Phosphorus-nitrogen compounds. Part 44. The syntheses of N,N-spiro bridged cyclotriphosphazene derivatives with (4-fluorobenzyl) pendant arms: Structural and stereogenic properties, DNA interactions, antimicrobial and cytotoxic activities

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dc.contributor.authorOzturk, Ezel
dc.contributor.authorOkumus, Aytug
dc.contributor.authorKilic, Zeynel
dc.contributor.authorKilic, Adem
dc.contributor.authorKayalak, Hande
dc.contributor.authorAcik, Leyla
dc.contributor.authorHokelek, Tuncer
dc.date.accessioned2020-06-25T18:34:18Z
dc.date.available2020-06-25T18:34:18Z
dc.date.issued2019
dc.departmentKırıkkale Üniversitesi
dc.descriptionokumus, aytug/0000-0002-2169-5695; Ozturk, Ezel/0000-0002-7770-8811
dc.description.abstractIsopropylaminopentachlorocyclotriphosphazene, (N3P3Cl5(NHCHMe2) (1), containing a P-NH group in the alkyl-chain, gives the NN-spirobridged octachlorobiscyclotriphosphazene, [N3P3Cl4(NCHMe2)](2) (2), in the presence of NaH. The reactions of 2 with excess pyrrolidine result in the formation of the fully substituted bridged product 2a. The reactions of 2 with 1:1 and 1:2 equimolar amounts of N-(4-fluorobenzyl)N'methylethane-1,2-diamine and N-(4-fluorobenzyl)-N'methylpropane-1,3-diamine produce the (4-fluorobenzyl) pendant armed monospiro (2b and 2c) and dispiro (2f and 2g) products. These compounds react with excess pyrrolidine to form stable, fully substituted cyclotriphosphazenes (2d, 2e, 2h and 2i). The structures of 2a and 2f are determined by X-ray crystallography. The stereogenic properties of 2a and 2f having four potential stereogenic P-centers are investigated by crystallography. The monospiro (2b-2e) and dispiro (2f-2i) products have one and two equivalent chiral centers, respectively. The dispiro derivatives may have two meso (trans-trans and cis-cis) and two racemate (trans-cis and cis-trans) mixtures. However, the structure of 2f is found to be as trans-trans (meso) isomer. Besides, in vitro antimicrobial and cytotoxic activities of 2d and 2h are evaluated. The compounds exhibit significant growth inhibitory effects on E. coli and B. cereus bacteria. Compound 2d has high anticancer and apoptotic activities.en_US
dc.description.sponsorshipTurkish Academy of Sciences (TUBA)Turkish Academy of Sciences; Hacettepe University, TurkeyHacettepe University [013D04602004]en_US
dc.description.sponsorshipThe author Z.K. thanks to Turkish Academy of Sciences (TUBA) for the partial support of this study, and T.H. acknowledges the financial support of this work by Hacettepe University, Turkey, Scientific research Unit (Grant No: 013D04602004).en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1016/j.ica.2018.10.028
dc.identifier.endpage184en_US
dc.identifier.issn0020-1693
dc.identifier.issn1873-3255
dc.identifier.scopus2-s2.0-85055730920
dc.identifier.scopusqualityQ2
dc.identifier.startpage172en_US
dc.identifier.urihttps://doi.org/10.1016/j.ica.2018.10.028
dc.identifier.urihttps://hdl.handle.net/20.500.12587/7861
dc.identifier.volume486en_US
dc.identifier.wosWOS:000454151300024
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier Science Saen_US
dc.relation.ispartofInorganica Chimica Acta
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectSpiro - bridged phosphazeneen_US
dc.subjectStereoisomeren_US
dc.subjectCrystallographyen_US
dc.subjectAntimicrobial activityen_US
dc.titlePhosphorus-nitrogen compounds. Part 44. The syntheses of N,N-spiro bridged cyclotriphosphazene derivatives with (4-fluorobenzyl) pendant arms: Structural and stereogenic properties, DNA interactions, antimicrobial and cytotoxic activitiesen_US
dc.typeArticle

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