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

• Published in: Molecules (Basel, Switzerland) Vol. 24; no. 11; p. 2126
• Main Authors: Lipeeva, Alla V, Zakharov, Danila O, Burova, Liubov G, Frolova, Tatyana S, Baev, Dmitry S, Shirokikh, Ilia V, Evstropov, Alexander N, Sinitsyna, Olga I, Tolsikova, Tatyana G, Shults, Elvira E
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 05.06.2019; MDPI
• Subjects: Alkynes; Amino acids; Antibacterial activity; Antibiotics; Antimicrobial agents; Benzoic acid; Chromatography; Coumarin; Cross coupling; CuAAC reaction; Cycloaddition; Drug resistance; furocoumarin; Hybrids; Hydrocarbons; Molecular interactions; Pathogens; Selectivity; Sonogashira coupling; Staphylococcus aureus; Strains (organisms); Triazoles; Sonogashira coupling; antibacterial activity; CuAAC reaction; furocoumarin; coumarin
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24112126

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 , , and bacterial strains. Coumarin-benzoic acid hybrids , and 3-((4-acetylamino-3-(methoxycarbonyl)phenyl)ethynyl)coumarin ( ) showed promising activity against . strains, and the 1,2,3-triazolyloct-1-inyl linked coumarin-2,3-furocoumarin hybrid was endowed with high selectivity against and species. The in vitro antibacterial activity of , , and 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.