Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity

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Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity. / Rostovskii, Nikolai V. ; Koronatov, Alexander N. ; Sakharov, Pavel A. ; Agafonova, Anastasiya V. ; Novikov, Mikhail S. ; Khlebnikov, Alexander F. ; Rogacheva, Elizaveta V. ; Kraeva, Liudmila A. .

In: Organic and Biomolecular Chemistry, Vol. 18, No. 46, 14.12.2020, p. 9448-9460.

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

BibTeX

@article{c3118c771bcf4640a3d4c497eefb96e8,

title = "Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity",

abstract = "Azirine-containing dipeptides and depsipeptides with a wide range of substituents have been synthesized in high yields via the Passerini and Ugi multicomponent reactions (MCRs) using 2H-azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused aziridines,as well as pyrrole, imidazole, aziridine, and other derivatives, containing the dipeptide or depsipeptide moiety. The azirine-containing depsipeptides exhibit antibacterial activity against the ESKAPE pathogens, especially Gram-positive bacterial strains (E. faecium – MIC 16 μg mL−1, S. aureus – MIC 9 μg mL−1).",

author = "Rostovskii, {Nikolai V.} and Koronatov, {Alexander N.} and Sakharov, {Pavel A.} and Agafonova, {Anastasiya V.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.} and Rogacheva, {Elizaveta V.} and Kraeva, {Liudmila A.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

month = dec,

day = "14",

doi = "10.1039/d0ob02023k",

language = "English",

volume = "18",

pages = "9448--9460",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "46",

}

RIS

TY - JOUR

T1 - Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity

AU - Rostovskii, Nikolai V.

AU - Koronatov, Alexander N.

AU - Sakharov, Pavel A.

AU - Agafonova, Anastasiya V.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

AU - Rogacheva, Elizaveta V.

AU - Kraeva, Liudmila A.

PY - 2020/12/14

Y1 - 2020/12/14

N2 - Azirine-containing dipeptides and depsipeptides with a wide range of substituents have been synthesized in high yields via the Passerini and Ugi multicomponent reactions (MCRs) using 2H-azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused aziridines,as well as pyrrole, imidazole, aziridine, and other derivatives, containing the dipeptide or depsipeptide moiety. The azirine-containing depsipeptides exhibit antibacterial activity against the ESKAPE pathogens, especially Gram-positive bacterial strains (E. faecium – MIC 16 μg mL−1, S. aureus – MIC 9 μg mL−1).

AB - Azirine-containing dipeptides and depsipeptides with a wide range of substituents have been synthesized in high yields via the Passerini and Ugi multicomponent reactions (MCRs) using 2H-azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused aziridines,as well as pyrrole, imidazole, aziridine, and other derivatives, containing the dipeptide or depsipeptide moiety. The azirine-containing depsipeptides exhibit antibacterial activity against the ESKAPE pathogens, especially Gram-positive bacterial strains (E. faecium – MIC 16 μg mL−1, S. aureus – MIC 9 μg mL−1).

UR - http://www.scopus.com/inward/record.url?scp=85097423338&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/af74d579-2a3c-3bb0-bfc3-0a8e800a93fc/

U2 - 10.1039/d0ob02023k

DO - 10.1039/d0ob02023k

M3 - Article

VL - 18

SP - 9448

EP - 9460

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 46

ER -

ID: 70818631