Phosphorus–nitrogen compounds: Part 19. Syntheses, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic monoferrocenylcyclotriphosphazenes

İlter, Elif Ece; Asmafiliz, Nuran; Kılıç, Zeynel; Açık, Leyla; Yavuz, Makbule; Bali, Elif Burcu; Solak, Alı Osman; Büyükkaya, Fevziye; Dal, Hakan; Hökelek, Tuncer

doi:10.1016/j.poly.2010.07.017

Cited by 58 publications

(41 citation statements)

References 46 publications

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“…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]. In addition, if 1 equiv of 1-5 and 3 equiv of potassium vanillinate were used in the reactions, the tri-(1c-5c, as major products) and tetra-substituted phosphazenes (1d-5d) were prepared.…”

Section: Synthesis and Characterizationmentioning

confidence: 76%

“…The ferrocenylamines [26,27] and tetrachloro monoferrocenylphosphazenes (1, 2 and 5) [27] were obtained according to the modified methods reported in the literature. The syntheses, purifications, melting points, yields, elemental analyses, FTIR and APIES-MS data of the new phosphazene derivatives are given in the Supplementary Material.…”

Section: Methodsmentioning

confidence: 99%

“…The tetrachloro NN or NO spirocyclo monoferrocenyl cyclotriphosphazenes (1, 2 and 5, Scheme 1) were prepared according to the published procedure [27]. The new tetrachloro ferrocenylphosphazenes (3 and 4) were obtained from the reactions of N 3 P 3 Cl 6 with N-(1-ferrocenyl methyl)-N-methyl-propylenediamine and sodium [2-(N-ferrocenyl methyl amino)-1-ethanoxide, respectively.…”

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: 76%

Section: Methodsmentioning

confidence: 99%

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

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“…The starting compounds (1)(2)(3)(4)(5) were synthesized in accordance with the published procedure [14,15]. These precursor compounds have four reactive P-Cl bonds which may be replaced by the nucleophiles.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…This study suggests that ferrocenylphosphazenes bearing a paraben derivative (ethyl-4-hydroxybenzoate) could show antimicrobial and cytotoxic activities, and DNA damaging properties. For this purpose, the tetrachloro spirocyclotriphosphazenes with ferrocenyl substituents on the spirocyclic unit (1-5) were synthesized as precursor materials which have four active P-Cl bonds [14,15]. The substitution reactions of 1-5 with ethyl-4-hydroxybenzoate were carried out as emphasized.…”

Section: Introductionmentioning

confidence: 99%

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 39. Syntheses and Langmuir‐Blodgett thin films and antimicrobial activities of N/N and N/O spirocyclotriphosphazenes with monoferrocenyl pendant arm

Asmafiliz

Civan

Özben

et al. 2018

Applied Organom Chemis

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The Cl substitution reactions of the N/N (1-3) and N/O (4 and 5) spirocyclic monoferrocenylphosphazenes with 1,4-dioxa-8-azaspiro [4,5]decane (DASD) produce the mono-(1a-5a), geminal-(1b-5b) and tetrakis-DASD-substituted ferrocenylspirocyclotriphosphazenes (1c-5c). The mono-and geminal-DASDsubstituted phosphazenes have two and one stereogenic P-centers, respectively. The structures of the compounds were established by spectroscopic techniques.The molecular structures of 3a and 2b were evaluated using X-ray crystallography. Additionally, the ultrathin and highly ordered Langmuir-Blodgett (LB) films of 3a and 2b were also prepared. The characterizations of the LB films were done using p-polarized grazing angle (GAIR) and horizontal attenuated total reflectance (HATR) techniques. On the other hand, the antimicrobial activities of the eight phosphazene derivatives against G(+) and G(-) bacteria and fungi were investigated. Furthermore, the interactions between the compounds and plasmid DNA were studied by agarose gel electrophoresis. isomers may cause to the possibilities of optical isomers.On the other hand, phosphazene derivatives and polyorganophosphazenes are very useful compounds in technological and medicinal areas. They are used as flame retardant additives, [5] electrolytes for lithiumion batteries, [6,7] liquid crystals, [8,9] lubricants, [10] fluorescence chemosensor [11,12] and elastomers. [13] Recently, cyclotriphosphazene derivatives have also attracted a quite of interest for the preparation of the selective anticancer agents, [14] antibacterial and antifungal reagents, [15] and biomedical materials such as synthetic bones. [16] Furthermore, the potential anticancer activities of some of the mono and polyamino substituted cyclotriphosphazenes were reported. [17,18] Besides, the ultrathin films of the obtained inorganic or organic compounds have attracted much interest for applications as industrial materials, as well, such as detectors, sensors, and electronic circuit components. [19] The thin films were prepared using a solid substrate with different methods e.g. thermal evaporation, adsorption from solution, electrodeposition, sputtering, self-assembly molecular beam epitaxy, and Langmuir-Blodgett (LB) techniques. [20,21] There is only one report in the literature about the LB thin films of the phosphazene derivatives published by our group. [22] This study focused on the consecutive Cl replacement reactions of the tetrachloro monoferrocenylphosphazenes (1-5) with DASD for the aim of the obtaining of electronrich reservoir phosphazenes. Thereof, the mono-(1a-5a), geminal (1b-5b) and tetra-DASD-substituted (1c-5c) ferrocenylphosphazenes were synthesized by the reaction of 1-5 with DASD. In addition, the successive substitution reactions of Cl atoms from the pendant armed tetrachloroferrocenylphosphazenes (1-5) emerges a number of different possibilities in terms of regio-and stereoisomer selections. Eventually, we strongly stated that these compounds have been synthesized to investigate their biol...

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Phosphorus–nitrogen compounds: Part 19. Syntheses, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic monoferrocenylcyclotriphosphazenes

Cited by 58 publications

References 46 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

Syntheses and Structural Characterization of Fırst Paraben Substituted Ferrocenyl Phosphazene Compounds

Phosphorus‐nitrogen compounds. Part 39. Syntheses and Langmuir‐Blodgett thin films and antimicrobial activities of N/N and N/O spirocyclotriphosphazenes with monoferrocenyl pendant arm

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