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Novel 5-nitrofuran-tagged imidazo-fused azines and azoles amenable by the Groebke–Blackburn–Bienaymé multicomponent reaction: activity profile against ESKAPE pathogens and mycobacteria. / Sapegin , Alexander ; Rogacheva, Elizaveta; Lyudmila Kraeva, Lyudmila Kraeva; Gureev, Maxim ; Dogonadze , Marine ; Vinogradova, Tatiana ; Yablonsky, Petr ; Balalaie, Saeed; Baykov , Sergey V. ; Krasavin, Mikhail .

In: Biomedicines, Vol. 10, No. 9, 2203, 06.09.2022.

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

Harvard

Sapegin , A, Rogacheva, E, Lyudmila Kraeva, LK, Gureev, M, Dogonadze , M, Vinogradova, T, Yablonsky, P, Balalaie, S, Baykov , SV & Krasavin, M 2022, 'Novel 5-nitrofuran-tagged imidazo-fused azines and azoles amenable by the Groebke–Blackburn–Bienaymé multicomponent reaction: activity profile against ESKAPE pathogens and mycobacteria', Biomedicines, vol. 10, no. 9, 2203.

APA

Sapegin , A., Rogacheva, E., Lyudmila Kraeva, L. K., Gureev, M., Dogonadze , M., Vinogradova, T., Yablonsky, P., Balalaie, S., Baykov , S. V., & Krasavin, M. (2022). Novel 5-nitrofuran-tagged imidazo-fused azines and azoles amenable by the Groebke–Blackburn–Bienaymé multicomponent reaction: activity profile against ESKAPE pathogens and mycobacteria. Biomedicines, 10(9), [2203].

Vancouver

Sapegin A, Rogacheva E, Lyudmila Kraeva LK, Gureev M, Dogonadze M, Vinogradova T et al. Novel 5-nitrofuran-tagged imidazo-fused azines and azoles amenable by the Groebke–Blackburn–Bienaymé multicomponent reaction: activity profile against ESKAPE pathogens and mycobacteria. Biomedicines. 2022 Sep 6;10(9). 2203.

Author

Sapegin , Alexander ; Rogacheva, Elizaveta ; Lyudmila Kraeva, Lyudmila Kraeva ; Gureev, Maxim ; Dogonadze , Marine ; Vinogradova, Tatiana ; Yablonsky, Petr ; Balalaie, Saeed ; Baykov , Sergey V. ; Krasavin, Mikhail . / Novel 5-nitrofuran-tagged imidazo-fused azines and azoles amenable by the Groebke–Blackburn–Bienaymé multicomponent reaction: activity profile against ESKAPE pathogens and mycobacteria. In: Biomedicines. 2022 ; Vol. 10, No. 9.

BibTeX

@article{4eab517cd4ab477c9345345c92c39a89,
title = "Novel 5-nitrofuran-tagged imidazo-fused azines and azoles amenable by the Groebke–Blackburn–Bienaym{\'e} multicomponent reaction: activity profile against ESKAPE pathogens and mycobacteria",
abstract = ": A chemically diverse set of 13 5-nitrofuran-tagged heterocyclic compounds has been prepared via the Groebke–Blackburn–Bienaym{\'e} multicomponent reaction. The testing of thesecompounds against the so-called ESKAPE panel of pathogens identified an apparent lead compound—N-cyclohexyl-2-(5-nitrofuran-2-yl)imidazo[1,2-a]pyridine-3-amine (4a)—which showed an excellentprofile against Enterobacter cloacae, Staphylococcus aureus, Klebsiella pneumoniae, and Enterococcus faecalis(MIC 0.25, 0.06, 0.25 and 0.25 µg/mL, respectively). Its antibacterial profile and practically convenientsynthesis warrant further pre-clinical development. Certain structure-activity relationships wereestablished in the course of this study which were rationalized by the flexible docking experimentsin silico. The assessment of antitubercular potential of the compounds synthesized against drugsensitive H37v strain of Mycobacterium tuberculosis revealed little potential of the imidazo-fusedproducts of the Groebke–Blackburn–Bienaym{\'e} multicomponent reaction as chemotherapeutic agentsagainst this pathogen.",
keywords = "Groebke–Blackburn–Bienaym{\'e} multicomponent reaction, imidazo-fused azines and azoles, 5-nitrofurancarboxaldehyde, ESKAPE pathogens, antibacterial testing, antimycobacterial activity, flexible docking, strained ligand-protein interactions",
author = "Alexander Sapegin and Elizaveta Rogacheva and {Lyudmila Kraeva}, {Lyudmila Kraeva} and Maxim Gureev and Marine Dogonadze and Tatiana Vinogradova and Petr Yablonsky and Saeed Balalaie and Baykov, {Sergey V.} and Mikhail Krasavin",
note = " Sapegin, A.; Rogacheva, E.; Kraeva, L.; Gureev, M.; Dogonadze, M.; Vinogradova, T.; Yablonsky, P.; Balalaie, S.; Baykov, S.V.; Krasavin, M. Novel 5-Nitrofuran-Tagged Imidazo-Fused Azines and Azoles Amenable by the Groebke–Blackburn–Bienaym{\'e} Multicomponent Reaction: Activity Profile against ESKAPE Pathogens and Mycobacteria. Biomedicines 2022, 10, 2203. https://doi.org/10.3390/biomedicines10092203 ",
year = "2022",
month = sep,
day = "6",
language = "English",
volume = "10",
journal = "Biomedicines",
issn = "2227-9059",
publisher = "MDPI AG",
number = "9",

}

RIS

TY - JOUR

T1 - Novel 5-nitrofuran-tagged imidazo-fused azines and azoles amenable by the Groebke–Blackburn–Bienaymé multicomponent reaction: activity profile against ESKAPE pathogens and mycobacteria

AU - Sapegin , Alexander

AU - Rogacheva, Elizaveta

AU - Lyudmila Kraeva, Lyudmila Kraeva

AU - Gureev, Maxim

AU - Dogonadze , Marine

AU - Vinogradova, Tatiana

AU - Yablonsky, Petr

AU - Balalaie, Saeed

AU - Baykov , Sergey V.

AU - Krasavin, Mikhail

N1 - Sapegin, A.; Rogacheva, E.; Kraeva, L.; Gureev, M.; Dogonadze, M.; Vinogradova, T.; Yablonsky, P.; Balalaie, S.; Baykov, S.V.; Krasavin, M. Novel 5-Nitrofuran-Tagged Imidazo-Fused Azines and Azoles Amenable by the Groebke–Blackburn–Bienaymé Multicomponent Reaction: Activity Profile against ESKAPE Pathogens and Mycobacteria. Biomedicines 2022, 10, 2203. https://doi.org/10.3390/biomedicines10092203

PY - 2022/9/6

Y1 - 2022/9/6

N2 - : A chemically diverse set of 13 5-nitrofuran-tagged heterocyclic compounds has been prepared via the Groebke–Blackburn–Bienaymé multicomponent reaction. The testing of thesecompounds against the so-called ESKAPE panel of pathogens identified an apparent lead compound—N-cyclohexyl-2-(5-nitrofuran-2-yl)imidazo[1,2-a]pyridine-3-amine (4a)—which showed an excellentprofile against Enterobacter cloacae, Staphylococcus aureus, Klebsiella pneumoniae, and Enterococcus faecalis(MIC 0.25, 0.06, 0.25 and 0.25 µg/mL, respectively). Its antibacterial profile and practically convenientsynthesis warrant further pre-clinical development. Certain structure-activity relationships wereestablished in the course of this study which were rationalized by the flexible docking experimentsin silico. The assessment of antitubercular potential of the compounds synthesized against drugsensitive H37v strain of Mycobacterium tuberculosis revealed little potential of the imidazo-fusedproducts of the Groebke–Blackburn–Bienaymé multicomponent reaction as chemotherapeutic agentsagainst this pathogen.

AB - : A chemically diverse set of 13 5-nitrofuran-tagged heterocyclic compounds has been prepared via the Groebke–Blackburn–Bienaymé multicomponent reaction. The testing of thesecompounds against the so-called ESKAPE panel of pathogens identified an apparent lead compound—N-cyclohexyl-2-(5-nitrofuran-2-yl)imidazo[1,2-a]pyridine-3-amine (4a)—which showed an excellentprofile against Enterobacter cloacae, Staphylococcus aureus, Klebsiella pneumoniae, and Enterococcus faecalis(MIC 0.25, 0.06, 0.25 and 0.25 µg/mL, respectively). Its antibacterial profile and practically convenientsynthesis warrant further pre-clinical development. Certain structure-activity relationships wereestablished in the course of this study which were rationalized by the flexible docking experimentsin silico. The assessment of antitubercular potential of the compounds synthesized against drugsensitive H37v strain of Mycobacterium tuberculosis revealed little potential of the imidazo-fusedproducts of the Groebke–Blackburn–Bienaymé multicomponent reaction as chemotherapeutic agentsagainst this pathogen.

KW - Groebke–Blackburn–Bienaymé multicomponent reaction

KW - imidazo-fused azines and azoles

KW - 5-nitrofurancarboxaldehyde

KW - ESKAPE pathogens

KW - antibacterial testing

KW - antimycobacterial activity

KW - flexible docking

KW - strained ligand-protein interactions

UR - https://pubmed.ncbi.nlm.nih.gov/36140307/

M3 - Article

VL - 10

JO - Biomedicines

JF - Biomedicines

SN - 2227-9059

IS - 9

M1 - 2203

ER -

ID: 100251799