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

Elizaveta Rogacheva; Lyudmila Kraeva; Alexey Lukin; Lyubov Vinogradova; Kristina Komarova; Mikhail Chudinov; Maxim Gureev; Evgeny Chupakhin

doi:10.20944/preprints202308.0048.v1

A peer-reviewed article of this Preprint also exists.

Rogacheva, E.; Kraeva, L.; Lukin, A.; Vinogradova, L.; Komarova, K.; Chudinov, M.; Gureev, M.; Chupakhin, E. 5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens. Molecules 2023, 28, 6491. Rogacheva, E.; Kraeva, L.; Lukin, A.; Vinogradova, L.; Komarova, K.; Chudinov, M.; Gureev, M.; Chupakhin, E. 5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens. Molecules 2023, 28, 6491.

Abstract

A series of eight 5-nitrofuran-tagged oxazolyl tetrahydropyrazolopyridines (THPP’s) has been prepared in six stages with excellent regioselectivity. The testing of these compounds against pathogens of 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.

Keywords

tetrahydropyrazolopyridine; 5-nitrofuran derivatives; ESKAPE pathogens; antibacterial testing; nitroreductase; flexible docking; strained ligand-protein interactions

Subject

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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

Abstract

Keywords

Subject

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