Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin
| Autor: | Alexander N. Evstropov, Olga I. Sinitsyna, Ilia V. Shirokikh, Liubov G. Burova, Dmitry S. Baev, Danila O. Zakharov, A. V. Lipeeva, Elvira E. Shults, Tatyana G. Tolsikova, T. S. Frolova |
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| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
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2 3-Triazole Sonogashira coupling Pharmaceutical Science Microbial Sensitivity Tests medicine.disease_cause 01 natural sciences coumarin Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound furocoumarin antibacterial activity lcsh:Organic chemistry Furocoumarins Drug Discovery medicine Physical and Theoretical Chemistry CuAAC reaction Escherichia coli Bacteria 010405 organic chemistry Furocoumarin Organic Chemistry Triazoles Coumarin Combinatorial chemistry In vitro Anti-Bacterial Agents 0104 chemical sciences Molecular Docking Simulation 010404 medicinal & biomolecular chemistry chemistry Chemistry (miscellaneous) Docking (molecular) Staphylococcus aureus Drug Design Thermodynamics Molecular Medicine Antibacterial activity |
| Zdroj: | Molecules, Vol 24, Iss 11, p 2126 (2019) Molecules Volume 24 Issue 11 |
| ISSN: | 1420-3049 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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