N-(金刚烷-1-基)-6-异丙基-4-氧代-1-戊基-1,4-二氢喹啉-3-甲酰胺 | 1048038-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: N-(金刚烷-1-基)-6-异丙基-4-氧代-1-戊基-1,4-二氢喹啉-3-甲酰胺
• 英文名称: N-(adamant-1-yl)-6-isopropyl-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxamide
• 英文别名: N-(adamantan-1-yl)-6-isopropyl-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxamide；1,4-dihydro-6-(1-methylethyl)-4-oxo-1-pentyl-N-tricyclo[3.3.1.1^3,7]dec-1-yl-3-quinolinecarboxamide；N-(1-adamantyl)-4-oxo-1-pentyl-6-propan-2-ylquinoline-3-carboxamide
• CAS: 1048038-90-9
• 化学式: C₂₈H₃₈N₂O₂
• 分子量: 434.622
• InChiKey: KUMKLUDNETVLDS-UHFFFAOYSA-N

物化性质

• 密度：
  1.15
• 溶解度：
  DMF:5.0(最大浓度 mg/mL);11.5(最大浓度 mM)乙醇:3.0(最大浓度 mg/mL);6.9(最大浓度 mM)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  N-(adamantan-1-yl)-6-(propan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 N-(金刚烷-1-基)-6-异丙基-4-氧代-1-戊基-1,4-二氢喹啉-3-甲酰胺
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 2. Synthesis and Structure−Activity Relationship of Potent and Selective Cannabinoid-2 Receptor Agonists Endowed with Analgesic Activity in Vivo

  摘要：

  Quinolone-3-carboxamides 11 bearing at position 5, 6, 7, or 8 diverse substituents such as halides, alkyl, aryl, alkoxy, and aryloxy groups differing in their steric/electronic properties, were prepared. The new compounds were tested in vitro for CB1 and CB2 receptor affinity in comparison with the reference compounds rimonabant and SR144528. The tested compounds exhibited CB2 affinity in the ran, e from 55.9 to 0.8 nM and CB1 affinity in the range from > 10 000 to 5.3 nM, with selectivity indeces [K-i(CB1)/K-i(CB2)] varying from > 2666.6 to 1.23. On the basis of the structure-selectivity relationship developed, the presence of a substituent at C6/C8 or C7 well accounts for the high or low CB2 selectivity, respectively. Compound 11c, characterized by high CB2 affinity and selectivity, showed analgesic activity in the formalin test of acute peripheral and inflammatory pain in mice as a result of selective CB2 agonistic activity.

  DOI：

  10.1021/jm800552f

文献信息

• Use of heme oxygenase 1 inducers and cannabinoid 2 receptor or delta-opioid receptor agonists in inflammatory pain
  申请人：Fundació Institut de Recerca de l'Hospital de la Santa Creu l Sant Pau

  公开号：EP2992880A1

  公开（公告）日：2016-03-09

  The present invention relates to a combination comprising at least an heme oxygenase 1 inducer, and at least a cannabinoid 2 receptor agonist or a selective δ-opioid receptor agonist, for use in the prevention and/or treatment of inflammatory pain.

  本发明涉及一种组合物，至少包含一种血红素加氧酶 1 诱导剂和至少一种大麻素 2 受体激动剂或一种选择性 δ-阿片受体激动剂，用于预防和/或治疗炎症性疼痛。