ethyl 5-(2,2'-bithiophen-5-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-(2,2'-bithiophen-5-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(5-thiophen-2-ylthiophen-2-yl)pyrazole-3-carboxylate；ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(5-thiophen-2-ylthiophen-2-yl)pyrazole-3-carboxylate
• 化学式: C₂₁H₁₆Cl₂N₂O₂S₂
• 分子量: 463.408
• InChiKey: HZPCYIZBAQMNEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(2,2'-bithiophen-5-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以99%的产率得到5-(2,2'-bithiophen-5-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Pyrazole-type cannabinoid ligands conjugated with fluoro-deoxy-carbohydrates as potential PET-imaging agents: Synthesis and CB1/CB2 receptor affinity evaluation

  摘要：

  A novel class of cannabinoid ligands was synthesized in good overall yields by means of oxime-bio-conjugation between hydroxylamine-functionalized Rimonabant-type pyrazoles and fluoro-deoxy-carbohydrates (D-2-fluoro-deoxy-glucose, FDG, and D-5-fluoro-5-deoxy-ribose, FDR). FDR proved to be superior to FDG for bio-conjugation, as it occurred in milder conditions and at faster rate (rt, 20 min vs. 100 degrees C, 30 min). All of the title compounds showed relatively modest affinity for the CBI receptor (high nanomolar range) and selectivities vs. the CB2. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.03.006
• 作为产物：
  描述：

  1-(5-溴-噻吩-2-基)-1-丙酮 在 四(三苯基膦)钯 、 sodium 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 38.0h， 生成 ethyl 5-(2,2'-bithiophen-5-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Pyrazole-type cannabinoid ligands conjugated with fluoro-deoxy-carbohydrates as potential PET-imaging agents: Synthesis and CB1/CB2 receptor affinity evaluation

  摘要：

  A novel class of cannabinoid ligands was synthesized in good overall yields by means of oxime-bio-conjugation between hydroxylamine-functionalized Rimonabant-type pyrazoles and fluoro-deoxy-carbohydrates (D-2-fluoro-deoxy-glucose, FDG, and D-5-fluoro-5-deoxy-ribose, FDR). FDR proved to be superior to FDG for bio-conjugation, as it occurred in milder conditions and at faster rate (rt, 20 min vs. 100 degrees C, 30 min). All of the title compounds showed relatively modest affinity for the CBI receptor (high nanomolar range) and selectivities vs. the CB2. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.03.006