6-(2,4-二氯苄基)-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 | 1048998-68-0

• 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: 6-(2,4-二氯苄基)-4-氧代-1,4-二氢喹啉-3-羧酸乙酯
• 英文名称: ethyl 6-(2,4-dichlorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS: 1048998-68-0
• 化学式: C₁₉H₁₅Cl₂NO₃
• 分子量: 376.239
• InChiKey: MQAIZIPBPOBMNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  59.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(2,4-二氯苄基)-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 、 2-氯-N,N-二甲基乙胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到ethyl 6-(2,4-dichlorobenzyl)-1-(2-(dimethylamino)ethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 1. Synthesis and Structure−Activity Relationship of a Class of Human Immunodeficiency Virus type 1 Integrase Inhibitors

  摘要：

  A set of 4-quinolone-3-carboxylic acids bearing different substituents on the condensed benzene ring was designed and synthesized as potential HIV-1 integrase inhibitors structurally related to elvitegravir. Some of the new compounds proved to be able to inhibit the strand transfer step of the virus integration process in the micromolar range. Docking studies and quantum mechanics calculations were used to rationalize these data.

  DOI：

  10.1021/jm8003784
• 作为产物：
  描述：

  以 二苯醚 为溶剂， 反应 2.0h， 生成 6-(2,4-二氯苄基)-4-氧代-1,4-二氢喹啉-3-羧酸乙酯
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 1. Synthesis and Structure−Activity Relationship of a Class of Human Immunodeficiency Virus type 1 Integrase Inhibitors

  摘要：

  A set of 4-quinolone-3-carboxylic acids bearing different substituents on the condensed benzene ring was designed and synthesized as potential HIV-1 integrase inhibitors structurally related to elvitegravir. Some of the new compounds proved to be able to inhibit the strand transfer step of the virus integration process in the micromolar range. Docking studies and quantum mechanics calculations were used to rationalize these data.

  DOI：

  10.1021/jm8003784

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.