Download PDF
Synthesis 2022; 54(03): 658-666
DOI: 10.1055/a-1649-5317
paper

An Attempt to Achieve Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1,4]Diazepinones Delivers Selective Dopamine D2 Receptor Ligands

Sergey Grintsevich
a   Saint Petersburg State University, Saint Petersburg 199034, Russian Federation
,
Alexander Sapegin
a   Saint Petersburg State University, Saint Petersburg 199034, Russian Federation
,
Beata Duszyńska
b   Department of Medicinal Chemistry, Maj Institute of Pharmacology, Polish Academy of Sciences, 31-343 Kraków, Poland
,
Andrzej J. Bojarski
b   Department of Medicinal Chemistry, Maj Institute of Pharmacology, Polish Academy of Sciences, 31-343 Kraków, Poland
,
Mikhail Krasavin  ∗
a   Saint Petersburg State University, Saint Petersburg 199034, Russian Federation
c   Immanuel Kant Baltic Federal University, Kaliningrad 236016, Russian Federation
› Author AffiliationsThis research was supported by the Russian Science Foundation (grant no. 19-75-30008).
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Attempts to extend the hydrated imidazoline ring expansion (HIRE) strategy to a series of diarene-fused [1,4]diazepinones (earlier applied successfully to bis-pyrido substrate nevirapine) did not result in ring expansion but, rather, led to 2-aminoethyl side chain expulsion. This seeming setback (setting the limitations to the HIRE methodology substrate scope) led to the discovery of selective dopamine D2 ligands with elements of structure–activity relationships.

Key words

[1,4]diazepinones - fused imidazolinium moiety - hydrated imidazoline ring expansion - 2-aminoethyl side chain expulsion - selective dopamine D2 ligands

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1649-5317.
  • Supporting Information


Publication History

Received: 04 August 2021

Accepted after revision: 20 September 2021

Accepted Manuscript online:
20 September 2021

Article published online:
27 October 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Zhao C, Ye Z, Ma Z.-x, Wildmaan SA, Blaszczyk SA, Hu L, Guizei IA, Tang W. Nat. Commun. 2019; 10: 4015
    CrossrefPubMed
    • 2a Yet L. Chem. Rev. 2000; 100: 2963
      CrossrefPubMed
    • 2b Molander GA. Acc. Chem. Res. 1998; 31: 603
      Crossref
    • 2c Illuminati G, Mandolini L. Acc. Chem. Res. 1981; 14: 95
      Crossref
    • 2d Galli C, Mandolini L. Eur. J. Org. Chem. 2000; 3117
      Crossref
    • 2e Sharma A, Appukkuttan P, Van der Eycken E. Chem. Commun. 2012; 48: 1623
      CrossrefPubMed
    • 3a Reutskaya E, Sapegin A, Peintner S, Erdélyi M, Krasavin M. J. Org. Chem. 2021; 86: 5778
      CrossrefPubMed
    • 3b Grintsevich S, Sapegin A, Reutskaya E, Peintner S, Erdélyi M, Krasavin M. Eur. J. Org. Chem. 2020; 5664
      Crossref
    • 3c Sapegin A, Osipyan A, Krasavin M. Org. Biomol. Chem. 2017; 15: 2906
      CrossrefPubMed
    • 3d Osipyan A, Sapegin A, Novikov A, Krasavin M. J. Org. Chem. 2018; 83: 9707
      CrossrefPubMed
    • 3e Grintsevich S, Sapegin A, Reutskaya E, Krasavin M. Tetrahedron Lett. 2019; 60: 20
      Crossref
  • 4 Lavit K, Reutskaya E, Grintsevich S, Sapegin A, Krasavin M. Tetrahedron Lett. 2020; 61: 152423
    Crossref
  • 5 Slifirski G, Krol M, Kleps J, Ulenberg S, Belka M, Baczek T, Siwek A, Stachowicz K, Szewczyk B, Nowak G, Bojarski A, Kozioł AE, Turło J, Herrold F. Eur. J. Med. Chem. 2019; 166: 144
    CrossrefPubMed
  • 6 Beaulieu JM, Gainetdinov RR. Pharmacol. Rev. 2011; 63: 182
    CrossrefPubMed