4-Hydroxy-7-methoxyquinoline-3-carboxylic acid, cyclohexylamide | 1000376-75-9

• 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
• 英文名称: 4-Hydroxy-7-methoxyquinoline-3-carboxylic acid, cyclohexylamide
• 英文别名: N-cyclohexyl-7-methoxy-4-oxo-1H-quinoline-3-carboxamide
• CAS: 1000376-75-9
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: SWQIGCUSMIKUJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-7-methoxyquinoline-3-carboxylic acid, cyclohexylamide 、 N-(2-氯乙基)吗啉盐酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-cyclohexyl-7-methoxy-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists

  摘要：

  A series of new 1,8-naphthyridine and quinoline derivatives were synthesized and evaluated for their cannabinoid receptor affinity. In particular, compounds 2, 5, 11, and 13 showed a high CB2 affinity and CB2 versus CB1 selectivity, in agreement with molecular modeling studies. Furthermore, compound 2 also exhibited in vivo antinociceptive effects. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.089
• 作为产物：
  描述：

  环己胺 、 7-甲氧基-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 反应 24.0h， 以52%的产率得到4-Hydroxy-7-methoxyquinoline-3-carboxylic acid, cyclohexylamide
  参考文献：
  名称：

  New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists

  摘要：

  A series of new 1,8-naphthyridine and quinoline derivatives were synthesized and evaluated for their cannabinoid receptor affinity. In particular, compounds 2, 5, 11, and 13 showed a high CB2 affinity and CB2 versus CB1 selectivity, in agreement with molecular modeling studies. Furthermore, compound 2 also exhibited in vivo antinociceptive effects. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.089

文献信息

• New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists
  作者：Clementina Manera、Maria Grazia Cascio、Veronica Benetti、Marco Allarà、Tiziano Tuccinardi、Adriano Martinelli、Giuseppe Saccomanni、Elisa Vivoli、Carla Ghelardini、Vincenzo Di Marzo、Pier Luigi Ferrarini

  DOI：10.1016/j.bmcl.2007.09.089

  日期：2007.12

  A series of new 1,8-naphthyridine and quinoline derivatives were synthesized and evaluated for their cannabinoid receptor affinity. In particular, compounds 2, 5, 11, and 13 showed a high CB2 affinity and CB2 versus CB1 selectivity, in agreement with molecular modeling studies. Furthermore, compound 2 also exhibited in vivo antinociceptive effects. (c) 2007 Elsevier Ltd. All rights reserved.