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.authoridHokelek, Tuncer/0000-0002-8602-4382
dc.authoridELMAS, Gamze/0000-0003-4877-3697
dc.authoridRamazanoglu Bahadir, Nagehan/0000-0003-0541-9129
dc.authoridCosut, Bunyemin/0000-0001-6530-0205
dc.authoridAcik, Leyla/0000-0002-3672-8429
dc.contributor.authorOkumus, Aytug
dc.contributor.authorElmas, Gamze
dc.contributor.authorKilic, Zeynel
dc.contributor.authorBinici, Arzu
dc.contributor.authorRamazanoglu, Nagehan
dc.contributor.authorAcik, Leyla
dc.contributor.authorcosut, Bunyemin
dc.date.accessioned2025-01-21T16:44:54Z
dc.date.available2025-01-21T16:44:54Z
dc.date.issued2021
dc.departmentKırıkkale Üniversitesi
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.
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]
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: 215Z496
dc.identifier.doi10.1002/aoc.6150
dc.identifier.issn0268-2605
dc.identifier.issn1099-0739
dc.identifier.issue4
dc.identifier.scopus2-s2.0-85099086096
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1002/aoc.6150
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25547
dc.identifier.volume35
dc.identifier.wosWOS:000606489200001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley
dc.relation.ispartofApplied Organometallic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectantituberculosis activity; cyclotetraphosphazenes; cytotoxic activity; electrochemistry; synthesis
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.typeArticle

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