3-(4-Methanesulfonyl-phenyl)-2-phenyl-1,2-dihydro-quinoxaline | 699003-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(4-Methanesulfonyl-phenyl)-2-phenyl-1,2-dihydro-quinoxaline
• 英文别名: 3-(4-Methylsulfonylphenyl)-2-phenyl-1,2-dihydroquinoxaline
• CAS: 699003-35-5
• 化学式: C₂₁H₁₈N₂O₂S
• 分子量: 362.452
• InChiKey: MDOLXLOKMOALAC-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250 °C
• 沸点：
  581.8±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-(4-Methanesulfonyl-phenyl)-2-phenyl-1,2-dihydro-quinoxaline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到(2RS)-1-[3-(4-methylsulfonylphenyl)-2-phenyl-1,2-dihydro-1-quinoxalinyl]-1-ethanone
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

  摘要：

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.033
• 作为产物：
  描述：

  茴香硫醚 在 三氯化铝 、 氢溴酸 、 双氧水 、 溴 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-(4-Methanesulfonyl-phenyl)-2-phenyl-1,2-dihydro-quinoxaline
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

  摘要：

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.033