1-(4-bromobenzyl)-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-bromobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-(4-bromobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate；ethyl 1-[(4-bromophenyl)methyl]-4-oxoquinoline-3-carboxylate
• 化学式: C₁₉H₁₆BrNO₃
• 分子量: 386.245
• InChiKey: BOJDGGRILYHEGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N-[(1,2-trans)-2-hydroxycyclohexyl]-4-oxo-1-[4-(1H-pyrazol-5-yl)benzyl]-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  DIHYDROQUINOLINONE COMPOUNDS AS MODULATORS OF THE MUSCARININC M1 RECEPTOR

  摘要：

  公开号：

  EP2821401B1
• 作为产物：
  描述：

  1,4-二氢-4-氧代-3-喹啉羧酸乙酯 、 对溴溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以95%的产率得到1-(4-bromobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
  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

文献信息

• HETEROCYCLIC COMPOUND AND USE THEREFOR
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20150126487A1

  公开（公告）日：2015-05-07

  The present invention provides a compound having a cholinergic muscarinic M1 receptor positive allosteric modulator activity, and useful as a prophylactic or therapeutic drug for Alzheimer's disease, schizophrenia, pain, a sleep disorder and the like. The present invention relates to a compound represented by the formula (I): wherein R 1 is an optionally substituted amino group or an optionally substituted cyclic amino group, R 2 and R 3 are each independently a hydrogen atom or a substituent, X is —CH═ or —N═, and ring A is an optionally substituted 5- to 10-membered ring, or a salt thereof.

  本发明提供了一种具有胆碱能肌动蛋白M1受体正变构调节剂活性的化合物，可用作预防或治疗阿尔茨海默病、精神分裂症、疼痛、睡眠障碍等药物。本发明涉及一种由式(I)表示的化合物：其中R1是可选取代的氨基或可选取代的环状氨基，R2和R3各自独立地是氢原子或取代基，X是—CH═或—N═，环A是可选取代的5-至10-成员环，或其盐。
• Heterocyclic compound and use therefor
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US09403802B2

  公开（公告）日：2016-08-02

  The present invention provides a compound having a cholinergic muscarinic M1 receptor positive allosteric modulator activity, and useful as a prophylactic or therapeutic drug for Alzheimer's disease, schizophrenia, pain, a sleep disorder and the like. The present invention relates to a compound represented by the formula (I): wherein R1 is an optionally substituted amino group or an optionally substituted cyclic amino group, R2 and R3 are each independently a hydrogen atom or a substituent, X is —CH═ or —N═, and ring A is an optionally substituted 5- to 10-membered ring, or a salt thereof.

  本发明提供了一种具有胆碱能肌动蛋白M1受体正变构调节剂活性的化合物，可用作防治阿尔茨海默病、精神分裂症、疼痛、睡眠障碍等药物。本发明涉及一种由公式（I）表示的化合物：其中R1是一个可选择取代的氨基团或可选择取代的环状氨基团，R2和R3各自独立地是氢原子或取代基，X是-CH═或-N═，环A是一个可选择取代的5-至10成员环，或其盐。
• 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.
• US9403802B2
  申请人：——

  公开号：US9403802B2

  公开（公告）日：2016-08-02
• 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.