Synthesis and spectroscopic characterizations of hexakis[(1-(4′-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-one)]cyclotriphosphazenes: their<i>in vitro</i>cytotoxic activity, theoretical analysis and molecular docking studies

Doğan, Hacer; Bahar, Mehmet Refik; Çalışkan, Eray; Tekin, Suat; Uslu, Harun; Akman, Feride; Koran, Kenan; Sandal, Süleyman; Görgülü, Ahmet Orhan

doi:10.1080/07391102.2020.1846621

Cited by 17 publications

(11 citation statements)

References 62 publications

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“…Yield: 0.47 g (37%), mp: 138. 13 C NMR (100 MHz, CDCl 3 , ppm): δ 160.14 (d, 3 J PC = 7.0 Hz, C 2 ), 148.77 (s, C 6 ), 136.41 (s, C 4 ), 121.95 (s, C 3 ), 121.72 (s, C 5 ), 51.17 (d, 2 J PC = 6.6 Hz, Py-CH 2 -N), 47.17…”

Section: Synthesis Of 4amentioning

confidence: 99%

“…(P=N). 1 H NMR (400 MHz, CDCl 3 , ppm): δ 8.46 (d, H, 3 J HH = 4.8, 4 J HH = 1.0 Hz, H 6 ), 7.76 (d, H, 3 J HH = 7.6 Hz, H 3 ), 7.62 (dd, H, 3 J HH = 7.6 Hz, 3 J HH = 8.0 Hz, H 4 ), 7.11 (dd, H, 3 J HH = 4.8 Hz, 3 J HH = 8.0 Hz, H 5 ), 4.18 (d, 2H, 3…”

Section: Synthesis Of 5amentioning

confidence: 99%

“…[2] In fact, the N 3 P 3 ring of HCCP has been extensively used as a scaffold for the organocyclotriphosphazenes, as it is a very robust ring. [3] As known, HCCP has six Cl atoms, which can be easily replaced with different functional reagents. For instance, when reactions between trimer and monodentate ligands are carried out stepwise, partially and fully substituted compounds are produced.…”

Section: Introductionmentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 , ppm): δ 8.53 (d, H,3 J HH = 7.4 Hz, HH = 2.0 Hz H 6 ), 7.62 (dd, H, 3 J HH = 7.2 Hz, HH = 8.0 Hz, 4 J HH = 2.0 Hz, H 4 ), 7.58 (d, H, HH = 8.0 Hz, H 3 ), 7.12 (dd, H,3 J HH = 7.2 Hz, HH = 7.4 Hz, 4 J HH = 1.2 Hz, H 5 ), 4.21 (d, 2H, PH = 10.8 Hz, Py-CH 2 -N), 3.27 (m, 2H, CH 3 -N-CH 2 ), 3.24 (m, 2H, Py-CH 2 -N-CH 2 ), 2.62 (d, 3H, 3 J PH = 12.4 Hz, N-CH 3 ). 13 C NMR (100 MHz, CDCl 3 , ppm): δ 157.30 (d, 3 J PC = 5.8 Hz, C 2 ), 149.07 (s, C 6 ), 137.08 (s, C 4 ), 122.53 (s, C 3 ), 122.11 (s, C 5 ), 50.29 (d, 2 J PC = 4.5 Hz, Py-CH 2 -N), 47.20 (d, 2 J PC = 13.6 Hz, Py-CH 2 -N-CH 2 ), 45.07(d, 2 J PC = 14.2 Hz CH 3 -N-CH 2 ), 30.86 (d, 2 J PC = 4.5 Hz, N-CH 3 ).…”

mentioning

confidence: 99%

“…HH = 4.4 Hz, H 6 ), 7.62 (dd, H,3 J HH = 7.6 Hz, HH = 8.8 Hz, 4 J HH = 1.6 Hz, H 4 ), 7.55 (d, H, HH = 7.6 Hz, H 3 ), 7.13 (dd, H,3 J HH = 4.4 Hz, HH = 8.8 Hz, 4 J HH = 1.6 Hz, H 5 ), 4.13 (d, 2H, PH = 8.0 Hz, Py-CH 2 -N), 3.62 [t, 3 J HH = 8.4, 8H, O-CH 2 (morp)], 3.50 [m, 8H, O-CH 2 (morp)], 3.46 (m, 2H, C 2 H 5 -N-CH 2 ), 3.16 (m, 2H, Py-CH 2 -N-CH 2 ), 3.09 [m, 8H, N-CH 2 (morp)], 3.02 [m, 8H, N-CH 2 (morp)], 2.89 (m, 2H, HH = 7.2 Hz, 3 J PH = 14.4 Hz N-CH 2 -CH 3 ), 1.16 (t, 3H, HH = 7.2 Hz, N-CH 2 -CH 3 ). 13 C NMR (100 MHz, CDCl 3 , ppm): δ 159.08 (d, 3 J PC = 8.5 Hz, C 2 ), 149.42 (s, C 6 ), 136.48 (s, C 4 ), 122.09 (s, C 3 ), 121.35 (s, C 5 ), 67.34 [(t, 3 J PC = 9.2 Hz, O-CH 2 (morp)], 67.22 [(t, 3 J PC = 8.4 Hz O-CH 2 (morp)], 51.46 (d, 2 J PC = 5.3 Hz, Py-CH 2 -N), 45.11 (d, 2 J PC = 10.3 Hz, Py-CH 2 -N-CH 2 ), 44.81 and 44.71 [s, N-CH 2 (morp)], 43.68 (d, 2 J PC = 11.5 Hz, C 2 H 5 -N-CH 2 ), 39.90 [(d, 2 J PC = 3.8 Hz, N-CH 2 -CH 3 ], 14.17 [(d, 3 J PC = 6.9 Hz, N-CH 2 -CH 3 ].…”

mentioning

confidence: 99%

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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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Section: Synthesis Of 4amentioning

confidence: 99%

Section: Synthesis Of 5amentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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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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Nanographene‐Doped Chalcone Derivatives of Dioxybiphenyl‐Bridged Dispirocyclotriphosphazenes: Synthesis, Electrical Properties, and DFT Calculations

et al. 2023

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The cyclotriphosphazenes, which constitute an important class of inorganic compounds, can show new properties in the medical or technological fields depending on the properties of the substituted organic/inorganic groups. Herein, we aimed to determine electrical and theoretical properties of the nanographene-doped chalcone derivatives of dioxybiphenyl-bridged dispiro-cyclotriphosphazenes. For this aim, a new series of chalcone substituted spiro-cyclotriphosphazenes (3 a-g) have been synthesized by the reaction of dioxybiphenyl-bridged dispiro-cyclotriphosphazene (3) with chalcone derivatives (1 ag), respectively. Then, nanographene was doped to these spirocyclotriphosphazene 3 a-g using a hydrothermal system. The dielectric constant and loss factor of 4 % graphene-doped chalcone-substituted spiro-cyclotriphosphazene 3 g were determined as 167 and 2147 at 1 kHz, respectively, showing a significant increase compared to compound 3 g. The energy values of HOMO and LUMO orbitals are computed using DFT theory's level of B3LYP/6-31G(d,p). The FMO's energy gap values for 3 a-g were found to be 7. 92, 3.48, 3.26, 3.33, 3.53, 4.03 and 3.75 eV, respectively. Especially at frequencies below 10 kHz, the most striking result was observed for the nanographenedoped 3 d. While the AC conductivity of 3 d at 1 kHz was 3.87 × 10 À 9 S cm À 1 , the conductivity of the graphene-doped 3 d was calculated as 5.00 × 10 À 6 S cm À 1 . In addition, DC conductivity measurements were completed as a function of temperature and linearly increasing graphs were obtained with temperature. The activation energies calculated from the slopes of these graphs were 0.293, 0.305, 0.364 and 0.920 eV for 3 c, 3 d, 3 e and 3 g, respectively.

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Phosphorus–nitrogen compounds: part 53—synthesis, characterization, cytotoxic and antimicrobial activity, DNA interaction and molecular docking studies of new mono- and dispirocyclotriphosphazenes with pendant arm(s)

et al. 2021

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Synthesis and spectroscopic characterizations of hexakis[(1-(4′-oxyphenyl)-3-(substituted-phenyl)prop-2-en-1-one)]cyclotriphosphazenes: theirin vitrocytotoxic activity, theoretical analysis and molecular docking studies

Cited by 17 publications

References 62 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

Nanographene‐Doped Chalcone Derivatives of Dioxybiphenyl‐Bridged Dispirocyclotriphosphazenes: Synthesis, Electrical Properties, and DFT Calculations

Phosphorus–nitrogen compounds: part 53—synthesis, characterization, cytotoxic and antimicrobial activity, DNA interaction and molecular docking studies of new mono- and dispirocyclotriphosphazenes with pendant arm(s)

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