Phosphorus–nitrogen compounds: Part 28. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing vanillinato and pendant ferrocenyl groups

Tümer, Yasemin; Asmafiliz, Nuran; Kılıç, Zeynel; Hökelek, Tuncer; Koç, L. Yasemin; Açık, Leyla; Yola, Mehmet Lütfi; Solak, Alı Osman; Öner, Yağmur; Dündar, Devrim; Yavuz, Makbule

doi:10.1016/j.molstruc.2013.06.036

Cited by 51 publications

(27 citation statements)

References 37 publications

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“…The yields of all the non-geminal phosphazenes were higher than those of the geminal derivatives. In the earlier paper [14], the yields of geminal products, N 3 P 3 [FcCH 2 N(CH 2 ) n NR 1 ](C 8 H 7 O 3 ) 2 Cl 2 (R 1 = H, n = 3, 4), were found to be higher than non-geminal ones. The isolation of geminal and non-geminal (cis and/or trans) products are considerably noteworthy in the present work, since the Cl replacement reactions of bulkycrypta and pendant-ferrocenyl spiro cyclotriphosphazenes with the secondary amines (pyrrolidine, morpholine, DASD and 1-aza-12-crown-4-substituted) gave only the geminal compounds [21,27,32,34].…”

Section: Synthesis and Characterizationmentioning

confidence: 87%

“…On the other hand, it was found that the aryloxides react with Cl atoms to yield partly and fully substituted phosphazenes regio-and stereoselectively via generally the non-geminal pathway [12,13]. But, our group observed that tetrachloro mono and bisferrocenylphosphazenes with potassium vanillinate gave both of the geminal and nongeminal products [14].…”

Section: Introductionmentioning

confidence: 93%

“…The reported investigations are related with the stereogenic properties of cyclotriphosphazene derivatives, including the one, two equivalent and two different stereogenic centers. The chirality in cyclotriphosphazenes was identified by different methods, e.g., X-ray crystallography, CSA added NMR spectroscopy and/or chiral HPLC in the literature [10,14,16,36].…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Phosphorus–nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes

et al. 2014

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The gradual Cl replacement reactions of NN (1-3) or NO spirocyclic monoferrocenyl cyclotriphosphazenes (4 and 5) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) resulted in the mono (1a-5a), geminal (gem-1b-5b), non-geminal (cis-5b and trans -1b-4b), tri (1c, 3c-5c) and tetra-vanillinato-substituted phosphazenes (1d-5d). All the phosphazene derivatives have stereogenic P-center(s), except tetra-substituted ones. The vanillinatophosphazenes have reversible voltammograms with one-electron anodic and cathodic peaks which are attributed to ferrocenyl redox probe. The structures of the new phosphazene compounds were determined by FTIR, MS, (1)H, (13)C{(1)H} and (31)P{(1)H} NMR spectral data. The solid-state structure of cis -5b was examined by single-crystal X-ray diffraction techniques. In addition, the compounds were tested in HeLa cancer cell lines using MTT assay. The 12 phosphazene derivatives were screened for antimicrobial activity, and 3c was very effective against S. aureus even at 4.88 µM concentration, taking into account the MIC values. Besides, interactions between the phosphazenes and pBR322 plasmid DNA were also investigated.

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Section: Synthesis and Characterizationmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 93%

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Phosphorus–nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes

et al. 2014

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“…The coupling and 1141-1198 cm −1 , attributed to the ν P =N bonds of the trimeric phosphazene skeletons. 21 The asymmetric and symmetric vibrations of ν P Cl2 emerge for 2, dispiro 3b, and dispiro 3c of 580-575 and 545-531 cm −1 .…”

Section: Chemistrymentioning

confidence: 97%

The reactions of N$_{3}$P$_{3}$Cl$_{6}$ with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes

Okumuş¹,

Elmas²,

Kılıç³

et al. 2017

Turk J Chem

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Abstract:The Cl replacement reactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazene (2) with excess monoamines led to the formation of 4-fluorobenzylspiro(N/O)tetraaminocyclotriphosphazenes (2a-2d). The partly substituted dispiro 3b and dispiro 3c and fully substituted trispirocyclotriphosphazenes (trans 4a, cis 4c, 4d, and 4e) were obtained, respectively, from the reactions of 2 with one equimolar and two equimolar amounts of diamines, aminoalcohol, and diols. Although efforts were made for the separation of the cis/trans and optical isomers of the dispiro phosphazenes, only one set of diastereomers (RR/RS or SS/SR) of dispiro 3b and dispiro 3c was isolated, respectively. The 31 P NMR spectral data of the other dispiro phosphazenes were evaluated from the 31 P NMR spectra of the reaction mixtures. The reactions of 2 with excess N-methylethylenediamine gave trans 4a as a racemic mixture. While trans 4b(racemic) and cis 4b (meso) occurred from the reaction of 2 with excess N-methyl-1,3-propanediamine, they were not isolated separately. Some of the phosphazenes were screened against bacteria and fungi. The activities of the compounds against anaerobic and microaerophilic gram-negative bacteria were evaluated. It was found that compounds 2, 2b, and trans 4a exhibited tolerable toxic effects on fibroblast cells and had the highest toxicity against MCF-7 cells.

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“…In previous studies carried by our group, DNA interactions as well as cytotoxic and antimicrobial activities of ferrocenylphosphazene derivatives were investigated [12,13,14]. This study suggests that ferrocenylphosphazenes bearing a paraben derivative (ethyl-4-hydroxybenzoate) could show antimicrobial and cytotoxic activities, and DNA damaging properties.…”

Section: Introductionmentioning

confidence: 97%

Syntheses and Structural Characterization of Fırst Paraben Substituted Ferrocenyl Phosphazene Compounds

Tümer¹,

Şehirli²,

Ataol³

2016

Journal of the Turkish Chemical Society, Section A: Chemistry

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Phosphorus–nitrogen compounds: Part 28. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing vanillinato and pendant ferrocenyl groups

Cited by 51 publications

References 37 publications

Phosphorus–nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes

Phosphorus–nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes

The reactions of N$_{3}$P$_{3}$Cl$_{6}$ with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes

Syntheses and Structural Characterization of Fırst Paraben Substituted Ferrocenyl Phosphazene Compounds

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