6-methyl-4-oxo-1-prop-1-enyl-1,4-dihydropyridine-3-carboxylic acid | 1256650-89-1

• 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-prop-1-enyl-1,4-dihydropyridine-3-carboxylic acid
• 英文别名: 6-Methyl-4-oxo-1-prop-1-enylpyridine-3-carboxylic acid；6-methyl-4-oxo-1-prop-1-enylpyridine-3-carboxylic acid
• CAS: 1256650-89-1
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: SIJTYCGGUQHGJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl-4-oxo-1-prop-1-enyl-1,4-dihydropyridine-3-carboxylic acid 、 金刚烷胺 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15%的产率得到N3-(1-adamantyl)-6-methyl-1-prop-1-enyl-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 、 丙-1-烯-1-胺 在 potassium tert-butylate 、 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以54%的产率得到6-methyl-4-oxo-1-prop-1-enyl-1,4-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  [EN] 1,4 DIHYDROPYRIDINE DERIVATIVES AND THEIR USES
  [FR] DÉRIVÉS DE LA 1,4-DIHYDROPYRIDINE ET LEURS UTILISATIONS

  摘要：

  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）的活性修改（增加或减少）直接或间接相关的疾病和紊乱中的用途。

  公开号：

  WO2010133973A1

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.
• [EN] 1,4 DIHYDROPYRIDINE DERIVATIVES AND THEIR USES<br/>[FR] DÉRIVÉS DE LA 1,4-DIHYDROPYRIDINE ET LEURS UTILISATIONS
  申请人：UNIV LILLE II DROIT & SANTE

  公开号：WO2010133973A1

  公开（公告）日：2010-11-25

  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）的活性修改（增加或减少）直接或间接相关的疾病和紊乱中的用途。