氟吲哚美辛 | 16401-94-8

• 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
• 中文名称: 氟吲哚美辛
• 英文名称: 2-(1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid
• 英文别名: Fluoroindomethacin；[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid；2-[1-(4-fluorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
• CAS: 16401-94-8
• 化学式: C₁₉H₁₆FNO₄
• 分子量: 341.339
• InChiKey: VSHQGRMCKUHTCA-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C
• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氟吲哚美辛 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 [1-(4-fluorobenzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]acetic acid
  参考文献：
  名称：

  Synthesis of COX-2 and FAAH inhibitors

  摘要：

  描述了制备对COX-2抑制剂有用的吲哚和在这些方法中有用的中间体的方法。

  公开号：

  US20050234244A1
• 作为产物：
  描述：

  5-甲氧基-2-甲基-3-吲哚乙酸 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 trimethyl-tin hydroxide 、 三乙胺 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 氟吲哚美辛
  参考文献：
  名称：

  Straightforward protocol for the efficient synthesis of varied N1-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up

  摘要：

  A library of approximately 40 N-1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2'-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.044

文献信息

• Indolylacetic acid derivatives and preparations containing same for medical treatments
  申请人：GREEN CROSS CORPORATION

  公开号：EP0144845A1

  公开（公告）日：1985-06-19

  Novel indoleacetic acid derivatives and a medical preparation containing such an indoleacetic acid derivative as a major constituent are described. These derivatives are represented by the general formula: wherein all the symbols are as defined in the appended claims. The derivatives are highly soluble in lipid and can be converted into a fat emulsion in any proportion. The medical preparation is useful as an analgesic, for example.

  本文描述了新型吲哚乙酸衍生物和一种以这种吲哚乙酸衍生物为主要成分的医用制剂。 这些衍生物由通式表示： 其中所有符号均如所附权利要求中所定义。 这些衍生物极易溶于脂质，可按任何比例转化为脂肪乳剂。 这种医用制剂可用作镇痛剂等。
• Indoleacetic acid derivative and a pharmaceutical preparation
  申请人：GREEN CROSS CORPORATION

  公开号：EP0179428A2

  公开（公告）日：1986-04-30

  1-(fluoro- or perfluoro lower alkyl-substituted benzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid carboxymethyl ester is found to have antiinflammatory and analgestic activity with less side effects on gastrointestinal traces than its homologue, acemetacin or indometacin.

  研究发现，1-（氟或全氟低级烷基取代的苯甲酰基）-5-甲氧基-2-甲基-1H-吲哚-3-乙酸羧甲酯具有抗炎和镇痛活性，对胃肠道痕迹的副作用小于其同系物醋美辛或吲哚美辛。
• Synthesis and Biological Evaluation of an Indomethacin Library Reveals a New Class of Angiogenesis-Related Kinase Inhibitors
  作者：Claudia Rosenbaum、Patrick Baumhof、Ralf Mazitschek、Oliver Müller、Athanassios Giannis、Herbert Waldmann

  DOI：10.1002/anie.200352582

  日期：2004.1
• Modulation of MRP-1-Mediated Multidrug Resistance by Indomethacin Analogues
  作者：Claudia Rosenbaum、Sonja Röhrs、Oliver Müller、Herbert Waldmann

  DOI：10.1021/jm0499099

  日期：2005.2.1

  Multidrug resistance (MDR) is a major limiting factor in the development and application of drug candidates. MDR caused by MRP-1 is known to be modulated by the nonsteroidal antiinflammatory drug indomethacin. We have synthesized and biologically evaluated a library of indomethacin analogues. The indomethacin-derived compound library was synthesized employing the Fischer-indole synthesis as the key transformation and making use of a "resin-capture-release" strategy. Sixty representative members of the library were evaluated in a cell biological cytotoxicity assay employing the MRP-1 expressing human glioblastoma cell line T98G as a model system. Nine of the 60 tested derivatives increased the doxorubicin-mediated cytotoxicity at a comparable or higher level than indomethacin itself. Analysis of these derivatives revealed an interesting structure-function relationship. Most remarkably, two substances increased the toxicity, when doxorubicin was used at clinically relevant low concentrations, at a higher degree than indomethacin.
• ——
  作者：FUKAYA TSUTOMU、 NAJTO JOTIRO、 XANADA SYUITI、 VATANABEH MASAXIRO、 JOKOYAMA+

  DOI：——

  日期：——