Transformations of 5‐nitropyrimidines

Riabova, Olga; Makarov, Vadim; Граник, В. Г.; Párkányi, Cyril

doi:10.1002/jhet.5570450301

Cited by 9 publications

(1 citation statement)

References 89 publications

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“…The assumed mechanism for the formation of pyrimidines 27 has been presented in the literature [33]. 5-Nitro-substituted pyrimidines are interesting precursors for the synthesis of a wide range of poly-substituted pyrimidines and other heterocyclic systems with potential biological activity [34]. Among numerous applications, some examples are noteworthy: cytotoxic activity is documented [35,36] as well as the potential to inactivate the human DNA repair process [37].…”

Section: Pyrimidinesmentioning

confidence: 99%

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Zapol’skii

Bilitewski²,

Kupiec³

et al. 2020

Molecules

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Substituted nitrogen heterocycles are structural key units in many important pharmaceuticals. A new synthetic approach towards heterocyclic compounds displaying antibacterial activity against Staphylococcus aureus or cytotoxic activity has been developed. The selective synthesis of a series of 64 new N-heterocycles from the three nitrobutadienes 2-nitroperchloro-1,3-butadiene, 4-bromotetrachloro-2-nitro-1,3-butadiene and (Z)-1,1,4-trichloro-2,4-dinitrobuta-1,3-diene proved feasible. Their reactions with N-, O- and S-nucleophiles provide rapid access to push-pull substituted benzoxazolines, benzimidazolines, imidazolidines, thiazolidinones, pyrazoles, pyrimidines, pyridopyrimidines, benzoquinolines, isothiazoles, dihydroisoxazoles, and thiophenes with unique substitution patterns. Antibacterial activities of 64 synthesized compounds were examined. Additionally, seven compounds (thiazolidinone, nitropyrimidine, indole, pyridopyrimidine, and thiophene derivatives) exhibited a significant cytotoxicity with IC50-values from 1.05 to 20.1 µM. In conclusion, it was demonstrated that polyhalonitrobutadienes have an interesting potential as structural backbones for a variety of highly functionalized, pharmaceutically active heterocycles.

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Section: Pyrimidinesmentioning

confidence: 99%

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Zapol’skii

Bilitewski²,

Kupiec³

et al. 2020

Molecules

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ChemInform Abstract: Transformations of 5‐Nitropyrimidines

et al. 2008

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Alkoxy‐5‐nitrosopyrimidines: Useful Building Block for the Generation of Biologically Active Compounds

et al. 2010

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Several alkoxy‐5‐nitrosopyrimidines were synthesised and high regioselective and sequential nucleophilic aromatic substitution of methoxy groups in 2‐amino‐4,6‐dimethoxy‐5‐nitrosopyrimidine was observed. The approach was applied to the synthesis of valuable polyfunctionalised aminopyrimidines capable of mimicking fused heterobicyclic derivatives of biological interest. In addition, new compounds were evaluated as antivirals and their usefulness as synthetic intermediates was demonstrated.

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Transformations of 5‐nitropyrimidines

Cited by 9 publications

References 89 publications

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

ChemInform Abstract: Transformations of 5‐Nitropyrimidines

Alkoxy‐5‐nitrosopyrimidines: Useful Building Block for the Generation of Biologically Active Compounds

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