New approach to 5-arylamino-4-(5-aryloxyfuran-2-yl)pyrimidines: synthesis and antibacterial activity

Verbitskiy, Egor V.; Baskakova, Svetlana A.; Rusinov, Gennady L.; Charushin, Valery N.

doi:10.1007/s11172-021-3170-y

Cited by 6 publications

(1 citation statement)

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“…Although numerous various nitro heterocyclic moieties have manifested themselves as a source of antibacterial leads [ 18 ], the conjugation of classical nitrofurans to various heterocyclic motifs not only can render these compounds generally non-cytotoxic [ 19 ] but also can direct their activity towards a specific type of antibacterial property, that does not affect the microbiome at large [ 20 ]. Moreover, nitrofurans proved to be versatile synthetic intermediates en route to other furan derivatives that were accessed via nucleophilic substitution of the nitro group [ 21 ]. A few years ago, we [ 22 , 23 ] and others [ 24 ] have already explored this strategy successfully by conjugating privileged [ 25 ] aminoalkylimidazoles, 1,2,4-oxadiazoles, and pyrimidines to 5-nitrofuranoyl moiety, which resulted in compounds that were found to be antibacterial.…”

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confidence: 99%

Novel 5-Nitrofuran-Tagged Imidazo-Fused Azines and Azoles Amenable by the Groebke–Blackburn–Bienaymé Multicomponent Reaction: Activity Profile against ESKAPE Pathogens and Mycobacteria

et al. 2022

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A chemically diverse set of 13 5-nitrofuran-tagged heterocyclic compounds has been prepared via the Groebke–Blackburn–Bienaymé multicomponent reaction. The testing of these compounds 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 excellent profile 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 convenient synthesis warrant further pre-clinical development. Certain structure-activity relationships were established in the course of this study which were rationalized by the flexible docking experiments in silico. The assessment of antitubercular potential of the compounds synthesized against drug sensitive H37v strain of Mycobacterium tuberculosis revealed little potential of the imidazo-fused products of the Groebke–Blackburn–Bienaymé multicomponent reaction as chemotherapeutic agents against this pathogen.

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