Sciact
  • EN
  • RU

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

Journal Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171
Output data Year: 2023, Volume: 72, Number: 10, Pages: 2513-2524 Pages count : 12 DOI: 10.1007/s11172-023-4054-0
Tags sesquiterpenoids isoalantolactone bis-eudesmanolides diamines azides 1,2,3-triazoles Michael reaction azide-alkyne cycloaddition antibacterial activity
Authors Patrushev S.S. 1,2 , Vasil’eva D.O. 1 , Burova L.G. 3 , Bondareva E.A. 3 , Zakharova L.N. 3 , Evstropov A.N. 3 , Shults E.E. 1
Affiliations
1 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
2 Novosibirsk State University
3 Novosibirsk State Medical University

Funding (1)

1 Российский Научный Фонд 23-73-00077

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.
Cite: Patrushev S.S. , Vasil’eva D.O. , Burova L.G. , Bondareva E.A. , Zakharova L.N. , Evstropov A.N. , Shults E.E.
Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers
Russian Chemical Bulletin. 2023. V.72. N10. P.2513-2524. DOI: 10.1007/s11172-023-4054-0 WOS Scopus РИНЦ
ArticleLinkType.TRANSLATED_TO_ORIGINAL: Патрушев С.С. , Васильева Д.О. , Бурова Л.Г. , Бондарева Е.А. , Захарова Л.Н. , Евстропов А.Н. , Шульц Э.Э.
Синтез и оценка антибактериальной активности бис-эудесманолидов с азотсодержащими линкерами
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2023. Т.72. №10. С.2513-2524.
Dates:
Submitted: May 15, 2023
Accepted: Jul 7, 2023
Published print: Nov 11, 2023
Identifiers:
Web of science WOS:001103056900029
Scopus 2-s2.0-85176144195
Elibrary 64003783
OpenAlex W4388587032
Altmetrics: