The comparative reactions of 2-cis-4-ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies

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dc.contributor.authorOkumuş, Aytuğ
dc.contributor.authorElmas, Gamze
dc.contributor.authorKılıç, Zeynel
dc.contributor.authorBinici, Arzu
dc.contributor.authorRamazanoğlu, Nagehan
dc.contributor.authorAçık, Leyla
dc.contributor.authorÇoşut, Bünyemin
dc.contributor.authorGüzel, Remziye
dc.contributor.orcid0000-0002-2169-5695
dc.contributor.orcid0000-0003-4877-3697
dc.contributor.orcid0000-0003-1061-8122
dc.contributor.orcid0000-0001-7470-4156
dc.contributor.orcid0000-0003-0541-9129
dc.contributor.orcid0000-0002-3672-8429
dc.contributor.orcid0000-0001-6530-0205
dc.contributor.orcid0000-0002-5781-6049
dc.date.accessioned2024-04-24T15:59:19Z
dc.date.available2024-04-24T15:59:19Z
dc.date.issued2021
dc.departmentDicle Üniversitesi, Ziya Gökalp Eğitim Fakültesi, Matematik ve Fen Bilimleri Eğitimi Bölümüen_US
dc.description.abstractIn this study, two kinds of compounds, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa- (2,4-ansa; 3) and mono-ferrocenyl-spiro- (spiro; 4) hexachlorocyclotetraphosphazenes, were obtained by the Cl replacement reaction of N4P4Cl8 (1) with an equimolar amount of sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (2). The reactions of 2,4-ansa (3) with excess diamines and dialkoxides resulted in the formation of ansa-cyclotetraphosphazenes (3a-3e). Spiro (4) was reacted with excess diamines and dialkoxides to give the mono-ferrocenyl-spiro-cyclotetraphosphazenes (4a-4d). Although 2,4-ansa (3) produced the dispiro (3a) with N-(4-fluorobenzyl)-N '-methylethane-1,2-diamine, it afforded both monospiro (3b) and dispiro (3c) with N-(4-fluorobenzyl)-N '-methylpropane-1,3-diamine. However, spiro (4) yielded a trispiro (4a) with N-(4-fluorobenzyl)-N '-methylethane-1,2-diamine and 2,6-dispiro (4b) with N-(4-fluorobenzyl)-N '-methylpropane-1,3-diamine. The structures of the phosphazenes were elucidated by FTIR, ESI-MS and/or HRMS, spectroscopic and crystallographic (for 3f and 4b) data. Furthermore, the electrochemical findings of cyclotetraphosphazenes exhibited electrochemically reversible one-electron oxidation of Fe-redox centre. As an example, the chirality of 3c was investigated by P-31 NMR spectroscopy on the addition of (R)-(+)-2,2,2-trifluoro-1-(9 '-anthryl)-ethanol, chiral solvating agent (CSA). The circular dichroism (CD) (for 3d and 3e), HPLC (for 3d, 3e and 3f) and X-ray (for 3f) display that these compounds have chirality (RS ' or SR ') in the solution and solid state. This paper also focuses on the antimicrobial activities, the interactions with pBR322 DNA, in vitro anticancer activity against L929 fibroblast and MCF7 breast cells, and antituberculosis activity against Mycobacterium tuberculosis H37Rv of the cyclotetraphosphazenes.en_US
dc.description.sponsorshipTurkish Academy of Sciences (TUBA); Hacettepe University Scientific Research Project Unit [013 D04 602 004]; Scientific and Technical Research Council of Turkey [215Z496]en_US
dc.description.sponsorshipTurkish Academy of Sciences (TUBA); Hacettepe University Scientific Research Project Unit, Grant/Award Number: 013 D04 602 004; Scientific and Technical Research Council of Turkey, Grant/Award Number: 215Z496en_US
dc.identifier.citationOkumuş, A., Elmas, G., Kılıç, Z., Binici, A., Ramazanoğlu, N., Açık, L. ve diğerleri. (2021). The comparative reactions of 2-cis-4-ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies. Applied Organometallic Chemistry, 35(4), 1-28.
dc.identifier.doi10.1002/aoc.6150
dc.identifier.endpage28
dc.identifier.issn0268-2605
dc.identifier.issn1099-0739
dc.identifier.issue4en_US
dc.identifier.scopus2-s2.0-85099086096
dc.identifier.scopusqualityQ1
dc.identifier.startpage1
dc.identifier.urihttps://doi.org/10.1002/aoc.6150
dc.identifier.urihttps://hdl.handle.net/11468/13975
dc.identifier.urihttps://onlinelibrary.wiley.com/doi/epdf/10.1002/aoc.6150
dc.identifier.volume35en_US
dc.identifier.wosWOS:000606489200001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorGüzel, Remziye
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofApplied Organometallic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAntituberculosis activityen_US
dc.subjectCyclotetraphosphazenesen_US
dc.subjectCytotoxic activityen_US
dc.subjectElectrochemistryen_US
dc.subjectSynthesisen_US
dc.titleThe comparative reactions of 2-cis-4-ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studiesen_US
dc.titleThe comparative reactions of 2-cis-4-ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies
dc.typeArticleen_US

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