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Affinity of 3-acyl substituted 4-quinolones at the benzodiazepine site of GABAA receptors.

  • Erik Lager
  • Jakob Nilsson
  • Elsebet Østergaard Nielsen
  • Mogens Nielsen
  • Tommy Liljefors
  • Olov Sterner
Publishing year: 2008
Language: English
Pages: 6936-6948
Publication/Series: Bioorganic & Medicinal Chemistry
Volume: 16
Issue: 14
Document type: Journal article
Publisher: Elsevier

Abstract english

The finding that alkyl 1,4-dihydro-4-oxoquinoline-3-carboxylate and N-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxamide derivatives may be high-affinity ligands at the benzodiazepine binding site of the GABAA receptor, prompted a study of 3-acyl-1,4-dihydro-4-oxoquinoline (3-acyl-4-quinolones). In general, the affinity of the 3-acyl derivatives was found to be comparable with the 3-carboxylate and the 3-carboxamide derivatives, and certain substituents (e.g., benzyl) in position 6 were again shown to be important. As it is believed that the benzodiazepine binding site is situated between an α- and a γ-subunit in the GABAA receptor, selected compounds were tested on the α1β2γ2s, α2β2γ2s and α3β2γ2s GABAA receptor subtypes. The 3-acyl-4-quinolones display various degrees of selectivity for α1- versus α2- and α3-containing receptors, and high-affinity ligands essentially selective for α1 over α3 were developed.


  • Organic Chemistry
  • 3-Acyl-1
  • 4-dihydro-4-oxoquinolines
  • Benzodiazepine binding site
  • GABAA receptor
  • GABAA receptor subtypes
  • Pharmacophore model


  • ISSN: 0968-0896
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se


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