3-Butoxy-4-methoxy-2-nitrobenzaldehyde | 1192134-01-2

• 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-Butoxy-4-methoxy-2-nitrobenzaldehyde
• 英文别名: 3-butoxy-4-methoxy-2-nitrobenzaldehyde
• CAS: 1192134-01-2
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: CWOXDOPWLQLVIX-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-Butoxy-4-methoxy-2-nitrobenzaldehyde 在 哌啶 、 盐酸 、 氯化亚砜 、 水 、 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 35.25h， 生成 7-methoxy-8-butyloxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 2-(4-amino-phenyl)ethylamide
  参考文献：
  名称：

  Fluorinated cannabinoid CB2 receptor ligands: Synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives

  摘要：

  Cannabinoid receptor 2 (CB2) plays an important role in human physiology and the pathophysiology of different diseases, including neuroinflammation, neurodegeneration, and cancer. Several classes of CB2 receptor ligands, including 2-oxoquinoline derivatives, have been previously reported. We report the synthesis and results of in vitro receptor binding of a focused library of new fluorinated 2-oxoquinoline CB2 ligands. Twelve compounds, 13-16 18, 19, 21-24, 27, and 28 were synthesized in good yields in multiple steps. Human U87 glioma cells expressing either hCB1 (control) or hCB2 were generated via lentiviral transduction. In vitro competitive binding assay was performed using [H-3]CP-55,940 in U87hCB1 and U87hCB2 cells. Inhibition constant (K-i) values of compounds 13-16, 18, 19, 21-24, 27, and 28 for CB2 were >10,000,2.8, 5.0, 2.4, 22, 0.8, 1.4, >10,000, 486, 58, 620, and 2400 nM, respectively, and those for CB1 were >10,000 nM. Preliminary in vitro results suggest that six of these compounds may be useful for therapy of neuropathic pain, neuroinflammatory diseases and immune disorders. In addition, compound 19, with its subnanomolar K-i value, could be radiolabeled with F-18 and explored for PET imaging of CB2 expression. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.062
• 作为产物：
  描述：

  异香兰素 在 nitronium tetrafluoborate 、 caesium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 3-Butoxy-4-methoxy-2-nitrobenzaldehyde
  参考文献：
  名称：

  Fluorinated cannabinoid CB2 receptor ligands: Synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives

  摘要：

  Cannabinoid receptor 2 (CB2) plays an important role in human physiology and the pathophysiology of different diseases, including neuroinflammation, neurodegeneration, and cancer. Several classes of CB2 receptor ligands, including 2-oxoquinoline derivatives, have been previously reported. We report the synthesis and results of in vitro receptor binding of a focused library of new fluorinated 2-oxoquinoline CB2 ligands. Twelve compounds, 13-16 18, 19, 21-24, 27, and 28 were synthesized in good yields in multiple steps. Human U87 glioma cells expressing either hCB1 (control) or hCB2 were generated via lentiviral transduction. In vitro competitive binding assay was performed using [H-3]CP-55,940 in U87hCB1 and U87hCB2 cells. Inhibition constant (K-i) values of compounds 13-16, 18, 19, 21-24, 27, and 28 for CB2 were >10,000,2.8, 5.0, 2.4, 22, 0.8, 1.4, >10,000, 486, 58, 620, and 2400 nM, respectively, and those for CB1 were >10,000 nM. Preliminary in vitro results suggest that six of these compounds may be useful for therapy of neuropathic pain, neuroinflammatory diseases and immune disorders. In addition, compound 19, with its subnanomolar K-i value, could be radiolabeled with F-18 and explored for PET imaging of CB2 expression. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.062

文献信息

• Nucl. Med. Biol. 2009, 36, 455-465
  作者：

  DOI：——

  日期：——