6-methyl-4-oxo-1-(4,4,4-trifluorobutyl)-1,4-dihydropyridine-3-carboxylic acid | 1403498-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-methyl-4-oxo-1-(4,4,4-trifluorobutyl)-1,4-dihydropyridine-3-carboxylic acid
• 英文别名: 6-Methyl-4-oxo-1-(4,4,4-trifluorobutyl)pyridine-3-carboxylic acid；6-methyl-4-oxo-1-(4,4,4-trifluorobutyl)pyridine-3-carboxylic acid
• CAS: 1403498-95-2
• 化学式: C₁₁H₁₂F₃NO₃
• 分子量: 263.216
• InChiKey: GYYPGZBDVNBOJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  金刚烷胺 、 6-methyl-4-oxo-1-(4,4,4-trifluorobutyl)-1,4-dihydropyridine-3-carboxylic acid 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以39%的产率得到N-adamantyl-1-(4,4,4-trifluorobutyl)-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  4-Oxo-1,4-dihydropyridines as Selective CB₂ Cannabinoid Receptor Ligands Part 2: Discovery of New Agonists Endowed with Protective Effect Against Experimental Colitis

  摘要：

  Further on to our earlier work on the 4-oxo-1,4-dihydropyridine, we describe herein our strategy to get access to potent selective CB2 receptor agonists. Thus, we designed and synthesized 29 compounds, evaluated on both hCB(1) and hCB(2) cannabinoid receptors, and assessed 11 of them in the TNBS-induced colitis model in mice. Compound 48 was found to be the most efficient of our series, exhibiting an exquisite protection against experimental colitis, superior to the one observed after treatment with Pentasa.

  DOI：

  10.1021/jm3008568
• 作为产物：
  描述：

  3-(dimethylaminomethylene)-6-methylpyran-2,4-dione 、 4,4,4-三氟丁胺 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以71%的产率得到6-methyl-4-oxo-1-(4,4,4-trifluorobutyl)-1,4-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  4-Oxo-1,4-dihydropyridines as Selective CB₂ Cannabinoid Receptor Ligands Part 2: Discovery of New Agonists Endowed with Protective Effect Against Experimental Colitis

  摘要：

  Further on to our earlier work on the 4-oxo-1,4-dihydropyridine, we describe herein our strategy to get access to potent selective CB2 receptor agonists. Thus, we designed and synthesized 29 compounds, evaluated on both hCB(1) and hCB(2) cannabinoid receptors, and assessed 11 of them in the TNBS-induced colitis model in mice. Compound 48 was found to be the most efficient of our series, exhibiting an exquisite protection against experimental colitis, superior to the one observed after treatment with Pentasa.

  DOI：

  10.1021/jm3008568