[5-(4-Methanesulfonyl-phenyl)-2-methyl-1-(4-trifluoromethyl-phenyl)-1H-pyrrol-3-yl]-oxo-acetic acid ethyl ester | 853055-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [5-(4-Methanesulfonyl-phenyl)-2-methyl-1-(4-trifluoromethyl-phenyl)-1H-pyrrol-3-yl]-oxo-acetic acid ethyl ester
• 英文别名: ethyl 2-[2-methyl-5-(4-methylsulfonylphenyl)-1-[4-(trifluoromethyl)phenyl]pyrrol-3-yl]-2-oxoacetate
• CAS: 853055-05-7
• 化学式: C₂₃H₂₀F₃NO₅S
• 分子量: 479.477
• InChiKey: RZOQNKVXMAFZAI-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C
• 沸点：
  621.8±55.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  90.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [5-(4-Methanesulfonyl-phenyl)-2-methyl-1-(4-trifluoromethyl-phenyl)-1H-pyrrol-3-yl]-oxo-acetic acid ethyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 0.5h， 以70%的产率得到ethyl 2-[1-(2-methyl-5-(4-methylsulphonyl)phenyl)-4-(trifluoromethyl)phenyl-1H-pyrrol-3-yl]acetate
  参考文献：
  名称：

  1,5-Diarylpyrrole-3-acetic Acids and Esters as Novel Classes of Potent and Highly Selective Cyclooxygenase-2 Inhibitors

  摘要：

  A small set of substituted 1,5-diarylpyrrole-3-acetic and -glyoxylic acid derivatives have been synthesized, and their cyclooxygenase (COX-1 and COX-2) inhibiting properties have been evaluated. Some compounds proved to be highly selective COX-2 inhibitors, and their affinity data have been rationalized through docking simulations in terms of interactions with a crystallographic model of the COX-2 binding site.

  DOI：

  10.1021/jm049121q
• 作为产物：
  描述：

  1-[4-(methylsulfonyl)phenyl]pentane-1,4-dione 在 吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 [5-(4-Methanesulfonyl-phenyl)-2-methyl-1-(4-trifluoromethyl-phenyl)-1H-pyrrol-3-yl]-oxo-acetic acid ethyl ester
  参考文献：
  名称：

  1,5-Diarylpyrrole-3-acetic Acids and Esters as Novel Classes of Potent and Highly Selective Cyclooxygenase-2 Inhibitors

  摘要：

  A small set of substituted 1,5-diarylpyrrole-3-acetic and -glyoxylic acid derivatives have been synthesized, and their cyclooxygenase (COX-1 and COX-2) inhibiting properties have been evaluated. Some compounds proved to be highly selective COX-2 inhibitors, and their affinity data have been rationalized through docking simulations in terms of interactions with a crystallographic model of the COX-2 binding site.

  DOI：

  10.1021/jm049121q

文献信息

• 1,5-Diarylpyrrole-3-acetic Acids and Esters as Novel Classes of Potent and Highly Selective Cyclooxygenase-2 Inhibitors
  作者：Mariangela Biava、Giulio Cesare Porretta、Andrea Cappelli、Salvatore Vomero、Fabrizio Manetti、Maurizio Botta、Lidia Sautebin、Antonietta Rossi、Francesco Makovec、Maurizio Anzini

  DOI：10.1021/jm049121q

  日期：2005.5.1

  A small set of substituted 1,5-diarylpyrrole-3-acetic and -glyoxylic acid derivatives have been synthesized, and their cyclooxygenase (COX-1 and COX-2) inhibiting properties have been evaluated. Some compounds proved to be highly selective COX-2 inhibitors, and their affinity data have been rationalized through docking simulations in terms of interactions with a crystallographic model of the COX-2 binding site.