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

Molecules

AlexanderN. Evstropov¹  LiubovG. Burova¹  IliaV. Shirokikh¹  DmitryS. Baev²  TatyanaG. Tolsikova²  ElviraE. Shults²  AllaV. Lipeeva²  DanilaO. Zakharov²  TatyanaS. Frolova³  OlgaI. Sinitsyna³ 

[1] Department of Microbiology, Immunology and Virology, Novosibirsk State Medical University, Krasny Prospect 52, 630091 Novosibirsk, Russia;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentyev Ave. 9, 630090 Novosibirsk, Russia;The Federal Research Center Institute of Cytology and Genetics, Acad. Lavrentyev Ave. 10, 630090 Novosibirsk, Russia;

关键词: coumarin;    furocoumarin;    Sonogashira coupling;    CuAAC reaction;    antibacterial activity;   

DOI  :  10.3390/molecules24112126

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown