Organic and Biomolecular Chemistry

, volume 18 , issue 46 , pages 9448-9460

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

Nikolai V Rostovskii ^{1, 2, 3, 4, 5}

Aleksandr Koronatov ^{1, 2, 3, 4, 5}

Pavel A Sakharov ^{1, 2, 3, 4, 5}

Anastasiya V Agafonova ^{1, 2, 3, 4, 5}

Mikhail S. Novikov ^{1, 2, 3, 4, 5}

Alexander F Khlebnikov ^{1, 2, 3, 4, 5}

Elizaveta V Rogacheva ^{1, 2, 3, 4, 5, 6, 7}

Liudmila A Kraeva ^{4, 5, 6, 7}

Hide authors affiliations Show authors affiliations: 7 affiliations

Saint Petersburg State University, Institute of Chemistry, 7/9 Universitetskaya nab., Saint Petersburg, Russia |

Saint Petersburg State University |

Institute of Chemistry

⁴

Saint Petersburg |

⁵

Russia |

⁶

Pasteur Institute of Epidemiology and Microbiology, 14 Mira Street, Saint Petersburg, Russia |

⁷

Pasteur Institute of Epidemiology and Microbiology |

Publication type: Journal Article

Publication date: 2020-11-05

Royal Society of Chemistry (RSC)

Organic and Biomolecular Chemistry

scimago Q2

wos Q2

SJR: 0.600

CiteScore: 5.2

Impact factor: 2.7

ISSN: 14770520, 14770539

DOI: 10.1039/d0ob02023k

Copy DOI

PubMed ID: 33170920

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

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).

Found

6 citations

Novikov Mikhail

DSc in Chemistry, associate professor

216 publications, 4 151 citations, 54 reviews

h-index: 33

Saint Petersburg State University

2 citations

Aksenov Aleksandr

🥼 🤝

DSc in Chemistry, professor

243 publications, 2 163 citations, 15 reviews

h-index: 24

North Caucasus Federal University

Research interests

Medicinal Chemistry

Organic Chemistry

2 citations

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 707 citations

h-index: 30

Ural Federal University

1 citation

Beloglazkina Elena

DSc in Chemistry, professor

296 publications, 3 214 citations, 11 reviews

h-index: 29

Lomonosov Moscow State University

1 citation

Yaremenko Ivan

PhD in Chemistry

59 publications, 1 559 citations, 5 reviews

h-index: 24

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

1 citation

Gorbunova Yuliya

DSc in Chemistry, professor, full member of the Russian Academy of Sciences

284 publications, 4 382 citations, 65 reviews

h-index: 34

Lomonosov Moscow State University

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Lanthanides

Supramolecular chemistry

Tetrapyrrolic compounds

1 citation

Volcho Konstantin

DSc in Chemistry, professor of the Russian Academy of Sciences

279 publications, 3 885 citations, 65 reviews

h-index: 31

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

1 citation

Danilkina Natalia

43 publications, 617 citations

h-index: 14

Saint Petersburg State University

Research interests

Bioorganic chemistry

Click chemistry

Heterocyclic compounds

Medicinal Chemistry

Organic Chemistry

1 citation

Osipov Sergey

DSc in Chemistry

138 publications, 2 725 citations, 3 reviews

h-index: 29

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Gazizov Almir

🥼

DSc in Chemistry

157 publications, 879 citations, 23 reviews

h-index: 14

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Heterocyclic compounds

Organic Chemistry

Organophosphorus chemistry

1 citation

Karasik Andrey

DSc in Chemistry, professor, associate member of the Russian Academy of Sciences

224 publications, 2 591 citations

h-index: 26

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Luminescence

Phosphorus ligands

1 citation

Dotsenko Viktor

DSc in Chemistry, professor

244 publications, 2 706 citations, 2 reviews

h-index: 22

North Caucasus Federal University

Kuban State University

Research interests

Active methylene compounds

Biological activity

Heterocyclic compounds

Malononitrile

Selenoamides

Thioamides

1 citation

Zagidullin Almaz

🥼 🤝

PhD in Chemistry

81 publications, 876 citations

h-index: 17

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials

Coordination chemistry of phosphorus

Organoelement chemistry

Organophosphorus chemistry

Synthesis of chiral phosphorus-containing ligands

1 citation

Ilkin Vladimir

PhD in Chemistry

16 publications, 179 citations

h-index: 7

Ural Federal University

Research interests

Catalysis

Heterocyclic compounds

Organic Chemistry

Synthetic Organic Chemistry

1 citation

Ivleva Elena

67 publications, 465 citations

h-index: 12

Samara State Technical University

Research interests

Organic Chemistry

Organic synthesis

1 citation

Krylov Igor

PhD in Chemistry

78 publications, 1 876 citations, 18 reviews

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Green chemistry

Organic Chemistry

Organic electrochemistry

Organic synthesis

Photochemistry

Plant protection

1 citation

Tikhomirov Alexander

🥼 🤝

DSc in Chemistry, associate professor

59 publications, 910 citations

h-index: 17

Mendeleev University of Chemical Technology of Russia

Gause Institute of New Antibiotics

Research interests

Medicinal Chemistry

1 citation

Ivanov Andrey

54 publications, 526 citations

h-index: 12

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

1 citation

Buev Evgeny

PhD in Chemistry

31 publications, 337 citations, 2 reviews

h-index: 9

Ural Federal University

Research interests

Chemistry of nitrogen-containing heterocycles

Organic Chemistry

Organic synthesis

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GOST |

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GOST Copy

Rostovskii N. V. et al. Azirine-containing dipeptides and depsipeptides: Synthesis, transformations and antibacterial activity // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 46. pp. 9448-9460.

GOST all authors (up to 50) Copy

Rostovskii N. V., Koronatov A., Sakharov P. A., Agafonova A. V., Novikov M. S., Khlebnikov A. F., Rogacheva E. V., Kraeva L. A. Azirine-containing dipeptides and depsipeptides: Synthesis, transformations and antibacterial activity // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 46. pp. 9448-9460.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/d0ob02023k

UR - https://xlink.rsc.org/?DOI=D0OB02023K

TI - Azirine-containing dipeptides and depsipeptides: Synthesis, transformations and antibacterial activity

T2 - Organic and Biomolecular Chemistry

AU - Rostovskii, Nikolai V

AU - Koronatov, Aleksandr

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

DA - 2020/11/05

PB - Royal Society of Chemistry (RSC)

SP - 9448-9460

IS - 46

VL - 18

PMID - 33170920

SN - 1477-0520

SN - 1477-0539

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2020_Rostovskii,

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

title = {Azirine-containing dipeptides and depsipeptides: Synthesis, transformations and antibacterial activity},

journal = {Organic and Biomolecular Chemistry},

year = {2020},

volume = {18},

publisher = {Royal Society of Chemistry (RSC)},

month = {nov},

url = {https://xlink.rsc.org/?DOI=D0OB02023K},

number = {46},

pages = {9448--9460},

doi = {10.1039/d0ob02023k}

}

MLA

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MLA Copy

Rostovskii, Nikolai V., et al. “Azirine-containing dipeptides and depsipeptides: Synthesis, transformations and antibacterial activity.” Organic and Biomolecular Chemistry, vol. 18, no. 46, Nov. 2020, pp. 9448-9460. https://xlink.rsc.org/?DOI=D0OB02023K.

Publisher

Royal Society of Chemistry (RSC)

Journal

Organic and Biomolecular Chemistry

scimago Q2

wos Q2

SJR

0.600

CiteScore

5.2

Impact factor

2.7

ISSN

14770520 (Print)

14770539 (Electronic)

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