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

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Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin. / Lipeeva, Alla V.; Zakharov, Danila O.; Burova, Liubov G. et al.

In: Molecules, Vol. 24, No. 11, 2126, 05.06.2019.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{d71df73c93694f908360c617eac03866,

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

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.",

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

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

year = "2019",

month = jun,

day = "5",

doi = "10.3390/molecules24112126",

language = "English",

volume = "24",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "11",

}

RIS

TY - JOUR

T1 - Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

AU - Lipeeva, Alla V.

AU - Zakharov, Danila O.

AU - Burova, Liubov G.

AU - Frolova, Tatyana S.

AU - Baev, Dmitry S.

AU - Shirokikh, Ilia V.

AU - Evstropov, Alexander N.

AU - Sinitsyna, Olga I.

AU - Tolsikova, Tatyana G.

AU - Shults, Elvira E.

PY - 2019/6/5

Y1 - 2019/6/5

N2 - 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.

AB - 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.

KW - Antibacterial activity

KW - Coumarin

KW - CuAAC reaction

KW - Furocoumarin

KW - Sonogashira coupling

KW - antibacterial activity

KW - coumarin

KW - ANTICOAGULANT

KW - COPPER

KW - furocoumarin

KW - MOLECULAR DOCKING

KW - IN-VIVO

KW - PLANT COUMARINS

KW - DERIVATIVES

KW - TRANSFORMATIONS

UR - http://www.scopus.com/inward/record.url?scp=85066760383&partnerID=8YFLogxK

U2 - 10.3390/molecules24112126

DO - 10.3390/molecules24112126

M3 - Article

C2 - 31195697

AN - SCOPUS:85066760383

VL - 24

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 11

M1 - 2126

ER -

ID: 20529697