Phosphorus-nitrogen compounds. Part 64. Comparative reactions of spiro and ansa (N/O) cyclotetraphosphazenes with bulky (4-fluorobenzyl) N/N and N/O donor type bidentate reagents: structure, stereogenic properties and cytotoxic activity studies

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dc.authoridOzgur (nee Yakut), Mehtap/0000-0002-6237-8522
dc.authoridELMAS, Gamze/0000-0003-4877-3697
dc.authoridCerci, Nebahat Aytuna/0000-0002-7864-7213
dc.contributor.authorElmas, Gamze
dc.contributor.authorBinici, Arzu
dc.contributor.authorYakut, Mehtap
dc.contributor.authorOkumus, Aytug
dc.contributor.authorKilic, Zeynel
dc.contributor.authorCosut, Bunyemin
dc.contributor.authorHokelek, Tuncer
dc.date.accessioned2025-01-21T16:43:26Z
dc.date.available2025-01-21T16:43:26Z
dc.date.issued2022
dc.departmentKırıkkale Üniversitesi
dc.description.abstractThe reaction of octachlorocyclotetraphosphazene, N4P4Cl8 (1) (OCCP, tetramer), with an equimolar amount of sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (L1) resulted in the formation of ferrocenyl-spiro-(2) and ferrocenyl-2-cis-4-dichloro-ansa-(3) cyclotetraphosphazenes. Both of the starting compounds were used to produce the new inorganic-organic hybrid multiheterocyclic-spiro and ansa cyclotetraphosphazenes. Spiro (2) was treated with excess N-(4-fluorobenzyl)-N'-ethyl-1,2-diaminoethane (L2) to give 2-trans-6-dispiro (trans-2a) and 2-trans-4-cis-6-trans-8-tetraspiro (tetraspiro-2a) cyclotetraphosphazenes. Spiro (2) was also reacted with excess sodium 3-(4-fluorobenzylamino)-1-propanoxide (L3) to produce 2-trans-6-dispiro (trans-2b), 2-cis-6-dispiro (cis-2b), 2-cis-4-trans-6-trispiro (trans-2c), 2-cis-4-dispiro-6-trispiro (cis-2c), 2-cis-4-dichloro-ansa-4-trans-6-spiro(N/O) (ansa-2b) and 2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (ansa-2c). The reactions of 2,4-ansa (3) with excess L2 led to the formation of 2-cis-4-dichloro-ansa-2-trans-6-spiro(N/N) (trans-3a) and 2-cis-4-dichloro-ansa-2-cis-6-spiro(N/N) (cis-3a) cyclotetraphosphazenes. However, the reactions of 2,4-ansa (3) with excess L3 afforded monospiro {2-cis-4-dichloro-ansa-4-trans-6-spiro(N/O) (trans-3b) and 2-cis-4-dichloro-ansa-4-cis-6-spiro(N/O) (cis-3b)} and dispiro {2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (trans-3c) and 2-cis-4-dichEoro-ansa-6-cis-8-dispiro(N/O) (cis-3c)}. The obtained products were characterized by spectroscopic techniques. The crystal structures of trans-2b and cis-3b were clarified by single crystal X-ray analysis. The products had stereogenic P-centres except for trans-2a, tetraspiro-2a, trans-2b and cis-2b. The stereogenic properties of tetrameric phosphazenes were evaluated by X-ray crystallography and chiral high performance liquid chromatography (HPLC) methods. The structure of cis-3b revealed the absolute configurations of the enantiomers (SS'R ''/RR'S ''). The broad HPLC peak of cis-3b indicates that it may exist as a resamate in solution. The cytotoxic activities of the cyclotetraphosphazenes were evaluated using an MTT assay against L929 mouse fibroblasts, A549 non-small lung cancer and Caco-2 colorectal adenocarcinoma cells. Compound cis-3b was found to be very effective in all cell lines up to 104.1 mu M.
dc.description.sponsorshipScientific and Technical Research Council of Turkey [215Z496]; Turkish Academy of Sciences (TuBA); Hacettepe University Scientific Research Unit [013 D04 602 004]
dc.description.sponsorshipThe authors thank the Scientific and Technical Research Council of Turkey (Grant no. 215Z496) and Z. K. thanks the Turkish Academy of Sciences (TuBA) for partial support of this work. T. H. is grateful to Hacettepe University Scientific Research Unit (Grant No. 013 D04 602 004).
dc.identifier.doi10.1039/d2nj02280j
dc.identifier.endpage16113
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue33
dc.identifier.scopus2-s2.0-85135536205
dc.identifier.scopusqualityQ2
dc.identifier.startpage16096
dc.identifier.urihttps://doi.org/10.1039/d2nj02280j
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25268
dc.identifier.volume46
dc.identifier.wosWOS:000837408100001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherRoyal Soc Chemistry
dc.relation.ispartofNew Journal of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.titlePhosphorus-nitrogen compounds. Part 64. Comparative reactions of spiro and ansa (N/O) cyclotetraphosphazenes with bulky (4-fluorobenzyl) N/N and N/O donor type bidentate reagents: structure, stereogenic properties and cytotoxic activity studies
dc.typeArticle

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