Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor

A series of substituted imidazoquinolines, a structurally related chemotype to pyrazoloquinolinones, a well-known class of GABA(A) ligands, was prepared via two synthetic procedures and the efficiency of these procedures were compared. One method relies on classical heterocyclic synthesis, the other...

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Autores principales: Draskovits, Markus, Catorci, Daniele, Wimmer, Laurin, Rehman, Sabah, Siebert, David Chan Bodin, Ernst, Margot, Schnürch, Michael, Mihovilovic, Marko D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2022
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10667396/
https://www.ncbi.nlm.nih.gov/pubmed/38020487
http://dx.doi.org/10.1007/s00706-022-02988-8
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author Draskovits, Markus
Catorci, Daniele
Wimmer, Laurin
Rehman, Sabah
Siebert, David Chan Bodin
Ernst, Margot
Schnürch, Michael
Mihovilovic, Marko D.
author_facet Draskovits, Markus
Catorci, Daniele
Wimmer, Laurin
Rehman, Sabah
Siebert, David Chan Bodin
Ernst, Margot
Schnürch, Michael
Mihovilovic, Marko D.
author_sort Draskovits, Markus
collection PubMed
description A series of substituted imidazoquinolines, a structurally related chemotype to pyrazoloquinolinones, a well-known class of GABA(A) ligands, was prepared via two synthetic procedures and the efficiency of these procedures were compared. One method relies on classical heterocyclic synthesis, the other one aims at late-stage decoration of a truncated scaffold via direct C–H functionalization. A pharmacological evaluation disclosed that one of the synthesized derivatives showed interesting activity on a α1β3 containing receptor subtype. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s00706-022-02988-8.
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spelling pubmed-106673962022-10-29 Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor Draskovits, Markus Catorci, Daniele Wimmer, Laurin Rehman, Sabah Siebert, David Chan Bodin Ernst, Margot Schnürch, Michael Mihovilovic, Marko D. Monatsh Chem Original Paper A series of substituted imidazoquinolines, a structurally related chemotype to pyrazoloquinolinones, a well-known class of GABA(A) ligands, was prepared via two synthetic procedures and the efficiency of these procedures were compared. One method relies on classical heterocyclic synthesis, the other one aims at late-stage decoration of a truncated scaffold via direct C–H functionalization. A pharmacological evaluation disclosed that one of the synthesized derivatives showed interesting activity on a α1β3 containing receptor subtype. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s00706-022-02988-8. Springer Vienna 2022-10-29 2023 /pmc/articles/PMC10667396/ /pubmed/38020487 http://dx.doi.org/10.1007/s00706-022-02988-8 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Original Paper
Draskovits, Markus
Catorci, Daniele
Wimmer, Laurin
Rehman, Sabah
Siebert, David Chan Bodin
Ernst, Margot
Schnürch, Michael
Mihovilovic, Marko D.
Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor
title Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor
title_full Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor
title_fullStr Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor
title_full_unstemmed Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor
title_short Novel synthetic procedures for C2 substituted imidazoquinolines as ligands for the α/β-interface of the GABAA-receptor
title_sort novel synthetic procedures for c2 substituted imidazoquinolines as ligands for the α/β-interface of the gabaa-receptor
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10667396/
https://www.ncbi.nlm.nih.gov/pubmed/38020487
http://dx.doi.org/10.1007/s00706-022-02988-8
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