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Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers. / Patrushev, S. S.; Vasil’eva, D. O.; Burova, L. G. et al.

In: Russian Chemical Bulletin, Vol. 72, No. 10, 10.2023, p. 2513-2524.

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

Harvard

Patrushev, SS, Vasil’eva, DO, Burova, LG, Bondareva, EA, Zakharova, LN, Evstropov, AN & Shults, EE 2023, 'Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers', Russian Chemical Bulletin, vol. 72, no. 10, pp. 2513-2524. https://doi.org/10.1007/s11172-023-4054-0

APA

Patrushev, S. S., Vasil’eva, D. O., Burova, L. G., Bondareva, E. A., Zakharova, L. N., Evstropov, A. N., & Shults, E. E. (2023). Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers. Russian Chemical Bulletin, 72(10), 2513-2524. https://doi.org/10.1007/s11172-023-4054-0

Vancouver

Patrushev SS, Vasil’eva DO, Burova LG, Bondareva EA, Zakharova LN, Evstropov AN et al. Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers. Russian Chemical Bulletin. 2023 Oct;72(10):2513-2524. doi: 10.1007/s11172-023-4054-0

Author

Patrushev, S. S. ; Vasil’eva, D. O. ; Burova, L. G. et al. / Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers. In: Russian Chemical Bulletin. 2023 ; Vol. 72, No. 10. pp. 2513-2524.

BibTeX

@article{5b4288f45b0b4a7e99b9729a60f9290c,
title = "Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers",
abstract = "The reaction of isoalantolactone with primary amines or piperazine proceeds under mild conditions with high stereoselectivity to give 11,13-isoalantolactone dimers connected by an alkyldiamine or piperazine linker. The reaction of isoalantolactone with propargylamine hydrochloride afforded the corresponding 13-propargylamino-11,13-dihydroisoalantolactone or 13-propargylamino-N-bis(11,13-dihydroisoalantolactone). The synthesized propargylamines showed high activity in the Cu-catalyzed cycloaddition with organic azides. The newly synthesized compounds with a bis-eudesman structure were found to exhibit antibacterial activity against strains of Staphylococcus aureus, Bacillus cereus, and Escherichia coli.",
keywords = "1,2,3-triazoles, Michael reaction, antibacterial activity, azide-alkyne cycloaddition, azides, bis-eudesmanolides, diamines, isoalantolactone, sesquiterpenoids",
author = "Patrushev, {S. S.} and Vasil{\textquoteright}eva, {D. O.} and Burova, {L. G.} and Bondareva, {E. A.} and Zakharova, {L. N.} and Evstropov, {A. N.} and Shults, {E. E.}",
note = "This study was financially supported by the Russian Science Foundation (Project No. 23-73-00077). Публикация для корректировки.",
year = "2023",
month = oct,
doi = "10.1007/s11172-023-4054-0",
language = "English",
volume = "72",
pages = "2513--2524",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer Nature",
number = "10",

}

RIS

TY - JOUR

T1 - Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers

AU - Patrushev, S. S.

AU - Vasil’eva, D. O.

AU - Burova, L. G.

AU - Bondareva, E. A.

AU - Zakharova, L. N.

AU - Evstropov, A. N.

AU - Shults, E. E.

N1 - This study was financially supported by the Russian Science Foundation (Project No. 23-73-00077). Публикация для корректировки.

PY - 2023/10

Y1 - 2023/10

N2 - The reaction of isoalantolactone with primary amines or piperazine proceeds under mild conditions with high stereoselectivity to give 11,13-isoalantolactone dimers connected by an alkyldiamine or piperazine linker. The reaction of isoalantolactone with propargylamine hydrochloride afforded the corresponding 13-propargylamino-11,13-dihydroisoalantolactone or 13-propargylamino-N-bis(11,13-dihydroisoalantolactone). The synthesized propargylamines showed high activity in the Cu-catalyzed cycloaddition with organic azides. The newly synthesized compounds with a bis-eudesman structure were found to exhibit antibacterial activity against strains of Staphylococcus aureus, Bacillus cereus, and Escherichia coli.

AB - The reaction of isoalantolactone with primary amines or piperazine proceeds under mild conditions with high stereoselectivity to give 11,13-isoalantolactone dimers connected by an alkyldiamine or piperazine linker. The reaction of isoalantolactone with propargylamine hydrochloride afforded the corresponding 13-propargylamino-11,13-dihydroisoalantolactone or 13-propargylamino-N-bis(11,13-dihydroisoalantolactone). The synthesized propargylamines showed high activity in the Cu-catalyzed cycloaddition with organic azides. The newly synthesized compounds with a bis-eudesman structure were found to exhibit antibacterial activity against strains of Staphylococcus aureus, Bacillus cereus, and Escherichia coli.

KW - 1,2,3-triazoles

KW - Michael reaction

KW - antibacterial activity

KW - azide-alkyne cycloaddition

KW - azides

KW - bis-eudesmanolides

KW - diamines

KW - isoalantolactone

KW - sesquiterpenoids

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85176144195&origin=inward&txGid=282a283b46c2c1f0b685fd85a14f14b8

UR - https://www.mendeley.com/catalogue/32f9dd7a-2244-3771-9fc9-233e2b201bc5/

U2 - 10.1007/s11172-023-4054-0

DO - 10.1007/s11172-023-4054-0

M3 - Article

VL - 72

SP - 2513

EP - 2524

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 10

ER -

ID: 59548210