5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens-Reference-Cited by-同舟云学术

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

Published:2023-09-07 Issue:18 Volume:28 Page:6491
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Rogacheva Elizaveta¹,Kraeva Lyudmila¹^ORCID,Lukin Alexey²^ORCID,Vinogradova Lyubov²,Komarova Kristina²,Chudinov Mikhail²^ORCID,Gureev Maxim³⁴^ORCID,Chupakhin Evgeny⁵^ORCID

Affiliation:

1. Pasteur Institute of Epidemiology and Microbiology, Saint Petersburg 197101, Russia

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

3. 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

Abstract

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.

Funder

Ministry of Education and Science of Russia

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

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

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