Phosphorus-nitrogen compounds. Part 37. Syntheses and structural characterizations, biological activities of mono and bis(4-fluorobenzyl)spirocyclotetraphosphazenes

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dc.contributor.authorElmas, Gamze
dc.contributor.authorOkumus, Aytug
dc.contributor.authorSevinc, Pelin
dc.contributor.authorKilic, Zeynel
dc.contributor.authorAcik, Leyla
dc.contributor.authorAtalan, Mustafa
dc.contributor.authorHokelek, Tuncer
dc.date.accessioned2020-06-25T18:22:52Z
dc.date.available2020-06-25T18:22:52Z
dc.date.issued2017
dc.departmentKırıkkale Üniversitesi
dc.descriptionHokelek, Tuncer/0000-0002-8602-4382; okumus, aytug/0000-0002-2169-5695
dc.description.abstractThe Cl substitution reactions of octachlorocyclotetraphosphazene, N4P4Cl8, with one equimolar amount of (4-fluorobenzyl)diamines (1-3) affords mono(4-fluorobenzyl) spirocyclotetraphosphazenes (4-6) as minor products. However, the reactions of N4P4Cl8 with two equimolar amounts of (4-fluorobenzyl) diamines (1-3) leads to the formation of mono (4-6), 2-trans-6-bis (7-9, as major products) and 2-cis-6-bis (4-fluorobenzyl) spirocyclotetraphosphazenes (10-12). The 2-cis-6-bis compounds (10 and 12) were separated and purified using column chromatography as minor products, whereas compound 11 could not be isolated. The mono-spiro (4-6) and 2-trans-6-bis-spiro (7-9) cyclotetraphosphazenes were reacted with excess pyrrolidine in THF to afford the fully substituted hexapyrrolidino (4a-6a) and tetra-pyrrolidino (7a-9a) products in high yield. Compound 9 was also reacted with piperidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD) to obtain the tetraamino products (9b, 9c and 9d), respectively, due to its very high yield. The elemental analyses, mass spectra (ESI-MS), Fourier transform infrared (FTIR) spectra, and H-1, C-13{H-1}, and P-31{H-1} NMR data of the cyclotetraphosphazenes were in agreement with the suggested structures. The molecular structures of 7, 9 and 12 were established by X-ray crystallography. The antibacterial activities of the compounds against G(+) and G(-) bacteria and their antifungal activities against yeast strains were scrutinized. The results indicated that 4a and 5a were the most active compounds, especially to yeast strains. In addition, it was found that the most active compound toward DNA was 8. The cytotoxic activities of the cyclotetraphosphazenes against L929 fibroblast and MCF-7 breast cancer cell lines were elucidated. Compound 8a exhibited the most toxic effects against both types of cells.en_US
dc.description.sponsorshipTurkish Academy of Sciences (TUBA)Turkish Academy of Sciencesen_US
dc.description.sponsorshipThe author Z. K. thanks the Turkish Academy of Sciences (TUBA) for partial support of this study.en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1039/c7nj00478h
dc.identifier.endpage5835en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue13en_US
dc.identifier.scopus2-s2.0-85021703058
dc.identifier.scopusqualityQ2
dc.identifier.startpage5818en_US
dc.identifier.urihttps://doi.org/10.1039/c7nj00478h
dc.identifier.urihttps://hdl.handle.net/20.500.12587/6937
dc.identifier.volume41en_US
dc.identifier.wosWOS:000404350900068
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 37. Syntheses and structural characterizations, biological activities of mono and bis(4-fluorobenzyl)spirocyclotetraphosphazenesen_US
dc.typeArticle

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