The reactions of N3P3Cl6 with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes

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dc.contributor.authorOkumus, Aytug
dc.contributor.authorElmas, Gamze
dc.contributor.authorKilic, Zeynel
dc.contributor.authorRamazanoglu, Nagehan
dc.contributor.authorAcik, Leyla
dc.contributor.authorTurk, Mustafa
dc.contributor.authorAkca, Gulcin
dc.date.accessioned2025-01-21T16:55:12Z
dc.date.available2025-01-21T16:55:12Z
dc.date.issued2017
dc.departmentKırıkkale Üniversitesi
dc.description.abstractThe Cl replacement reactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazene (2) with excess monoamines led to the formation of 4-fluorobenzylspiro(N/O)tetraaminocyclotriphosphazenes (2a-2d). The partly substituted dispiro 3b and dispiro 3c and fully substituted trispirocyclotriphosphazenes (trans 4a, cis 4c, 4d, and 4e) were obtained, respectively, from the reactions of 2 with one equimolar and two equimolar amounts of diamines, aminoalcohol, and diols. Although efforts were made for the separation of the cis/trans and optical isomers of the dispiro phosphazenes, only one set of diastereomers (RR/RS or SS/SR) of dispiro 3b and dispiro 3c was isolated, respectively. The P-31 NMR spectral data of the other dispiro phosphazenes were evaluated from the P-31 NMR spectra of the reaction mixtures. The reactions of 2 with excess N-methylethylenediamine gave trans 4a as a racemic mixture. While trans 4b (racemic) and cis 4b (meso) occurred from the reaction of 2 with excess N-methyl-1,3-propanediamine, they were not isolated separately. Some of the phosphazenes were screened against bacteria and fungi. The activities of the compounds against anaerobic and microaerophilic gram-negative bacteria were evaluated. It was found that compounds 2, 2b, and trans 4a exhibited tolerable toxic effects on fibroblast cells and had the highest toxicity against MCF-7 cells.
dc.description.sponsorshipAnkara University Scientific Research Unit Grant [15H0430005]; Turkish Academy of Sciences (TUBA)
dc.description.sponsorshipThis study was supported by Ankara University Scientific Research Unit Grant No. 15H0430005. Author ZK thanks the Turkish Academy of Sciences (TUBA) for partial support of this work.
dc.identifier.doi10.3906/kim-1612-80
dc.identifier.endpage547
dc.identifier.issn1300-0527
dc.identifier.issue4
dc.identifier.scopusqualityQ3
dc.identifier.startpage525
dc.identifier.urihttps://doi.org/10.3906/kim-1612-80
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25724
dc.identifier.volume41
dc.identifier.wosWOS:000409378100006
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTubitak Scientific & Technological Research Council Turkey
dc.relation.ispartofTurkish Journal of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_20241229
dc.subjectMonofluorobenzyl(N/O)spirocyclotriphosphazenes; spectroscopy; antimicrobial activity; DNA interaction
dc.titleThe reactions of N3P3Cl6 with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes
dc.typeArticle

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