1-(4-methylphenyl)-2-(2-nitrophenoxy)ethanone | 74413-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methylphenyl)-2-(2-nitrophenoxy)ethanone
• 英文别名: 2-(2-nitro-phenoxy)-1-p-tolyl-ethanone；2-(2-Nitro-phenoxy)-1-p-tolyl-aethanon
• CAS: 74413-00-6
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: ZOZNJDCPVUFTMM-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C(Solvent: Ethanol)
• 沸点：
  457.9±30.0 °C(predicted)
• 密度：
  1.247±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methylphenyl)-2-(2-nitrophenoxy)ethanone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0~140.0 ℃ 、405.33 kPa 条件下， 反应 3.0h， 生成 ethyl 3,7-dihydro-7-oxo-3-(4-methylphenyl)-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate
  参考文献：
  名称：

  7-Oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamides as Selective CB₂ Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists

  摘要：

  Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB(2) K-i = 2.5 nM, SI = 166; 21, hCB(2) K-i = 0.81 nM, SI = 383; 38, hCB(2) K-i = 15.8 nM, SI > 633; 56, hCB(2) K-i = 8.12 nM, SI > 1231; (R)-58, hCB(2) K-i = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.

  DOI：

  10.1021/jm300763w
• 作为产物：
  描述：

  硝苯酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以73%的产率得到1-(4-methylphenyl)-2-(2-nitrophenoxy)ethanone
  参考文献：
  名称：

  7-Oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamides as Selective CB₂ Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists

  摘要：

  Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB(2) K-i = 2.5 nM, SI = 166; 21, hCB(2) K-i = 0.81 nM, SI = 383; 38, hCB(2) K-i = 15.8 nM, SI > 633; 56, hCB(2) K-i = 8.12 nM, SI > 1231; (R)-58, hCB(2) K-i = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.

  DOI：

  10.1021/jm300763w

文献信息

• Kunckell, Chemisches Zentralblatt, 1913, p. I, 1768
  作者：Kunckell

  DOI：——

  日期：——
• Kunckell, Berichte der Deutschen Pharmazeutischen Gesellschaft, vol. 23, p. 275
  作者：Kunckell

  DOI：——

  日期：——
• Kunckell, Berichte der Deutschen Pharmazeutischen Gesellschaft, vol. 23, p. 276
  作者：Kunckell

  DOI：——

  日期：——
• BATTISTONI P.; BRUNI P.; FAVA G., TETRAHEDRON, 1979, 35, NO 14. 1771-1775
  作者：BATTISTONI P.、 BRUNI P.、 FAVA G.

  DOI：——

  日期：——
• 7-Oxo-[1,4]oxazino[2,3,4-<i>ij</i>]quinoline-6-carboxamides as Selective CB₂ Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists
  作者：Pier Giovanni Baraldi、Giulia Saponaro、Allan R. Moorman、Romeo Romagnoli、Delia Preti、Stefania Baraldi、Emanuela Ruggiero、Katia Varani、Martina Targa、Fabrizio Vincenzi、Pier Andrea Borea、Mojgan Aghazadeh Tabrizi

  DOI：10.1021/jm300763w

  日期：2012.7.26

  Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB(2) K-i = 2.5 nM, SI = 166; 21, hCB(2) K-i = 0.81 nM, SI = 383; 38, hCB(2) K-i = 15.8 nM, SI > 633; 56, hCB(2) K-i = 8.12 nM, SI > 1231; (R)-58, hCB(2) K-i = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.