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Molecules

, том 28 , издание 18 , страницы 6491

5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens

Elizaveta Rogacheva ¹

Ludmila A Kraeva ¹

Alexey Yu. Lukin ²

Lyubov Vinogradova ²

Kristina Komarova ²

Mikhail V Chudinov ²

M. A. Gureev ^{3, 4}

Evgeny Chupakhin ⁵

Скрыть аффилиации авторов Показать аффилиации авторов: 5 аффилиаций

Pasteur Institute of Epidemiology and Microbiology, Saint Petersburg 197101, Russia |

Lomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, Moscow 119454, Russia |

Laboratory of Bio- and Chemoinformatics, I. M. Sechenov First Moscow State Medical University, Moscow 119991, Russia |

⁴

Molecular Modeling Laboratory, HSE University, Saint-Petersburg 190121, Russia |

⁵

Institute of Living Systems, Immanuel Kant Baltic Federal University, Kaliningrad 236041, Russia |

Тип публикации: Journal Article

Дата публикации: 2023-09-07

MDPI

Molecules

scimago Q1

wos Q2

БС1

SJR: 0.865

CiteScore: 8.6

Impact factor: 4.6

ISSN: 14203049

DOI: 10.3390/molecules28186491

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PubMed ID: 37764267

Organic Chemistry

Drug Discovery

Physical and Theoretical Chemistry

Pharmaceutical Science

Molecular Medicine

Analytical Chemistry

Chemistry (miscellaneous)

Краткое описание

A series of eight 5-nitrofuran-tagged oxazolyl tetrahydropyrazolopyridines (THPPs) has been prepared in six stages with excellent regioselectivity. The testing of these compounds against pathogens of the ESKAPE panel showed a good activity of lead compound 1-(2-methoxyethyl)-5-(5-nitro-2-furoyl)-3-(1,3-oxazol-5-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c] pyridine (13g), which is superior to nitrofurantoin. These results confirmed the benefit of combining a THPP scaffold with a nitrofuran warhead. Certain structure–activity relationships were established in the course of this study which were rationalized by the induced-fit docking experiments in silico.

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Рогачева Елизавета

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33 публикации, 283 цитирования

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Санкт-Петербургский государственный университет

Санкт-Петербургский научно-исследовательский институт эпидемиологии и микробиологии им. Пастера

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Rogacheva E. et al. 5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens // Molecules. 2023. Vol. 28. No. 18. p. 6491.

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Rogacheva E., Kraeva L. A., Lukin A. Y., Vinogradova L., Komarova K., Chudinov M. V., Gureev M. A., Chupakhin E. 5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens // Molecules. 2023. Vol. 28. No. 18. p. 6491.

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TY - JOUR

DO - 10.3390/molecules28186491

UR - https://www.mdpi.com/1420-3049/28/18/6491

TI - 5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens

T2 - Molecules

AU - Rogacheva, Elizaveta

AU - Kraeva, Ludmila A

AU - Lukin, Alexey Yu.

AU - Vinogradova, Lyubov

AU - Komarova, Kristina

AU - Chudinov, Mikhail V

AU - Gureev, M. A.

AU - Chupakhin, Evgeny

PY - 2023

DA - 2023/09/07

PB - MDPI

SP - 6491

IS - 18

VL - 28

PMID - 37764267

SN - 1420-3049

ER -

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@article{2023_Rogacheva,

author = {Elizaveta Rogacheva and Ludmila A Kraeva and Alexey Yu. Lukin and Lyubov Vinogradova and Kristina Komarova and Mikhail V Chudinov and M. A. Gureev and Evgeny Chupakhin},

title = {5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens},

journal = {Molecules},

year = {2023},

volume = {28},

publisher = {MDPI},

month = {sep},

url = {https://www.mdpi.com/1420-3049/28/18/6491},

number = {18},

pages = {6491},

doi = {10.3390/molecules28186491}

}

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Rogacheva, Elizaveta, et al. “5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens.” Molecules, vol. 28, no. 18, Sep. 2023, p. 6491. https://www.mdpi.com/1420-3049/28/18/6491.