7-methoxy-2-oxo-8-(pentyloxy)-1,2-dihydroquinoline-3-carboxamide | 283592-58-5

• 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: 7-methoxy-2-oxo-8-(pentyloxy)-1,2-dihydroquinoline-3-carboxamide
• 英文别名: 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxamide；7-methoxy-2-oxo-8-pentoxy-1H-quinoline-3-carboxamide
• CAS: 283592-58-5
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: YWSRDNYZSGPAOD-UHFFFAOYSA-N

物化性质

• 沸点：
  568.5±50.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-oxo-8-(pentyloxy)-1,2-dihydroquinoline-3-carboxamide 在 sodium hypobromide 作用下， 反应 1.25h， 以39%的产率得到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
• 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 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 6.5h， 生成 7-methoxy-2-oxo-8-(pentyloxy)-1,2-dihydroquinoline-3-carboxamide
  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

• Step-economical synthesis of 3-amido-2-quinolones by dendritic copper powder-mediated one-pot reaction
  作者：Byung Hoon Ahn、Ill Young Lee、Hee Nam Lim

  DOI：10.1039/c8ob01994k

  日期：——

  The one-pot protocol by the dendritic copper powder-mediated Knoevenagel condensation/annelation is delineated here for the synthesis of 3-amido-2-quinolones. It is practical with moisture tolerance and easy setup, and is compatible with many functional groups under mild conditions. This method was applied for the preparation of the key intermediates of biologically relevant 3-amido-2-quinolones.

  这里描述了通过树枝状铜粉介导的Knoevenagel缩合/退火的一锅法方案，用于合成3-酰胺基-2-喹诺酮。它具有耐湿性和易于设置的实用性，并且在温和条件下与许多官能团兼容。该方法用于制备生物学上相关的3-酰胺基-2-喹诺酮的关键中间体。
• Antipruritics
  申请人：Yasui Kiyoshi

  公开号：US20050101590A1

  公开（公告）日：2005-05-12

  It is intended to provide antipruritics (drugs to control itching, antiitch agents and drugs to stop itching). It is found out that a compound having an agonistic activity to the cannabinoid receptor shows an antipruritics effect.

  这意味着它旨在提供止痒药（用于控制瘙痒的药物，抗瘙痒剂和止痒药）。研究发现，具有激动性作用的大麻素受体的化合物具有止痒效果。
• 2-oxoquinoline compounds and pharmaceutical uses thereof
  申请人：——

  公开号：US20030191069A1

  公开（公告）日：2003-10-09

  A 2-oxoquinoline compound or its pharmaceutically acceptable salt of general formula [I]: 1 (wherein each symbol in the formula is as determined in the description), and its pharmaceutical use. The compound [I] of the present invention and its pharmaceutically acceptable salts selectively act on cannabinoid receptors, particularly on peripheral type cannabinoid receptors, and have fewer side effects on the central nervous system, having great immunosuppressive action, anti-inflammatory action or antiallergic action. Therefore, these compounds are useful as cannabinoid receptors (particularly peripheral type cannabinoid receptors) modulator, immunosuppressants, anti-inflammatory agents, and antiallergic agents.

  一种2-氧基喹啉化合物或其药学上可接受的盐，其通式为[I]:1（其中公式中的每个符号如说明中所确定的那样），以及其医药用途。本发明的化合物[I]及其药学上可接受的盐，能够选择性地作用于大麻素受体，特别是外周型大麻素受体，并且对中枢神经系统的副作用较少，具有很强的免疫抑制作用、抗炎作用或抗过敏作用。因此，这些化合物可用作大麻素受体（特别是外周型大麻素受体）调节剂、免疫抑制剂、抗炎剂和抗过敏剂。
• 2-OXOQUINOLINE COMPOUNDS AND MEDICINAL USES THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP1142877A1

  公开（公告）日：2001-10-10

  A 2-oxoquinoline compound or its pharmaceutically acceptable salt of general formula [I]: (wherein each symbol in the formula is as determined in the description), and its pharmaceutical use. The compound [I] of the present invention and its pharmaceutically acceptable salts selectively act on cannabinoid receptors, particularly on peripheral type cannabinoid receptors, and have fewer side effects on the central nervous system, having great immunosuppressive action, anti-inflammatory action or antiallergic action. Therefore, these compounds are useful as cannabinoid receptors (particularly peripheral type cannabinoid receptors) modulator, immunosuppressants, anti-inflammatory agents, and antiallergic agents.

  通式[I]的 2-氧代喹啉化合物或其药学上可接受的盐： (其中式中各符号由说明中确定）及其药物用途。 本发明的化合物[I]及其药学上可接受的盐选择性地作用于大麻素受体，特别是外周型大麻素受体，对中枢神经系统的副作用较小，具有很好的免疫抑制作用、抗炎作用或抗过敏作用。因此，这些化合物可用作大麻素受体（特别是外周型大麻素受体）调节剂、免疫抑制剂、抗炎剂和抗过敏剂。
• ANTIPRURITICS
  申请人：SHIONOGI & CO., LTD.

  公开号：EP1477186A1

  公开（公告）日：2004-11-17

  It is intended to provide antipruritics (drugs to control itching, antiitch agents and drugs to stop itching). It is found out that a compound having an agonistic activity to the cannabinoid receptor shows an antipruritics effect.

  其目的是提供止痒药（控制瘙痒的药物、止痒剂和止痒药）。研究发现，一种对大麻素受体具有激动活性的化合物具有止痒效果。