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

Standard

Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis. / Krasavin, Mikhail; Lukin, Alexei; Vedekhina, Tatiana; Manicheva, Olga; Dogonadze, Marine; Vinogradova, Tatiana; Zabolotnykh, Natalia; Rogacheva, Elizaveta; Kraeva, Liudmila; Sharoyko, Vladimir ; Tennikova, Tatiana B.; Dar'in, Dmitry ; Sokolovich, Evgeny.

In: European Journal of Medicinal Chemistry, Vol. 166, 15.03.2019, p. 125-135.

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

BibTeX

@article{b5b86fdeca9d405bada5c7d67bf87284,

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

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.",

keywords = "Acylation, Antimycobacterial, ARPE-19 cell line, ESKAPE panel, Multidrug resistance, Nitrofuran antimicrobials, Non-specific toxicity, Periphery optimization, Prins reaction, Spirocycles, Tuberculosis",

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 Tennikova, {Tatiana B.} and Dmitry Dar'in and Evgeny Sokolovich",

note = "Krasavin, M., Lukin, A., Vedekhina, T., Manicheva, O., Dogonadze, M., Vinogradova, T., ... Sokolovich, E. (2019). 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, 166, 125-135. https://doi.org/10.1016/j.ejmech.2019.01.050",

year = "2019",

month = mar,

day = "15",

doi = "10.1016/j.ejmech.2019.01.050",

language = "English",

volume = "166",

pages = "125--135",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis

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, Tatiana B.

AU - Dar'in, Dmitry

AU - Sokolovich, Evgeny

N1 - Krasavin, M., Lukin, A., Vedekhina, T., Manicheva, O., Dogonadze, M., Vinogradova, T., ... Sokolovich, E. (2019). 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, 166, 125-135. https://doi.org/10.1016/j.ejmech.2019.01.050

PY - 2019/3/15

Y1 - 2019/3/15

N2 - 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.

AB - 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.

KW - Acylation

KW - Antimycobacterial

KW - ARPE-19 cell line

KW - ESKAPE panel

KW - Multidrug resistance

KW - Nitrofuran antimicrobials

KW - Non-specific toxicity

KW - Periphery optimization

KW - Prins reaction

KW - Spirocycles

KW - Tuberculosis

UR - http://www.scopus.com/inward/record.url?scp=85060535315&partnerID=8YFLogxK

U2 - 10.1016/j.ejmech.2019.01.050

DO - 10.1016/j.ejmech.2019.01.050

M3 - Article

AN - SCOPUS:85060535315

VL - 166

SP - 125

EP - 135

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -

ID: 39059313