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dc.contributor.authorZapol'skii, Viktor A
dc.contributor.authorBilitewski, Ursula
dc.contributor.authorKupiec, Sören R
dc.contributor.authorRamming, Isabell
dc.contributor.authorKaufmann, Dieter E
dc.date.accessioned2020-08-03T13:16:56Z
dc.date.available2020-08-03T13:16:56Z
dc.date.issued2020-06-21
dc.identifier.citationMolecules. 2020;25(12):2863. Published 2020 Jun 21. doi:10.3390/molecules25122863.en_US
dc.identifier.pmid32575902
dc.identifier.doi10.3390/molecules25122863
dc.identifier.urihttp://hdl.handle.net/10033/622377
dc.description.abstractSubstituted 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.en_US
dc.language.isoenen_US
dc.publisherMDPIen_US
dc.rightsAttribution-NonCommercial-ShareAlike 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.subjectheterocyclizationen_US
dc.subjectmedicinal chemistryen_US
dc.subjectnitrogen heterocyclesen_US
dc.subjectnucleophilic substitutionen_US
dc.subjectpolyhalonitrobutadienesen_US
dc.titlePolyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds.en_US
dc.typeArticleen_US
dc.identifier.eissn1420-3049
dc.contributor.departmentHZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.en_US
dc.identifier.journalMolecules (Basel, Switzerland)en_US
dc.source.volume25
dc.source.issue12
refterms.dateFOA2020-08-03T13:16:57Z
dc.source.journaltitleMolecules (Basel, Switzerland)
dc.source.countrySwitzerland


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