ethyl 4-{[(2S)-2-ethyl-6-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate | 888203-34-7

• 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: ethyl 4-{[(2S)-2-ethyl-6-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate
• CAS: 888203-34-7
• 化学式: C₁₉H₁₉FN₂O₆S
• 分子量: 422.434
• InChiKey: DSMQYIGUVHAMEL-INIZCTEOSA-N

物化性质

• 熔点：
  133-136 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-{[(2S)-2-ethyl-6-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate 在 sodium hydroxide 、 caesium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 4.5h， 生成 (3S)-3-ethyl-7-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one
  参考文献：
  名称：

  Synthesis and activity of a new class of pathway-selective estrogen receptor ligands: Hydroxybenzoyl-3,4-dihydroquinoxalin-2(1H)-ones

  摘要：

  The anti-inflammatory activity of non-selective estrogens has been attributed to their ability to antagonize the activity of nuclear factor KB (NF-kappa B), a known mediator of inflammatory responses. Here we report the identification of a potent new class of pathway-selective ER ligands that selectively antagonize NF-kappa B functional activity, while exhibiting a lack of classical estrogenic effect. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.001
• 作为产物：
  描述：

  (2S)-2-[(4-fluoro-2-nitrophenyl)amino]butanoic acid 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.74 kPa 条件下， 反应 15.5h， 生成 ethyl 4-{[(2S)-2-ethyl-6-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate
  参考文献：
  名称：

  Synthesis and activity of a new class of pathway-selective estrogen receptor ligands: Hydroxybenzoyl-3,4-dihydroquinoxalin-2(1H)-ones

  摘要：

  The anti-inflammatory activity of non-selective estrogens has been attributed to their ability to antagonize the activity of nuclear factor KB (NF-kappa B), a known mediator of inflammatory responses. Here we report the identification of a potent new class of pathway-selective ER ligands that selectively antagonize NF-kappa B functional activity, while exhibiting a lack of classical estrogenic effect. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.001