1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester | 23789-91-5

• 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: 1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1,4-dihydro-4-oxo-1-(2-phenylethyl)-3-quinolinecarboxylate；N-(2-Phenylethyl)-4(1H)-chinolon-3-carbonsaeure-ethylester；Ethyl 4-oxo-1-(2-phenylethyl)quinoline-3-carboxylate
• CAS: 23789-91-5
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: QEYUUKOADCOMIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 吡啶 、 sodium hydroxide 、 tetraphosphorus decasulfide 、 草酸 作用下， 生成 2-Butyl-5-phenethyl-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,5-dihydropyrazolo[4,3-c]quinolin-3-ones, a novel series of PDE 4 inhibitors with low emetic potential and antiasthmatic properties

  摘要：

  A novel series of 2,5-dihydropyrazolo[4,3-c]quinolin-3-one has been prepared. These compounds showed good PDE 4 inhibitory activity and weak affinity for rolipram's binding site. They also exhibited a good anti-inflammatory profile without emetic side effects. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00548-5
• 作为产物：
  描述：

  (2-氟苯甲酰)乙酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  通过串联加成-消除-SNAr反应合成1,4-二氢-4-氧代-3-喹啉乙酯

  摘要：

  在几种药物化合物中很重要的1,4-二氢4-氧代-3-喹啉甲酸乙酯环结构是由2-（2-氟代苯甲酰基）乙酸乙酯分两步制备的。用N，N-二甲基甲酰胺二甲基乙缩醛处理这种β-酮酸酯可得到2-二甲基氨基亚甲基衍生物的97％收率。将此β-烯胺酮与伯胺在N，N-二甲基甲酰胺中在140°C下反应48小时，然后串联添加得到1,4-二氢-4-氧代-3-喹啉羧酸酯，收率60-74％。消除-S N Ar反应。介绍了起始材料的综合以及过程详细信息和机制方案。J.杂环化​​学。（2011）。

  DOI：

  10.1002/jhet.626

文献信息

• 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.
• Parallel synthesis of N-biaryl quinolone carboxylic acids as selective M1 positive allosteric modulators
  作者：Feng V. Yang、William D. Shipe、Jaime L. Bunda、M. Brad Nolt、David D. Wisnoski、Zhijian Zhao、James C. Barrow、William J. Ray、Lei Ma、Marion Wittmann、Matthew A. Seager、Kenneth A. Koeplinger、George D. Hartman、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2009.11.100

  日期：2010.1

  An iterative analog library synthesis approach was employed in the exploration of a quinolone carboxylic acid series of selective M-1 positive allosteric modulators, and strategies for improving potency and plasma free fraction were identified. (C) 2009 Elsevier Ltd. All rights reserved.
• Ethyl 1,4-dihydro-4-oxo-3-quinolinecarboxylates by a tandem addition-elimination-SNAr reaction
  作者：Richard A. Bunce、Eric J. Lee、Matthew T. Grant

  DOI：10.1002/jhet.626

  日期：2011.5

  The ethyl 1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylate ring structure, important in several drug compounds, has been prepared in two steps from ethyl 2‐(2‐fluorobenzoyl)acetate. Treatment of this β‐ketoester with N,N‐dimethylformamide dimethyl acetal gives a 97% yield of the 2‐dimethylaminomethylene derivative. Reaction of this β‐enaminone with primary amines in N,N‐dimethylformamide at 140°C for 48 h

  在几种药物化合物中很重要的1,4-二氢4-氧代-3-喹啉甲酸乙酯环结构是由2-（2-氟代苯甲酰基）乙酸乙酯分两步制备的。用N，N-二甲基甲酰胺二甲基乙缩醛处理这种β-酮酸酯可得到2-二甲基氨基亚甲基衍生物的97％收率。将此β-烯胺酮与伯胺在N，N-二甲基甲酰胺中在140°C下反应48小时，然后串联添加得到1,4-二氢-4-氧代-3-喹啉羧酸酯，收率60-74％。消除-S N Ar反应。介绍了起始材料的综合以及过程详细信息和机制方案。J.杂环化​​学。（2011）。
• Synthesis and biological evaluation of 2,5-dihydropyrazolo[4,3-c]quinolin-3-ones, a novel series of PDE 4 inhibitors with low emetic potential and antiasthmatic properties
  作者：Marı́a I Crespo、Jordi Gràcia、Carles Puig、Armando Vega、Josep Bou、Jordi Beleta、Teresa Doménech、Hamish Ryder、Vı́ctor Segarra、José M Palacios

  DOI：10.1016/s0960-894x(00)00548-5

  日期：2000.12

  A novel series of 2,5-dihydropyrazolo[4,3-c]quinolin-3-one has been prepared. These compounds showed good PDE 4 inhibitory activity and weak affinity for rolipram's binding site. They also exhibited a good anti-inflammatory profile without emetic side effects. (C) 2000 Published by Elsevier Science Ltd.