Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

Alla V. Lipeeva, Danila O. Zakharov, Liubov G. Burova, Tatyana S. Frolova, Dmitry S. Baev, Ilia V. Shirokikh, Alexander N. Evstropov, Olga I. Sinitsyna, Tatyana G. Tolsikova, Elvira E. Shults

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Synthesis of 1,2,3-triazole-substituted coumarins and also 1,2,3-triazolyl or 1,2,3-triazolylalk-1-inyl-linked coumarin-2,3-furocoumarin hybrids was performed by employing the cross-coupling and copper catalyzed azide-alkyne cycloaddition reaction approaches. The synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Bacillius subtilis, Actinomyces viscosus and Escherichia coli bacterial strains. Coumarin-benzoic acid hybrids 4с, 42с and 3-((4-acetylamino-3-(methoxycarbonyl)phenyl)ethynyl)coumarin (29) showed promising activity against S. aureus strains, and the 1,2,3-triazolyloct-1-inyl linked coumarin-2,3-furocoumarin hybrid 37c was endowed with high selectivity against B. subtilis and E. coli species. The in vitro antibacterial activity of 4с, 29, 37c and 42с can potentially be compared with that of a number of modern antibiotic drugs used in the clinic, suggesting promising prospects for further research. A detailed study of the molecular interactions with the targeted protein MurB was performed using docking simulations and the obtained results are quite promising.

Original languageEnglish
Article number2126
Number of pages23
JournalMolecules
Volume24
Issue number11
DOIs
Publication statusPublished - 5 Jun 2019

Keywords

  • Antibacterial activity
  • Coumarin
  • CuAAC reaction
  • Furocoumarin
  • Sonogashira coupling
  • antibacterial activity
  • coumarin
  • ANTICOAGULANT
  • COPPER
  • furocoumarin
  • MOLECULAR DOCKING
  • IN-VIVO
  • PLANT COUMARINS
  • DERIVATIVES
  • TRANSFORMATIONS

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