PDF herunterladen
Synthesis 2024; 56(13): 2093-2099
DOI: 10.1055/s-0043-1763758
paper

Improved Synthesis and Preparation of Analogues of a Pain-Relieving Pyridin-2(1H)-one

Théo Frazier
a   Université Clermont Auvergne, CNRS, Clermont Auvergne INP, ICCF, 63000 Clermont-Ferrand, France
,
Pauline Murail
b   Université Clermont Auvergne, CHU Clermont-Ferrand, Inserm, Neuro-Dol, 63000 Clermont-Ferrand, France
,
Francis Giraud
a   Université Clermont Auvergne, CNRS, Clermont Auvergne INP, ICCF, 63000 Clermont-Ferrand, France
,
Alain Artola∗
b   Université Clermont Auvergne, CHU Clermont-Ferrand, Inserm, Neuro-Dol, 63000 Clermont-Ferrand, France
,
Radhouane Dallel∗
b   Université Clermont Auvergne, CHU Clermont-Ferrand, Inserm, Neuro-Dol, 63000 Clermont-Ferrand, France
,
Fabrice Anizon∗
a   Université Clermont Auvergne, CNRS, Clermont Auvergne INP, ICCF, 63000 Clermont-Ferrand, France
,
Pascale Moreau∗
a   Université Clermont Auvergne, CNRS, Clermont Auvergne INP, ICCF, 63000 Clermont-Ferrand, France
› InstitutsangabenThis research was financed by the French Government IDEX-ISITE Initiative 16-IDEX-0001 (CAP 20-25), Université Clermont-Auvergne, Institut National de la Santé et de la Recherche Médicale (Inserm), Centre National de la Recherche Scientifique (CNRS), and the Région Auvergne-Rhône-Alpes (Pack Ambition Recherche). The authors also thank WeylChem InnoTec (Frankfurt, Germany) for financial support.
› Weitere Informationen
    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

An optimization of the synthesis of 3,5-disubstituted pyridin-2(1H)-ones with in vivo anti-allodynic activity was conducted. The optimized synthesis was employed to prepare novel analogues which were then assessed for their efficacy in preventing cutaneous mechanical allodynia in a male rat hindpaw capsaicin model.

Key words

pyridin-2(1H)-ones - synthesis optimization - palladium catalysis - mechanical allodynia - analgesics

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1763758.
  • Supporting Information


Publikationsverlauf

Eingereicht: 17. April 2024

Angenommen nach Revision: 02. Mai 2024

Artikel online veröffentlicht:
22. Mai 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Treede R.-D, Rief W, Barke A, Aziz Q, Bennett MI, Benoliel R, Cohen M, Evers S, Finnerup NB, First MB, Giamberardino MA, Kaasa S, Korwisi B, Kosek E, Lavand’homme P, Nicholas M, Perrot S, Scholz J, Schug S, Smith BH, Svensson P, Vlaeyen JW. S, Wang S.-J. Pain 2019; 160: 19
    CrossrefPubMed
  • 2 Breivik H, Eisenberg E, O’Brien T. BMC Public Health 2013; 13: 1229
    CrossrefPubMed
  • 3 Fayaz A, Croft P, Langford RM, Donaldson LJ, Jones GT. BMJ Open 2016; 6: e010364
    CrossrefPubMed
  • 4 Dahlhamer J, Lucas J, Zelaya C, Nahin R, Mackey S, DeBar L, Kerns R, Von Korff M, Porter L, Helmick C. Morb. Mortal. Wkly. Rep. 2018; 67: 1001
    CrossrefPubMed
  • 5 Visseq A, Descheemaeker A, Pinto-Pardo N, Nauton L, Théry V, Giraud F, Abrunhosa-Thomas I, Artola A, Anizon F, Dallel R, Moreau P. Eur. J. Med. Chem. 2020; 187: 111917
    CrossrefPubMed
  • 6 Visseq A, Descheemaeker A, Hérault K, Giraud F, Abrunhosa-Thomas I, Artola A, Anizon F, Dallel R, Moreau P. Eur. J. Med. Chem. 2021; 225: 113748
    CrossrefPubMed
  • 7 Meyer-Eppler G, Küchler L, Tenten C, Benkhäuser C, Brück S, Lützen A. Synthesis 2014; 46: 1085
    Artikel in Thieme Connect
  • 8 Castro AC, McGovern KJ, Burke M. Pat. Appl. WO2021127301, 2021
    PubMed
  • 9 Singh BK, Cavalluzzo C, De Maeyer M, Debyser Z, Parmar VS, Van der Eycken E. Synthesis 2009; 2725
  • 10 Dallel R, Descheemaeker A, Luccarini P. Cephalalgia 2018; 38: 776
    CrossrefPubMed
  • 11 Peirs C, Bourgois N, Artola A, Dallel R. Anesthesiology 2016; 124: 1136
    CrossrefPubMed