N-(adamantan-1-yl)-6-(furan-2-yl)-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxamide | 1239604-14-8

• 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
• 英文名称: N-(adamantan-1-yl)-6-(furan-2-yl)-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxamide
• 英文别名: N-(adamantan-1-yl)-6-(furan-2-yl)-1-pentylquinolin-4(1H)-one-3-carboxamide；N-(1-adamantyl)-6-(furan-2-yl)-4-oxo-1-pentylquinoline-3-carboxamide
• CAS: 1239604-14-8
• 化学式: C₂₉H₃₄N₂O₃
• 分子量: 458.601
• InChiKey: JAVXSEZBTVKAOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-碘戊烷 在 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.34h， 生成 N-(adamantan-1-yl)-6-(furan-2-yl)-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Regioselective functionalization of quinolin-4(1H)-ones via sequential palladium-catalyzed reactions

  摘要：

  A practical and general synthesis of 1,3,6-trisubstituted quinolin-4(1H)-ones starting from 1-alkyl-6-bromo-3-iodoquinolin-4(1H)-one is described, based on regioselective sequential palladium-catalyzed cross-coupling reactions, namely Suzuki-Miyaura, Sonogashira and aminocarbonylation reactions, under microwave irradiation. Good substrate generality, ease of execution and practicability make this method exploitable for the generation of libraries of chemically diverse 4-quinolones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.134

文献信息

• Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 3. Synthesis, Structure−Affinity Relationships, and Pharmacological Characterization of 6-Substituted 4-Quinolone-3-carboxamides as Highly Selective Cannabinoid-2 Receptor Ligands
  作者：Serena Pasquini、Alessia Ligresti、Claudia Mugnaini、Teresa Semeraro、Lavinia Cicione、Maria De Rosa、Francesca Guida、Livio Luongo、Maria De Chiaro、Maria Grazia Cascio、Daniele Bolognini、Pietro Marini、Roger Pertwee、Sabatino Maione、Vincenzo Di Marzo、Federico Corelli

  DOI：10.1021/jm100123x

  日期：2010.8.26

  A set of quinolone-3-carboxamides 2 bearing diverse substituents at position 1, 3, and 6 of the bicyclic nucleus was prepared. Except for six compounds exhibiting K(i) > 100 nM, all the quinolone-3-carboxamides 2 proved to be high affinity CB2 ligands, with K(i) values ranging from 73.2 to 0.7 nM and selectivity [SI = K(i)(CB1)/K(i)(CB2)] varying from > 14285 to 1.9, with only 2ah exhibiting a reverse selectivity (SI < 1). In the formalin test of peripheral acute and inflammatory pain in mice, 2ae showed analgesic activity that was antagonized by a selective CB2 antagonist. By contrast, 2e was inactive per se and antagonized the effect of a selective CB2 agonist. Finally, 2g and 2p exhibited CB2 inverse agonist-like behavior in this in vivo test. However, two different functional assays carried out in vitro on 2e and 2g indicated for both compounds an overall inverse agonist activity at CB2 receptors.
• Regioselective functionalization of quinolin-4(1H)-ones via sequential palladium-catalyzed reactions
  作者：Claudia Mugnaini、Chiara Falciani、Maria De Rosa、Antonella Brizzi、Serena Pasquini、Federico Corelli

  DOI：10.1016/j.tet.2011.05.134

  日期：2011.8

  A practical and general synthesis of 1,3,6-trisubstituted quinolin-4(1H)-ones starting from 1-alkyl-6-bromo-3-iodoquinolin-4(1H)-one is described, based on regioselective sequential palladium-catalyzed cross-coupling reactions, namely Suzuki-Miyaura, Sonogashira and aminocarbonylation reactions, under microwave irradiation. Good substrate generality, ease of execution and practicability make this method exploitable for the generation of libraries of chemically diverse 4-quinolones. (C) 2011 Elsevier Ltd. All rights reserved.