3-Hydroxy-5-methyl-4-(4-methylsulfonylphenyl)-5-(2,2,2-trifluoroethyl)furan-2-one | 190966-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Hydroxy-5-methyl-4-(4-methylsulfonylphenyl)-5-(2,2,2-trifluoroethyl)furan-2-one
• 英文别名: 3-hydroxy-5-methyl-4-(4-methylsulfonylphenyl)-5-(2,2,2-trifluoroethyl)furan-2-one
• CAS: 190966-57-5
• 化学式: C₁₄H₁₃F₃O₅S
• 分子量: 350.315
• InChiKey: IIWRLXZRDFRRHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-碘代丙烷 、 3-Hydroxy-5-methyl-4-(4-methylsulfonylphenyl)-5-(2,2,2-trifluoroethyl)furan-2-one 在 silver carbonate 作用下， 以 苯 为溶剂， 生成 3-Isopropoxy-4-(4-methanesulfonyl-phenyl)-5-methyl-5-(2,2,2-trifluoro-ethyl)-5H-furan-2-one
  参考文献：
  名称：

  Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile

  摘要：

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00739-4
• 作为产物：
  描述：

  2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4.4,4-trifluoro-1-butanone 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 3-Hydroxy-5-methyl-4-(4-methylsulfonylphenyl)-5-(2,2,2-trifluoroethyl)furan-2-one
  参考文献：
  名称：

  Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile

  摘要：

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00739-4

文献信息

• Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile
  作者：Yves Leblanc、Patrick Roy、Zhaoyin Wang、Chun Sing Li、Nathalie Chauret、Deborah A. Nicoll-Griffith、José M. Silva、Yves Aubin、James A. Yergey、Chi Chung Chan、Denis Riendeau、Christine Brideau、Robert Gordon、Lijing Xu、Janine Webb、Denise M. Visco、Petpiboon Prasit

  DOI：10.1016/s0960-894x(02)00739-4

  日期：2002.11

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.