European Journal of Medicinal Chemistry

, volume 166 , pages 125-135

Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis

Mikhail Krasavin ¹

Alexei Lukin ²

Tatiana Vedekhina ²

Olga Manicheva ³

Marine Dogonadze ³

Tatiana Vinogradova ³

Natalia Zabolotnykh ³

Elizaveta Rogacheva ⁴

Liudmila Kraeva ⁴

Vladimir Sharoyko ¹

T. B. Tennikova ¹

Dmitry Dar’in ¹

Evgeny Sokolovich ^{3, 5}

Hide authors affiliations Show authors affiliations: 5 affiliations

Saint Petersburg State University , Saint Petersburg , 199034 Russian Federation. |

Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, Moscow, 119571, Russian Federation. |

Saint Petersburg Research Institute of Phthisiopulmonology, 2-4 Ligovsky Prospekt, Saint Petersburg, 191036, Russian Federation. |

⁴

Pasteur Institute of Epidemiology and Microbiology, 14 Mira Street, Saint Petersburg, 197101, Russian Federation |

⁵

Saint Petersburg State University, Saint Petersburg, 199034, Russian Federation |

Publication type: Journal Article

Publication date: 2019-03-01

Elsevier

European Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR: 1.142

CiteScore: 11.3

Impact factor: 5.9

ISSN: 02235234, 17683254

DOI: 10.1016/j.ejmech.2019.01.050

Copy DOI

PubMed ID: 30703656

Organic Chemistry

Drug Discovery

General Medicine

Pharmacology

Abstract

A selectively antimycobacterial compound belonging to the nitrofuran class of antimicrobials has been developed via conjugation of the nitrofuran moiety to a series of spirocyclic piperidines through an amide linkage. It proved to have comparable activity against drug-sensitive (H37Rv) strain as well as multidrug-resistant, patient-derived strains of Mycobacterium tuberculosis. The compound is druglike, showed no appreciable cytotoxicity toward human retinal pigment epithelial cell line ARPE-19 in concentrations up to 100 μM and displayed low toxicity when evaluated in mice.

Found

6 citations

Rogacheva Elizaveta

🥼 🤝

33 publications, 289 citations

h-index: 11

ITMO University

Saint Petersburg State University

Saint-Petersburg Pasteur Institute

Research interests

Antibiotic resistance

Antibiotics

Bacteriophages

Microbiology

5 citations

Gureev Maxim

PhD in Chemistry, associate professor

58 publications, 727 citations

h-index: 13

National Research University Higher School of Economics

Institute of Cytology of the Russian Academy of Sciences

The structure of proteins

3 citations

Baykov Sergey

🥼 🤝

PhD in Chemistry

99 publications, 1 360 citations, 16 reviews

h-index: 21

Saint Petersburg State University

2 citations

Bakulina Olga

66 publications, 517 citations, 11 reviews

h-index: 13

Saint Petersburg State University

1 citation

Levin Oleg

DSc in Chemistry

145 publications, 1 905 citations, 115 reviews

h-index: 25

Sirius University of Science and Technology

Saint Petersburg State University

Research interests

Electrochemistry

Materials Science

1 citation

Kinzhalov Mikhail

🥼 🤝

DSc in Chemistry, associate professor

98 publications, 1 926 citations

h-index: 28

National Research Tomsk Polytechnic University

Saint Petersburg State University

Research interests

Coordination Chemistry

Non-covalent Interactions

Organic Chemistry

Organometallic Chemistry

1 citation

Shetnev Anton

PhD in Chemistry

79 publications, 774 citations

h-index: 15

Moscow Institute of Physics and Technology

Yaroslavl State Medical University

Yaroslavl State Pedagogical University

1 citation

Kotlyarova Valentina

4 publications, 22 citations

h-index: 4

Yaroslavl State Technical University

Yaroslavl State Pedagogical University

Research interests

Heterocyclic compounds

Organic synthesis

1 citation

Islamov Daut

PhD

168 publications, 1 577 citations

h-index: 20

Kazan Scientific Center of the Russian Academy of Sciences

Research interests

X-ray diffraction analysis

1 citation

Sokolovich Evgenii

DSc, professor

43 publications, 151 citations

h-index: 6

National Medical Research Center of Phthisiopulmonology and Infectious Diseases

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GOST |

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GOST Copy

Krasavin M. et al. Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis // European Journal of Medicinal Chemistry. 2019. Vol. 166. pp. 125-135.

GOST all authors (up to 50) Copy

Krasavin M., Lukin A., Vedekhina T., Manicheva O., Dogonadze M., Vinogradova T., Zabolotnykh N., Rogacheva E., Kraeva L., Sharoyko V., Tennikova T. B., Dar’in D., Sokolovich E. Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis // European Journal of Medicinal Chemistry. 2019. Vol. 166. pp. 125-135.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/j.ejmech.2019.01.050

UR - https://doi.org/10.1016/j.ejmech.2019.01.050

TI - Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis

T2 - European Journal of Medicinal Chemistry

AU - Krasavin, Mikhail

AU - Lukin, Alexei

AU - Vedekhina, Tatiana

AU - Manicheva, Olga

AU - Dogonadze, Marine

AU - Vinogradova, Tatiana

AU - Zabolotnykh, Natalia

AU - Rogacheva, Elizaveta

AU - Kraeva, Liudmila

AU - Sharoyko, Vladimir

AU - Tennikova, T. B.

AU - Dar’in, Dmitry

AU - Sokolovich, Evgeny

PY - 2019

DA - 2019/03/01

PB - Elsevier

SP - 125-135

VL - 166

PMID - 30703656

SN - 0223-5234

SN - 1768-3254

ER -

BibTex

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Krasavin,

author = {Mikhail Krasavin and Alexei Lukin and Tatiana Vedekhina and Olga Manicheva and Marine Dogonadze and Tatiana Vinogradova and Natalia Zabolotnykh and Elizaveta Rogacheva and Liudmila Kraeva and Vladimir Sharoyko and T. B. Tennikova and Dmitry Dar’in and Evgeny Sokolovich},

title = {Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis},

journal = {European Journal of Medicinal Chemistry},

year = {2019},

volume = {166},

publisher = {Elsevier},

month = {mar},

url = {https://doi.org/10.1016/j.ejmech.2019.01.050},

pages = {125--135},

doi = {10.1016/j.ejmech.2019.01.050}

}

Publisher

Elsevier

Journal

European Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR

1.142

CiteScore

11.3

Impact factor

5.9

ISSN

02235234 (Print)

17683254 (Electronic)

Labs

CCP MICROS. COLLECTION OF MICROORGANISMS OF THE PASTEUR RESEARCH INSTITUTE OF EPIDEMIOLOGY AND MICROBIOLOGY

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