Phosphorus-Nitrogen Compounds. 21. Syntheses, Structural Investigations, Biological Activities, and DNA Interactions of New N/O Spirocyclic Phosphazene Derivatives. The NMR Behaviors of Chiral Phosphazenes with Stereogenic Centers upon the Addition of Chiral Solvating Agents

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dc.contributor.authorIşıklan, Muhammet
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorÖzalp, Ezgi Elif
dc.contributor.authorİlter, Elif Ece
dc.contributor.authorKılıç, Zeynel
dc.contributor.authorÇoşut, Bünyemin
dc.contributor.authorAkyüz, Emel
dc.date.accessioned2020-06-25T17:49:20Z
dc.date.available2020-06-25T17:49:20Z
dc.date.issued2010
dc.departmentKırıkkale Üniversitesi
dc.descriptionHokelek, Tuncer/0000-0002-8602-4382; COSUT, Bunyemin/0000-0001-6530-0205;
dc.description.abstractThe reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N/O-donor-type N-alkyl (or aryl)-o-hydroxybenzylamines (la-le) produce mono- (2a-2e), di- (3a-3d), and tri- (4a and 4b) spirocyclic phosphazenes. The tetrapyrrolidino monospirocyclic phosphazenes (2f-2i) are prepared from the reactions of partly substituted compounds (2a-2d) with excess pyrrolidine. The dispirodipyrrolidinophosphazenes (3e-3h) and trispirophosphazenes (3i-3k) are obtained from the reactions of trans-dispirophosphazenes with excess pyrrolidine and sodium (3-amino-1-propanoxide), respectively. Compounds 3a-3d have cis and trans geometric isomers. Only the trans isomers of these compounds are isolated. Compounds 3a-3h have two stereogenic P atoms. They are expected to be in cis (meso) and trans (racemic) geometric isomers. In the trans trispiro compounds (3i-3k), there are three stereogenic P atoms. They are expected to be in racemic mixtures. The stereogenic properties of 3a-3k are confirmed by P-31 NMR spectroscopy upon the addition of the chiral solvating agent; (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol. The molecular structures of 3i-3k, 4a, and 4b look similar to a propeller, where the chemical environment of one P atom is different from that of others. Additionally, 4a and 4b are also expected to exist as cis-trans-trans and cis-cis-cis geometric isomers, but both of them are found to be in cis-trans-trans geometries. The solid-state structures of 2a, 2e, 2f, 3e, and 31 are determined by X-ray crystallography. The compounds 2f-2i, 3e-3i, and 3k are screened for antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against yeast strains. These compounds (except 3f) have shown a strong affinity against most of the bacteria. Minimum inhibitory concentrations (MIC) are determined for 2f-2i, 3e-3i, and 3k. DNA binding and the nature of interaction with pUC18 plasmid DNA are studied. The compounds 2f-2i, 3e-3i, and 3k induce changes on the DNA mobility. The prevention of BamHI and HindIII digestion (except 2g) with compounds indicates that the compounds bind with nucleotides in DNA.en_US
dc.description.sponsorshipScientific and Technical Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [106T503]; Hacettepe University, Scientific Researchs UnitHacettepe University [02 02 602 002]en_US
dc.description.sponsorshipThe authors acknowledge the Scientific and Technical Research Council of Turkey (Grant 106T503). T. H. is indebted to Hacettepe University, Scientific Researchs Unit (Grant 02 02 602 002) for financial support.en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1021/ic100781v
dc.identifier.endpage7071en_US
dc.identifier.issn0020-1669
dc.identifier.issn1520-510X
dc.identifier.issue15en_US
dc.identifier.pmid20583756
dc.identifier.scopus2-s2.0-77954961278
dc.identifier.scopusqualityQ1
dc.identifier.startpage7057en_US
dc.identifier.urihttps://doi.org/10.1021/ic100781v
dc.identifier.urihttps://hdl.handle.net/20.500.12587/4693
dc.identifier.volume49en_US
dc.identifier.wosWOS:000280365300046
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Socen_US
dc.relation.ispartofInorganic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.titlePhosphorus-Nitrogen Compounds. 21. Syntheses, Structural Investigations, Biological Activities, and DNA Interactions of New N/O Spirocyclic Phosphazene Derivatives. The NMR Behaviors of Chiral Phosphazenes with Stereogenic Centers upon the Addition of Chiral Solvating Agentsen_US
dc.typeArticle

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