3-amino-7-methoxy-8-pentyloxy-1H-quinolin-2-one | 883229-04-7

• 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: 3-amino-7-methoxy-8-pentyloxy-1H-quinolin-2-one
• 英文别名: 3-Amino-8-amoxy-7-methoxy-carbostyril；3-amino-7-methoxy-8-pentoxy-1H-quinolin-2-one
• CAS: 883229-04-7
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: DCBHOYLBETVIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-7-methoxy-8-pentyloxy-1H-quinolin-2-one 、 苯并[1,3]二氧代-5-乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以30 mg的产率得到2-(1,3-benzodioxol-5-yl)-N-(7-methoxy-2-oxo-8-pentoxy-1H-quinolin-3-yl)acetamide
  参考文献：
  名称：

  Synthesis and SAR Studies of 2-Oxoquinoline Derivatives as CB2 Receptor Inverse Agonists

  摘要：

  The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and effective CB2 receptor inverse agonists. A series of aromatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 was synthesized, and the CB2 receptor activities of the compounds were determined by a [S-35]GTP(gamma)S-binding assay using membranes of CHO cells stably transfected with the human CB2 receptor. As a result, all the compounds were defined as full CB2 receptor inverse agonists, and additionally, except for two 3,4-dihydroxyphenylalkylamides, they were found to be equally potent as SR144528.

  DOI：

  10.1021/jm050879z
• 作为产物：
  描述：

  7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 在 ammonium hydroxide 、 氯化亚砜 、 sodium hypobromide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 7.75h， 生成 3-amino-7-methoxy-8-pentyloxy-1H-quinolin-2-one
  参考文献：
  名称：

  Synthesis and SAR Studies of 2-Oxoquinoline Derivatives as CB2 Receptor Inverse Agonists

  摘要：

  The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and effective CB2 receptor inverse agonists. A series of aromatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 was synthesized, and the CB2 receptor activities of the compounds were determined by a [S-35]GTP(gamma)S-binding assay using membranes of CHO cells stably transfected with the human CB2 receptor. As a result, all the compounds were defined as full CB2 receptor inverse agonists, and additionally, except for two 3,4-dihydroxyphenylalkylamides, they were found to be equally potent as SR144528.

  DOI：

  10.1021/jm050879z

文献信息

• Synthesis and SAR Studies of 2-Oxoquinoline Derivatives as CB2 Receptor Inverse Agonists
  作者：Katri H. Raitio、Juha R. Savinainen、Jouko Vepsäläinen、Jarmo T. Laitinen、Antti Poso、Tomi Järvinen、Tapio Nevalainen

  DOI：10.1021/jm050879z

  日期：2006.3.1

  The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and effective CB2 receptor inverse agonists. A series of aromatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 was synthesized, and the CB2 receptor activities of the compounds were determined by a [S-35]GTP(gamma)S-binding assay using membranes of CHO cells stably transfected with the human CB2 receptor. As a result, all the compounds were defined as full CB2 receptor inverse agonists, and additionally, except for two 3,4-dihydroxyphenylalkylamides, they were found to be equally potent as SR144528.