1-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

• 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: 1-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate；Ethyl 1-[(4-fluorophenyl)methyl]-4-oxoquinoline-3-carboxylate
• 化学式: C₁₉H₁₆FNO₃
• 分子量: 325.339
• InChiKey: ALEACMUPCYWHBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到1-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality

  摘要：

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

  DOI：

  10.1021/jm070387h
• 作为产物：
  描述：

  1,4-二氢-4-氧代-3-喹啉羧酸乙酯 、 4-氟溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Quinolinonyl Non-Diketo Acid Derivatives as Inhibitors of HIV-1 Ribonuclease H and Polymerase Functions of Reverse Transcriptase

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00535

文献信息

• Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat–TAR interaction inhibitors
  作者：Shuguang Chen、Ran Chen、Meizi He、Ruifang Pang、Zhiwu Tan、Ming Yang

  DOI：10.1016/j.bmc.2009.01.038

  日期：2009.3

  Thirty-two quinoline derivatives were designed and synthesized as HIV-1 Tat–TAR interaction inhibitors. All the compounds showed high antiviral activities in inhibiting the formation of SIV-induced syncytium in CEM174 cells. Nine of them with low cytotoxicities were evaluated by Tat dependent HIV-1 LTR-driven CAT gene expression colorimetric enzyme assay in human 293T cells, indicating effective inhibitory

  设计并合成了32种喹啉衍生物作为HIV-1 Tat-TAR相互作用抑制剂。所有这些化合物在抑制CEM174细胞中SIV诱导的合胞体形成方面均表现出很高的抗病毒活性。在人的293T细胞中，通过Tat依赖HIV-1 LTR驱动的CAT基因表达比色酶分析评估了其中9种低细胞毒性，表明它们具有有效的抑制Tat-TAR相互作用的抑制活性。分子模拟实验表明，这些化合物可能通过与Tat蛋白而非TAR RNA结合而抑制Tat-TAR相互作用。
• Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality
  作者：Eric Stern、Giulio G. Muccioli、Barbara Bosier、Laurie Hamtiaux、Régis Millet、Jacques H. Poupaert、Jean-Pierre Hénichart、Patrick Depreux、Jean-François Goossens、Didier M. Lambert

  DOI：10.1021/jm070387h

  日期：2007.11.1

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.
• Quinolinonyl Non-Diketo Acid Derivatives as Inhibitors of HIV-1 Ribonuclease H and Polymerase Functions of Reverse Transcriptase
  作者：Antonella Messore、Angela Corona、Valentina Noemi Madia、Francesco Saccoliti、Valeria Tudino、Alessandro De Leo、Davide Ialongo、Luigi Scipione、Daniela De Vita、Giorgio Amendola、Ettore Novellino、Sandro Cosconati、Mathieu Métifiot、Marie-Line Andreola、Francesca Esposito、Nicole Grandi、Enzo Tramontano、Roberta Costi、Roberto Di Santo

  DOI：10.1021/acs.jmedchem.1c00535

  日期：2021.6.24