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

Gündüz, Ezel Öztürk; Okumuş, Aytuğ; Kılıç, Zeynel; Kılıç, Adem; Kayalak, Hande; Açık, Leyla; Çerçi, Nebahat Aytuna; Türk, Mustafa; Hökelek, Tuncer

doi:10.1016/j.ica.2018.10.028

Cited by 31 publications

(7 citation statements)

References 49 publications

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“…The average experimental exocyclic P-N bond lengths are found to be greater than the average endocyclic P-N bond lengths for the other aminocyclotriphosphazenes given in the literature. [20] On the other hand, as expected, the theoretical average exocyclic P-N bond lengths are greater than the theoretical average endocyclic P-N bond lengths, while the optimized bond lengths are longer than the experimentally obtained values. These results are not surprising because the calculated results are based on isolated molecules in the solid state, and the packaging effects are in motion with intermolecular interactions in the solid state.…”

Section: Syntheses and Characterizationssupporting

confidence: 55%

Phosphorus‐nitrogen compounds part 59. The syntheses of tetrachloro and tetraamino‐2‐pyridylmethylspiro(N/N)ethylenediaminocyclotriphosphazenes: Structural characterization, bioactivity, and molecular docking studies

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Elmas

Yakut

et al. 2021

J Chinese Chemical Soc

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In this study, primarily, tetrachloro-2-pyridylmethylspiro-N/N-ethylenediaminocyclotriphosphazenes (4 and 5) were prepared from the reactions of equimolar amounts of N-alkyl-N 0 -2-pyridylmethylethylenediamines, [PyCH 2 NH(CH 2 ) 2 NHR (R:CH 3 , 2 and R:C 2 H 5 , 3)], and hexachlorocyclotriphosphazene [(HCCP, trimer), N 3 P 3 Cl 6 (1)]. Compounds 4 and 5 react with secondary amines to yield the fully substituted tetraamino-2-pyridylmethylspiro-N/N-ethylenediaminocyclotriphosphazenes (4a-5c) in dry THF, respectively. These derivatives were obtained by both conventional and microwave-assisted reactions, and their yields were compared. In addition, it should also be noted that these cyclotriphosphazenes were obtained for use in the investigation of their spectral, crystallographic, antimicrobial, and anticancer properties. The structures of the compounds were elucidated by spectral data. The crystal structures of 4, 5a, and 5c were clarified by the single crystal X-ray diffraction technique. Antibacterial activities and biofilm preventions of 4a-c and 5a-c against bacteria, and their antifungal activities against fungi were investigated. According to broth microdilution method, the results showed that all compounds were highly effective against C. albicans. The interactions of these compounds with DNA and their cytotoxic activities against L929 fibroblast and A549 lung cancer cell lines were investigated. In addition, Density Functional Theory (DFT) calculations of 4, 5a, and 5c were made, and molecular docking studies with DNA and cytochrome P450 enzyme were presented.

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Section: Syntheses and Characterizationssupporting

confidence: 55%

Phosphorus‐nitrogen compounds part 59. The syntheses of tetrachloro and tetraamino‐2‐pyridylmethylspiro(N/N)ethylenediaminocyclotriphosphazenes: Structural characterization, bioactivity, and molecular docking studies

Bozkurt

Elmas

Yakut

et al. 2021

J Chinese Chemical Soc

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“…However, as previously observed in some phosphazene architectures, the enantiomers have been found to be crystallized spontaneously from the racemic mixtures in some bulky substituted chiral compounds. 4 a ,8 a ,9…”

Section: Resultsmentioning

confidence: 99%

“…8 Among these techniques, X-ray crystallography is the most reliable and powerful method as it clearly reveals the absolute configuration of chiral isomers. 9…”

Section: Introductionmentioning

confidence: 99%

Phosphorus–nitrogen compounds. Part 65. Novel diansa-spiro-cyclotetraphosphazenes: synthesis, characterization, bioactivity and electrochemical properties, and dye-sensitized solar cell fabrication studies

et al. 2022

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“…Phosphazenes are one of the most studied classes of inorganic heterocyclic molecules [1]. The significance of this class is due to their wide application areas, such as medicine, biology, flame-retardant additives, membranes, microlithography, and ionic crystals [2][3][4][5]. In these studies, cyclotriphosphazenes are widely used as a core platform to develop tailor-made systems, because cyclotriphosphazene can easily be tuned by nucleophilic substitution reactions [6].…”

Section: Introductionmentioning

confidence: 99%

Novel BODIPY-bridged cyclotriphosphazenes

2020

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Three new 2-component unsubstituted (4P), diiodo-(5P), and dibromo-(6P) distyryl-BODIPY-bridged cyclotriphosphazene dimers were designed and synthesized. The newly synthesized BODIPY-cyclotriphosphazene systems were characterized by 1 H, 13 C, and 31 P NMR spectroscopy. The photophysical properties of the distryl-BODIPYs (4-6) and BODIPY-cyclotriphosphazene dyads (4P-6P) were studied by UV-Vis absorption and fluorescence emission spectroscopy. In these derivatives, the bino-type cyclotriphosphazene derivative bearing unsubstituted BODIPY unit 4 P exhibited high fluorescence and no singlet oxygen generation due to the lack of spin converter. The attachment of heavy atoms (iodine and bromine) enabled the production of singlet oxygen. The bino-type BODIPY-cyclotriphosphazenes (5P and 6P) were also used as triplet photosensitizers in the photooxidation of 1,3-diphenylisobenzofuran to endoperoxide via generation of the singlet oxygen in dichloromethane. The singlet oxygen production of these compounds was also investigated via a direct method and produced a singlet oxygen phosphorescence peak at 1270 nm.

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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

Cited by 31 publications

References 49 publications

Phosphorus‐nitrogen compounds part 59. The syntheses of tetrachloro and tetraamino‐2‐pyridylmethylspiro(N/N)ethylenediaminocyclotriphosphazenes: Structural characterization, bioactivity, and molecular docking studies

Phosphorus‐nitrogen compounds part 59. The syntheses of tetrachloro and tetraamino‐2‐pyridylmethylspiro(N/N)ethylenediaminocyclotriphosphazenes: Structural characterization, bioactivity, and molecular docking studies

Phosphorus–nitrogen compounds. Part 65. Novel diansa-spiro-cyclotetraphosphazenes: synthesis, characterization, bioactivity and electrochemical properties, and dye-sensitized solar cell fabrication studies

Novel BODIPY-bridged cyclotriphosphazenes

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