N3-(1-adamantyl)-6-methyl-1-(2-(1,3-dioxolan-2-yl)ethyl)-4-oxo-1,4-dihydropyridine-3-carboxamide | 1403498-98-5

• 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: N3-(1-adamantyl)-6-methyl-1-(2-(1,3-dioxolan-2-yl)ethyl)-4-oxo-1,4-dihydropyridine-3-carboxamide
• 英文别名: N-(1-adamantyl)-1-[2-(1,3-dioxolan-2-yl)ethyl]-6-methyl-4-oxopyridine-3-carboxamide
• CAS: 1403498-98-5
• 化学式: C₂₂H₃₀N₂O₄
• 分子量: 386.491
• InChiKey: VFCBSIXZYGBWJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  金刚烷胺 、 6-methyl-4-oxo-1-(2-(1,3-dioxolan-2-yl)ethyl)-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54%的产率得到N3-(1-adamantyl)-6-methyl-1-(2-(1,3-dioxolan-2-yl)ethyl)-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

文献信息

• 4-Oxo-1,4-dihydropyridines as Selective CB₂ Cannabinoid Receptor Ligands Part 2: Discovery of New Agonists Endowed with Protective Effect Against Experimental Colitis
  作者：Jamal El Bakali、Pauline Gilleron、Mathilde Body-Malapel、Roxane Mansouri、Giulio G. Muccioli、Madjid Djouina、Amélie Barczyk、Frédérique Klupsch、Virginie Andrzejak、Emmanuelle Lipka、Christophe Furman、Didier M. Lambert、Philippe Chavatte、Pierre Desreumaux、Régis Millet

  DOI：10.1021/jm3008568

  日期：2012.10.25

  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.