Phosphorus-nitrogen compounds. Part 42. The comparative syntheses of 2-cis-4-ansa(N/O) and spiro(N/O) cyclotetraphosphazene derivatives: spectroscopic and crystallographic characterization, antituberculosis and cytotoxic activity studies

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dc.contributor.authorBinici, Arzu
dc.contributor.authorOkumus, Aytug
dc.contributor.authorElmas, Gamze
dc.contributor.authorKilic, Zeynel
dc.contributor.authorRamazanoglu, Nagehan
dc.contributor.authorAcik, Leyla
dc.contributor.authorHokelek, Tuncer
dc.date.accessioned2020-06-25T18:34:04Z
dc.date.available2020-06-25T18:34:04Z
dc.date.issued2019
dc.departmentKırıkkale Üniversitesi
dc.descriptionokumus, aytug/0000-0002-2169-5695;
dc.description.abstractThe reaction of N4P4Cl8 (1) with one equimolar amount of the sodium salt of an N/O donor-type bidentate ligand (2) afforded two kinds of derivatives, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa- (2,4-ansa; 3) and mono-ferrocenyl-spiro- (spiro; 4) hexachlorocyclotetraphosphazenes. The reaction yield (35%) of 4 was significantly larger than that of 3 (14%). The 2,4-ansa compound (3) was reacted with excess secondary amines to produce 2-cis-4-dichloro-ansa-cyclotetraphosphazenes (3a-3d). On the other hand, the spiro compound (4) gave fully substituted mono-ferrocenyl-spiro-cyclotetraphosphazenes (4a-4d) with excess monoamines as well. The tetrameric phosphazene derivatives were characterized by ESI-MS and/or HRMS, FTIR, HSQC, HMBC, H-1, C-13, and P-31 NMR spectroscopy and X-ray crystallography (for 4). It is observed that the 2,4-ansa and spiro-cyclotetraphosphazenes have different thermal stabilities. Additionally, the CVs of the new mono-ferrocenyl pendant-armed cyclotetraphosphazenes revealed electrochemically reversible one-electron oxidation of the Fe-redox centre. The 2,4-ansa phosphazenes (3 and 3a-3d) have two different stereogenic P centers indicating that they are expected to be in racemic mixtures (RR'/SS'). The chiralities of 3a and 3c were investigated by chiral HPLC. The manuscript also deals with the antimicrobial activities against G(+)/G(-) bacteria and fungi, the interactions with plasmid DNA, the in vitro cytotoxic activities against L929 fibroblast and MCF7 breast cells, and the antituberculosis activities against Mycobacterium tuberculosis H37Rv of the cyclotetraphosphazenes.en_US
dc.description.sponsorshipScientific and Technical Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [215Z496]; Hacettepe University Scientific Research Project UnitHacettepe University [013 D04 602 004]; Turkish Academy of Sciences (TUBA)Turkish Academy of Sciencesen_US
dc.description.sponsorshipThe authors thank the "Scientific and Technical Research Council of Turkey'' (Grant No. 215Z496). T.H. is grateful to Hacettepe University Scientific Research Project Unit (Grant No. 013 D04 602 004), and Z.K. thanks the Turkish Academy of Sciences (TUBA) for partial support of this work.en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1039/c9nj00577c
dc.identifier.endpage6873en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue18en_US
dc.identifier.scopus2-s2.0-85065540278
dc.identifier.scopusqualityQ2
dc.identifier.startpage6856en_US
dc.identifier.urihttps://doi.org/10.1039/c9nj00577c
dc.identifier.urihttps://hdl.handle.net/20.500.12587/7784
dc.identifier.volume43en_US
dc.identifier.wosWOS:000468633200006
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherRoyal Soc Chemistryen_US
dc.relation.ispartofNew Journal Of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.titlePhosphorus-nitrogen compounds. Part 42. The comparative syntheses of 2-cis-4-ansa(N/O) and spiro(N/O) cyclotetraphosphazene derivatives: spectroscopic and crystallographic characterization, antituberculosis and cytotoxic activity studiesen_US
dc.typeArticle

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