PDF herunterladen
Synthesis
DOI: 10.1055/a-2746-2444
Paper

Synthesis and In Silico Study of Multifunctional Arylthio-Tetrafluorobenzene-Imidazole Triad Compounds

Autoren

  • Nailya F. Vaskina

    1   Department of Organic & Biomolecular Chemistry, Ural Federal University, Ekaterinburg, Russia (Ringgold ID: RIN64974)

  • Egor A. Nikiforov 

    1   Department of Organic & Biomolecular Chemistry, Ural Federal University, Ekaterinburg, Russia (Ringgold ID: RIN64974)

  • Timofey D. Moseev 

    1   Department of Organic & Biomolecular Chemistry, Ural Federal University, Ekaterinburg, Russia (Ringgold ID: RIN64974)

  • Mikhail V. Varaksin 

    1   Department of Organic & Biomolecular Chemistry, Ural Federal University, Ekaterinburg, Russia (Ringgold ID: RIN64974)
    2   Ural Branch of the Russian Academy of Sciences, I.Ya. Postovsky Institute of Organic Synthesis, Ekaterinburg, Russia

  • Ilya I. Butorin

    1   Department of Organic & Biomolecular Chemistry, Ural Federal University, Ekaterinburg, Russia (Ringgold ID: RIN64974)

  • Valery Charushin

    1   Department of Organic & Biomolecular Chemistry, Ural Federal University, Ekaterinburg, Russia (Ringgold ID: RIN64974)
    2   Ural Branch of the Russian Academy of Sciences, I.Ya. Postovsky Institute of Organic Synthesis, Ekaterinburg, Russia

  • Oleg N. Chupakhin 

    1   Department of Organic & Biomolecular Chemistry, Ural Federal University, Ekaterinburg, Russia (Ringgold ID: RIN64974)
    2   Ural Branch of the Russian Academy of Sciences, I.Ya. Postovsky Institute of Organic Synthesis, Ekaterinburg, Russia

This research was financially supported by the Russian Science Foundation, project no. 23-63-10011, https://www.rscf.ru/en/project/23-63-10011/.
Weitere Informationen
   Lizenzen und Reprints Alle Artikel dieser Rubrik


Graphical Abstract

Abstract

An original, transition metal-free, two-step synthetic strategy based on sequential SN H and SN Ar reactions, namely C–H functionalization of nonaromatic 2H-imidazole 1-oxide with pentafluorophenyl lithium followed by aromatic fluorine substitution with arylthioles, was proposed. A series of new arylthio-tetrafluorobenzene-imidazole triad multifunctional compounds were prepared in good yields of 62–94%. The in silico study of the synthesized triads toward biotargets associated with endothelial dysfunction (PDE5a); cancer (EGFR, CDK2); and SARS-CoV-2 viral infection (Mpro) revealed that biotarget binding selectivity was highly sensitive to the positioning of substituents on the aromatic ring. The synthesized triads could be considered as perspective lead compounds in the design of agents for pharmaceutical applications.

Keywords

Imidazole - Arylthiol - Fluoroarene - Multifunctional compounds - Nucleophilic substitution

Supplementary Material



Publikationsverlauf

Eingereicht: 04. September 2025

Angenommen nach Revision: 12. November 2025

Artikel online veröffentlicht:
09. Dezember 2025

© 2025. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany