90181-93-4Relevant academic research and scientific papers
Synthesis of 3-substituted 4-hydroxyquinolin-2-ones via C-acylation reactions of active methylene compounds with functionalized 3,1-benzoxazin-4- ones
Mitsos, Christos,Zografos, Alexandros,Igglessi-Markopoulou, Olga
, p. 1543 - 1561 (2007/10/03)
A general protocol for the construction of 4-hydroxyquinolin-2-ones is described. Benzoxazinones react with the anion of active methylene compounds to produce the functionalized C-acylation compounds in very good yields. These key intermediates are cyclized to the desired quinolinones (25-40) under basic conditions. Spectral data and physical characteristics for all compounds are reported.
3-Acyl-4-hydroxyquinolin-2(1H)-ones. Systemically Active Anticonvulsants Acting by Antagonism at the Glycine Site of the N-Methyl-D-Aspartate Receptor Complex
Rowley, Michael,Leeson, Paul D.,Stevenson, Graeme I.,Moseley, Angela M.,Stansfield, Ian,et al.
, p. 3386 - 3396 (2007/10/02)
Most full antagonists at the glycine site of the NMDA receptor contain a carboxylic acid, which we believe to be detrimental to penetration of the blood-brain barrier.By consideration of a pharmacophore, novel antagonists at this site have been designed in which the anionic functionality is a vinylogous acid, in the form of a 4-hydroxyquinolin-2(1H)-one.In this series, a 3-substituent is necessary for binding, and correct manipulation of this group leads to compounds such as the 3-(3-hydroxyphenyl)propargyl ester 24 (L-701,273), with an IC50 for displacement of -L-689,560 binding of 0.17 μM and Kb against NMDA in the cortical slice of 1.39 μM.Compounds were tested for their ability to prevent audiogenic seizure in DBA/2 mice; the most potent compound in this series is the cyclopropyl ketone 42 (L-701,252), with an ED50 of 4.1 mg/kg ip.A model is proposed for binding to the glycine site, in which an important interaction is of a putative receptor cation with the ?-system of the 3-substituent.
Pharmaceutically active 4-hydroxy-3-benzoyl-2-quinolone derivatives
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, (2008/06/13)
4-Hydroxy-2-quinolone derivatives are useful for their anti-inflammatory, anti-allergenic, antitussive and expectorant activity. Pharmaceutical compositions containing said compounds and pharmaceutically acceptable salts thereof and methods of treating humans and animals are described herein.
