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

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

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2019, Volume: 24, Number: 11, Article number : 2126, Pages count : DOI: 10.3390/molecules24112126

Tags

coumarin; furocoumarin; Sonogashira coupling; CuAAC reaction; antibacterial activity

Authors

Lipeeva Alla V. ¹ , Zakharov Danila O. ¹ , Burova Liubov G. ² , Frolova Tatyana S. ^3,4 , Baev Dmitry S. ¹ , Shirokikh Ilia V. ² , Evstropov Alexander N. ² , Sinitsyna Olga I. ^3,4 , Tolsikova Tatyana G. ¹ , Shults Elvira E. ^1,4

Affiliations

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Organ Chem Inst, Siberian Branch, Lavrentyev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Med Univ, Dept Microbiol Immunol & Virol, Krasny Prospect 52, Novosibirsk 630091, Russia
3	(Данные Web of science) Fed Res Ctr Inst Cytol & Genet, Acad Lavrentyev Ave 10, Novosibirsk 630090, Russia
4	(Данные Web of science) Novosibirsk State Univ, Pirogova Str 1, Novosibirsk 630090, Russia

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 4?, 42? 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 4?, 29, 37c and 42? 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.

Lipeeva A.V. , Zakharov D.O. , Burova L.G. , Frolova T.S. , Baev D.S. , Shirokikh I.V. , Evstropov A.N. , Sinitsyna O.I. , Tolsikova T.G. , Shults E.E.
Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

Molecules. 2019. V.24. N11. 2126 . DOI: 10.3390/molecules24112126 WOS Scopus РИНЦ

Full text from publisher

Published online:

Jun 5, 2019

Web of science	WOS:000472631000099
Scopus	2-s2.0-85066760383
Elibrary	41625696
OpenAlex	W2948623028