Phosphorus-nitrogen compounds: part 68. Synthesis, characterization, stereogenism, photophysical and bioactivity studies of novel unsymmetrical dispiro(N/N)cyclotriphosphazenes with carbazolyl and 4-chlorobenzyl pendant arms

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dc.authoridCosut, Bunyemin/0000-0001-6530-0205
dc.authoridHokelek, Tuncer/0000-0002-8602-4382
dc.authoridAcik, Leyla/0000-0002-3672-8429
dc.authorid, RESIT/0000-0002-2802-0754
dc.authoridCerci, Nebahat Aytuna/0000-0002-7864-7213
dc.contributor.authorCemaloglu, Resit
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorKilic, Zeynel
dc.contributor.authorCosut, Bunyemin
dc.contributor.authorSabah, Busra Nur
dc.contributor.authorAcik, Leyla
dc.contributor.authorCerci, Nebahat Aytuna
dc.date.accessioned2025-01-21T16:43:27Z
dc.date.available2025-01-21T16:43:27Z
dc.date.issued2023
dc.departmentKırıkkale Üniversitesi
dc.description.abstractOrganic-inorganic hybrid multi-heterocyclic unsymmetrical cis/trans dispirocyclotriphosphazenes with different pendant arms were obtained and their spectral, stereogenic, photophysical and bioactivity properties were investigated. To prepare these phosphazenes, the starting compounds tetrachloro(4-chlorobenzyl)spiro(N/N)cyclotriphosphazenes, (ClBzSpiro-5)R-1(N3P3)Cl-4 [Bz: Benzyl; R-1: Me (1) and R-1: Et (2)], were prepared regioselectively from the reactions of hexachlorocyclotriphosphazene, N3P3Cl6 (HCCP, trimer) with N-methyl/ethyl-N'-(4-chlorobenzyl)-1,2-diaminoethanes. Reactions of tetrachlorocyclotriphosphazenes (1 and 2) and 9-ethyl-N-methyl-3-carbazolyl-1,2-diaminoethane (3) or 9-ethyl-N-methyl-3-carbazolyl-1,3-diaminopropane (4) produce new cis/trans-dispirocyclotriphosphazenes, [(ClBzSpiro-5)R-1(N3P3)(CzSpiro-n)R-2]Cl-2 (Cz: Carbazolyl; R-1, R-2: Me or Et; n = 5 or 6; (5a-8a and 5b-8b), containing unsymmetrical spiro-architectures. In addition, the structures of trans-7a and cis-7b isomers were clarified by single crystal X-ray crystallography. The chiralities of trans-7a and cis-7b were confirmed using X-ray crystal structures, P-31 NMR spectra recorded upon the addition of chiral solvating agent [(S)-(+)-2,2,2-trifluoro-1-(9 & PRIME;-anthryl)ethanol; CSA], and circular dichroism (CD) spectra. Moreover, the photophysical properties of phosphazenes showed a fluorescence profile with lifetimes of about 4.9-6.6 ns and quantum yields in the range of 0.10-0.14. Additionally, the antibacterial and antifungal activities of the newly synthesized phosphazenes against some bacteria and yeast strains and their interactions with pBR322 plasmid DNA were investigated. The bacterial strain most susceptible (MIC = 156.3 mu M) to compounds 5a and 8a was P. aeruginosa. However, it was found that the yeast strain most susceptible (MIC = 156.3 mu M) to compounds 5b, 7a, 7b and 8b was C.albicans. The cytotoxic activities of 5a, 5b, 7b and 8a against L929 fibroblast and MCF-7 breast cancer cells were determined. However, cis-5b showed reasonable antioxidant activity with a radical scavenging value of 35.20%.
dc.description.sponsorshipTurkish Academy of Sciences (TUBA); Hacettepe University Scientific Research Project Unit [013 D04 602 004]
dc.description.sponsorshipZ. K. is thankful to the Turkish Academy of Sciences (TUEBA) for partial support of this work. T. H. is grateful to the Hacettepe University Scientific Research Project Unit (Grant No. 013 D04 602 004).
dc.identifier.doi10.1039/d2nj05010b
dc.identifier.endpage1915
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue4
dc.identifier.scopus2-s2.0-85145684131
dc.identifier.scopusqualityQ2
dc.identifier.startpage1900
dc.identifier.urihttps://doi.org/10.1039/d2nj05010b
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25271
dc.identifier.volume47
dc.identifier.wosWOS:000906747200001
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 68. Synthesis, characterization, stereogenism, photophysical and bioactivity studies of novel unsymmetrical dispiro(N/N)cyclotriphosphazenes with carbazolyl and 4-chlorobenzyl pendant arms
dc.typeArticle

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