N3-((1-adamantyl)methyl)-6-tert-butyl-4-oxo-1-pentyl-1,4-dihydropyridine-3-carboxamide | 1256650-76-6

• 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)methyl)-6-tert-butyl-4-oxo-1-pentyl-1,4-dihydropyridine-3-carboxamide
• 英文别名: N-(1-adamantylmethyl)-6-tert-butyl-4-oxo-1-pentylpyridine-3-carboxamide
• CAS: 1256650-76-6
• 化学式: C₂₆H₄₀N₂O₂
• 分子量: 412.616
• InChiKey: OWATUWQTDPKPDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基乙酰氯 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 N3-((1-adamantyl)methyl)-6-tert-butyl-4-oxo-1-pentyl-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

• 1,4-Dihydropyridine Derivatives and Their Uses
  申请人：Millet Regis

  公开号：US20120149735A1

  公开（公告）日：2012-06-14

  The present invention relates to 1,4-dihydropyridine derivatives of the formula (I) and their uses in the treatment and/or prevention of diseases and disorders directly or indirectly associated with the modification (increase or decrease) of the activity of the cannabinoid receptor 2 (CB2).

  本发明涉及式（I）的1,4-二氢吡啶衍生物及其在治疗和/或预防与大麻素受体2（CB2）的活性调节（增加或减少）直接或间接相关的疾病和障碍方面的用途。
• 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.