4-(4-fluorophenyl)-3-phenylfuran-2(5H)-one

• 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: 4-(4-fluorophenyl)-3-phenylfuran-2(5H)-one
• 英文别名: 3-(4-fluorophenyl)-4-phenyl-2H-furan-5-one
• 化学式: C₁₆H₁₁FO₂
• 分子量: 254.261
• InChiKey: IRDHYTJELMYUOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-3-phenylfuran-2(5H)-one 、 sodium thiomethoxide 在 六甲基磷酰三胺 作用下， 反应 1.5h， 生成 4-(4-methylthiophenyl)-3-phenyl-2(5H)-furanone
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING PHENYL HETEROCYCLES AS CYCLOOXYGENASE-2 INHIBITOR
  [FR] PROCEDE DE PREPARATION D'HETEROCYCLES DE PHENYLE UTILISES EN TANT QU'INHIBITEURS DE LA CYCLO-OXYGENASE-2

  摘要：

  本发明涉及一种制备苯基杂环作为环氧合酶-2抑制剂，用于治疗其他环氧合酶介导的疾病的方法，该方法环境友好且具有改进的生产率。更具体地说，本发明涉及一种制备苯基杂环作为环氧合酶-2抑制剂的方法，其特征在于提供一种高纯度的化合物5，具有低生产成本和简单的工艺，不会在制备过程中产生卤素气体，对人体无害且不会对环境造成污染，包括酯内酰化反应，以化合物1为引发剂的取代反应和氧化反应。

  公开号：

  WO2005051935A1
• 作为产物：
  描述：

  [2-(4-Fluorophenyl)-2-oxoethyl] 2-phenylacetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 4-(4-fluorophenyl)-3-phenylfuran-2(5H)-one
  参考文献：
  名称：

  Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors

  摘要：

  We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structureactivity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC(50)s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.

  DOI：

  10.1021/ml500344j

文献信息

• One-Pot Synthesis of 3,4-Diaryl-Substituted 2(5<i>H</i>)-Furanone and Its Commercial Application
  作者：Anil Argade、Jigar Desai、Pravin Thombare、Kiran Shah、Sanjay Gite、Vijay Prajapati、Bipin Pandey、Mukul Jain、Pankaj Patel、Rajesh Bahekar

  DOI：10.1080/00397911.2011.577923

  日期：2012.11

  Abstract One-pot synthesis of 3,4-diaryl substituted 2(5H)-furanones was established and its commercial application has been demonstrated by accomplishing total synthesis of rofecoxib, under mild reaction conditions, with good yields and purity. GRAPHICAL ABSTRACT

  摘要 建立了3,4-二芳基取代的2(5H)-呋喃酮的一锅法合成方法，并通过完成罗非昔布的全合成，在温和的反应条件下，以良好的收率和纯度证明了其商业应用。图形概要
• Gold catalysed reactions with cyclopropenes
  作者：Jürgen T. Bauer、Maximillian S. Hadfield、Ai-Lan Lee

  DOI：10.1039/b815891f

  日期：——

  Gold(I) catalyses the ring-opening addition of cyclopropenes in a mild and regioselective manner.

  金(I)催化温和且区域选择性地促进环丙烯的环打开加成反应。
• Design of Fluorine-Containing 3,4-Diarylfuran-2(5<i>H</i>)-ones as Selective COX-1 Inhibitors
  作者：Md. Jashim Uddin、Anna V. Elleman、Kebreab Ghebreselasie、Cristina K. Daniel、Brenda C. Crews、Kellie D. Nance、Tamanna Huda、Lawrence J. Marnett

  DOI：10.1021/ml500344j

  日期：2014.11.13

  We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structureactivity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC(50)s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.
• [EN] METHOD FOR PREPARING PHENYL HETEROCYCLES AS CYCLOOXYGENASE-2 INHIBITOR<br/>[FR] PROCEDE DE PREPARATION D'HETEROCYCLES DE PHENYLE UTILISES EN TANT QU'INHIBITEURS DE LA CYCLO-OXYGENASE-2
  申请人：IL YANG PHARM CO LTD

  公开号：WO2005051935A1

  公开（公告）日：2005-06-09

  The present invention relates to a method for preparing phenyl heterocycle as cyclooxygenase-2 inhibitor useful in the treatment of other cyclooxygenase meditated diseases, which is environmentally harmonious and has an improved productivity. More particularly, it relates to a method for preparing phenyl heterocycle as cyclooxygenase-2 inhibitor, characterized in providing a high-purity compound of Formula 5 with the low cost of production and a simple process, which is harmless to human and environmental pollution due to not generating a halogen gas when preparing, and comprising the steps of lactonization reaction with a compound of Formula 1 as an initiator; substitution reaction; and oxidation reaction.

  本发明涉及一种制备苯基杂环作为环氧合酶-2抑制剂，用于治疗其他环氧合酶介导的疾病的方法，该方法环境友好且具有改进的生产率。更具体地说，本发明涉及一种制备苯基杂环作为环氧合酶-2抑制剂的方法，其特征在于提供一种高纯度的化合物5，具有低生产成本和简单的工艺，不会在制备过程中产生卤素气体，对人体无害且不会对环境造成污染，包括酯内酰化反应，以化合物1为引发剂的取代反应和氧化反应。