Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm

Asmafiliz, Nuran; Berberoğlu, İpek; Özgür, Mehtap; Kılıç, Zeynel; Kayalak, Hande; Açık, Leyla; Türk, Mustafa; Hökelek, Tuncer

doi:10.1016/j.ica.2019.05.048

Cited by 27 publications

(27 citation statements)

References 49 publications

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“…Moreover, the average 2 J P P constants were 48.4 and 46.2 Hz for the products, including the 5-and 6-membered spiro rings. These findings were inconsistent with the literature data [28,29]. The shifts, multiplicities, and coupling constants of the phosphazenes in the 13 C and 1 H spectra were evaluated (Tables S1 and S2).…”

Section: Nmr and Ir Spectroscopiescontrasting

confidence: 78%

“…The carbon peaks of the phenyl rings, C1-C4, were assigned between 125.27 and 138.97 ppm (Table S1). The peaks of observed previously [28,29]. The same phosphorus atoms, to which 2 heterocyclic groups had bonded, showed 2…”

Section: Nmr and Ir Spectroscopiesmentioning

confidence: 56%

“…Replacement reactions of N 3 P 3 Cl 6 with the monodentate and bidentate amines. [28,29]. Although the trans-geometric isomers of these compounds were purely obtained, the cis-geometric isomers were not isolated from the reaction mixture using crystallization, column chromatography, or preparative TLC.…”

Section: Synthesismentioning

confidence: 99%

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Synthesis and spectroscopic properties of (N/O) mono- and dispirocyclotriphosphazene derivatives with benzyl pendant arms: study of biological activity

İşcan¹,

Cemaloğlu²,

Asmafiliz³

et al. 2020

Turk J Chem

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The Cl replacement reactions of hexachlorocyclotriphosphazene (trimer; N 3 P 3 Cl 6) with sodium (N-benzyl)aminopropanoxides (1 and 2) produced monospiro-(3 and 4), cis-, and trans-dispirocyclotriphosphazenes (13-16). The monospiro tetrakis-aminocyclotriphosphazenes (5-12) were obtained by the Cl substitutions of 3 and 4 with different secondary amines. The cis-(13 and 14) and trans-dispirophosphazenes (15 and 16) possessed 2 chiral P centers, and they were able to present meso and racemic forms, respectively. Moreover, the structures of compounds 5 and 14 were designated using X-ray data. The absolute configuration of compound 14 was found as SR in the solid state. Analytical and spectroscopic data of the phosphazenes were consistent with their suggested structures. Antimicrobial activities of the benzyl-pendant-armed cyclotriphosphazenes were scrutinized against G(+) and G(−) bacteria and yeast strains. The bacterium most affected by the synthesized compounds was Pseudomonas aeruginosa. Minimum inhibitory concentrations and minimal bacterial concentrations were in the range of 125-500 µ M. Interactions between the phosphazenes (3-12 and 15) and plasmid DNA were studied with agarose gel electrophoresis. The phosphazene-DNA interaction studies of the cyclotriphosphazenes revealed that phosphazenes 3, 4, and 15 had a substantial effect on supercoiled DNA by cleavage of the double helix.

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Section: Nmr and Ir Spectroscopiescontrasting

confidence: 78%

Section: Nmr and Ir Spectroscopiesmentioning

confidence: 56%

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Synthesis and spectroscopic properties of (N/O) mono- and dispirocyclotriphosphazene derivatives with benzyl pendant arms: study of biological activity

İşcan¹,

Cemaloğlu²,

Asmafiliz³

et al. 2020

Turk J Chem

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“…The CD spectra of some spiro‐ and bino‐phosphazenes with two equivalent chiral P‐centres were also reported in the literature. [ 11,42 ]…”

Section: Resultsmentioning

confidence: 99%

“…[ 10 ] Also, the combination of circular dichroism (CD) and X‐ray crystallography techniques was very useful for determining the absolute configurations of trimeric phosphazenes as reported in the literature. [ 11 ] However, although there are some papers investigating the chiralities of cyclotetraphosphazenes using X‐ray crystallography, 31 P‐NMR spectroscopy and HPLC techniques, [ 12 ] no reports using the CD technique was published until now. But, in the present paper, the enantiomers of two tetrameric phosphazenes were distinguished by CD and HPLC data.…”

Section: Introductionmentioning

confidence: 99%

The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies

Okumuş

Elmas

Kılıç

et al. 2021

Applied Organom Chemis

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In this study, two kinds of compounds, namely, mono‐ferrocenyl‐2‐cis‐4‐dichloro‐ansa‐ (2,4‐ansa; 3) and mono‐ferrocenyl‐spiro‐ (spiro; 4) hexachlorocyclotetraphosphazenes, were obtained by the Cl replacement reaction of N4P4Cl8 (1) with an equimolar amount of sodium 3‐(N‐ferrocenylmethylamino)‐1‐propanoxide (2). The reactions of 2,4‐ansa (3) with excess diamines and dialkoxides resulted in the formation of ansa‐cyclotetraphosphazenes (3a–3e). Spiro (4) was reacted with excess diamines and dialkoxides to give the mono‐ferrocenyl‐spiro‐cyclotetraphosphazenes (4a–4d). Although 2,4‐ansa (3) produced the dispiro (3a) with N‐(4‐fluorobenzyl)‐N′‐methylethane‐1,2‐diamine, it afforded both monospiro (3b) and dispiro (3c) with N‐(4‐fluorobenzyl)‐N′‐methylpropane‐1,3‐diamine. However, spiro (4) yielded a trispiro (4a) with N‐(4‐fluorobenzyl)‐N′‐methylethane‐1,2‐diamine and 2,6‐dispiro (4b) with N‐(4‐fluorobenzyl)‐N′‐methylpropane‐1,3‐diamine. The structures of the phosphazenes were elucidated by FTIR, ESI‐MS and/or HRMS, spectroscopic and crystallographic (for 3f and 4b) data. Furthermore, the electrochemical findings of cyclotetraphosphazenes exhibited electrochemically reversible one‐electron oxidation of Fe‐redox centre. As an example, the chirality of 3c was investigated by 31P NMR spectroscopy on the addition of (R)‐(+)‐2,2,2‐trifluoro‐1‐(9′‐anthryl)‐ethanol, chiral solvating agent (CSA). The circular dichroism (CD) (for 3d and 3e), HPLC (for 3d, 3e and 3f) and X‐ray (for 3f) display that these compounds have chirality (RS′ or SR′) in the solution and solid state. This paper also focuses on the antimicrobial activities, the interactions with pBR322 DNA, in vitro anticancer activity against L929 fibroblast and MCF7 breast cells, and antituberculosis activity against Mycobacterium tuberculosis H37Rv of the cyclotetraphosphazenes.

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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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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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Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm

Cited by 27 publications

References 49 publications

Synthesis and spectroscopic properties of (N/O) mono- and dispirocyclotriphosphazene derivatives with benzyl pendant arms: study of biological activity

Synthesis and spectroscopic properties of (N/O) mono- and dispirocyclotriphosphazene derivatives with benzyl pendant arms: study of biological activity

The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies

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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