having efficacy in a rat carrageenan air pouch model. Incorporation of a conformationally more rigid 3-aroyloxy substituent onto the 6-methylsulfonylindole scaffold led to selective, but considerably less potent COX-2 inhibitors. Variation of the hydrophilicity and size of the indole 2-substituent of 3-arylthio-6-methylsulfonylindole inhibitors led to modulation of the COX-2 human whole blood (HWB) potency and selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.075

文献信息

• Indole derivatives as anti-inflammatory agents
  申请人：——

  公开号：US20030130337A1

  公开（公告）日：2003-07-10

  This invention relates to compounds, which are generally anti-inflammatory and analgesic compounds, and which are represented by Formula I: 1 wherein A is a —CH 2 —, —O—, —S—, or —S(O)—; and the other substituents are as defined in the specification; or individual isomers, mixtures of isomers, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds and methods for their use as therapeutic agents

  本发明涉及一类化合物，通常为抗炎和镇痛化合物，其由以下式I表示：其中A为—CH2—、—O—、—S—或—S(O)—；其他取代基如规范中定义；或其个别异构体、异构体混合物和其药用可接受盐。该发明还涉及含有这类化合物的药物组合物以及它们作为治疗剂的使用方法。
• [EN] INDOLE DERIVATIVES AS COX II INHIBITORS<br/>[FR] DERIVES D'INDOLE UTILES COMME INHIBITEURS DE COX II
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003029212A1

  公开（公告）日：2003-04-10

  This present invention relates to indole derivatives of Formula (I); wherein A, Ar and R1 to R4 are as defines in the specification. The compounds are useful as a selective COX-II inhibitor and, therefore, may be used for the treatment of COX-II mediated diseases.

  本发明涉及公式（I）中的吲哚衍生物；其中A、Ar和R1至R4如规范中所定义。这些化合物可用作选择性COX-II抑制剂，因此可用于治疗COX-II介导的疾病。
• INDOLE DERIVATIVES AS COX II INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1438289A1

  公开（公告）日：2004-07-21
• US6872744B2
  申请人：——

  公开号：US6872744B2

  公开（公告）日：2005-03-29
• US7074939B2
  申请人：——

  公开号：US7074939B2

  公开（公告）日：2006-07-11