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    Phosphorus-nitrogen compounds. Part 64. Comparative reactions of spiro and ansa (N/O) cyclotetraphosphazenes with bulky (4-fluorobenzyl) N/N and N/O donor type bidentate reagents: structure, stereogenic properties and cytotoxic activity studies
    (Royal Soc Chemistry, 2022) Elmas, Gamze; Binici, Arzu; Yakut, Mehtap; Okumus, Aytug; Kilic, Zeynel; Cosut, Bunyemin; Hokelek, Tuncer
    The reaction of octachlorocyclotetraphosphazene, N4P4Cl8 (1) (OCCP, tetramer), with an equimolar amount of sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (L1) resulted in the formation of ferrocenyl-spiro-(2) and ferrocenyl-2-cis-4-dichloro-ansa-(3) cyclotetraphosphazenes. Both of the starting compounds were used to produce the new inorganic-organic hybrid multiheterocyclic-spiro and ansa cyclotetraphosphazenes. Spiro (2) was treated with excess N-(4-fluorobenzyl)-N'-ethyl-1,2-diaminoethane (L2) to give 2-trans-6-dispiro (trans-2a) and 2-trans-4-cis-6-trans-8-tetraspiro (tetraspiro-2a) cyclotetraphosphazenes. Spiro (2) was also reacted with excess sodium 3-(4-fluorobenzylamino)-1-propanoxide (L3) to produce 2-trans-6-dispiro (trans-2b), 2-cis-6-dispiro (cis-2b), 2-cis-4-trans-6-trispiro (trans-2c), 2-cis-4-dispiro-6-trispiro (cis-2c), 2-cis-4-dichloro-ansa-4-trans-6-spiro(N/O) (ansa-2b) and 2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (ansa-2c). The reactions of 2,4-ansa (3) with excess L2 led to the formation of 2-cis-4-dichloro-ansa-2-trans-6-spiro(N/N) (trans-3a) and 2-cis-4-dichloro-ansa-2-cis-6-spiro(N/N) (cis-3a) cyclotetraphosphazenes. However, the reactions of 2,4-ansa (3) with excess L3 afforded monospiro {2-cis-4-dichloro-ansa-4-trans-6-spiro(N/O) (trans-3b) and 2-cis-4-dichloro-ansa-4-cis-6-spiro(N/O) (cis-3b)} and dispiro {2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (trans-3c) and 2-cis-4-dichEoro-ansa-6-cis-8-dispiro(N/O) (cis-3c)}. The obtained products were characterized by spectroscopic techniques. The crystal structures of trans-2b and cis-3b were clarified by single crystal X-ray analysis. The products had stereogenic P-centres except for trans-2a, tetraspiro-2a, trans-2b and cis-2b. The stereogenic properties of tetrameric phosphazenes were evaluated by X-ray crystallography and chiral high performance liquid chromatography (HPLC) methods. The structure of cis-3b revealed the absolute configurations of the enantiomers (SS'R ''/RR'S ''). The broad HPLC peak of cis-3b indicates that it may exist as a resamate in solution. The cytotoxic activities of the cyclotetraphosphazenes were evaluated using an MTT assay against L929 mouse fibroblasts, A549 non-small lung cancer and Caco-2 colorectal adenocarcinoma cells. Compound cis-3b was found to be very effective in all cell lines up to 104.1 mu M.
  • [ X ]
    Öğe
    Phosphorus-nitrogen compounds: part 68. Synthesis, characterization, stereogenism, photophysical and bioactivity studies of novel unsymmetrical dispiro(N/N)cyclotriphosphazenes with carbazolyl and 4-chlorobenzyl pendant arms
    (Royal Soc Chemistry, 2023) Cemaloglu, Resit; Asmafiliz, Nuran; Kilic, Zeynel; Cosut, Bunyemin; Sabah, Busra Nur; Acik, Leyla; Cerci, Nebahat Aytuna
    Organic-inorganic hybrid multi-heterocyclic unsymmetrical cis/trans dispirocyclotriphosphazenes with different pendant arms were obtained and their spectral, stereogenic, photophysical and bioactivity properties were investigated. To prepare these phosphazenes, the starting compounds tetrachloro(4-chlorobenzyl)spiro(N/N)cyclotriphosphazenes, (ClBzSpiro-5)R-1(N3P3)Cl-4 [Bz: Benzyl; R-1: Me (1) and R-1: Et (2)], were prepared regioselectively from the reactions of hexachlorocyclotriphosphazene, N3P3Cl6 (HCCP, trimer) with N-methyl/ethyl-N'-(4-chlorobenzyl)-1,2-diaminoethanes. Reactions of tetrachlorocyclotriphosphazenes (1 and 2) and 9-ethyl-N-methyl-3-carbazolyl-1,2-diaminoethane (3) or 9-ethyl-N-methyl-3-carbazolyl-1,3-diaminopropane (4) produce new cis/trans-dispirocyclotriphosphazenes, [(ClBzSpiro-5)R-1(N3P3)(CzSpiro-n)R-2]Cl-2 (Cz: Carbazolyl; R-1, R-2: Me or Et; n = 5 or 6; (5a-8a and 5b-8b), containing unsymmetrical spiro-architectures. In addition, the structures of trans-7a and cis-7b isomers were clarified by single crystal X-ray crystallography. The chiralities of trans-7a and cis-7b were confirmed using X-ray crystal structures, P-31 NMR spectra recorded upon the addition of chiral solvating agent [(S)-(+)-2,2,2-trifluoro-1-(9 & PRIME;-anthryl)ethanol; CSA], and circular dichroism (CD) spectra. Moreover, the photophysical properties of phosphazenes showed a fluorescence profile with lifetimes of about 4.9-6.6 ns and quantum yields in the range of 0.10-0.14. Additionally, the antibacterial and antifungal activities of the newly synthesized phosphazenes against some bacteria and yeast strains and their interactions with pBR322 plasmid DNA were investigated. The bacterial strain most susceptible (MIC = 156.3 mu M) to compounds 5a and 8a was P. aeruginosa. However, it was found that the yeast strain most susceptible (MIC = 156.3 mu M) to compounds 5b, 7a, 7b and 8b was C.albicans. The cytotoxic activities of 5a, 5b, 7b and 8a against L929 fibroblast and MCF-7 breast cancer cells were determined. However, cis-5b showed reasonable antioxidant activity with a radical scavenging value of 35.20%.
  • Küçük Resim
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    Structural and computational characterization of 4 ',4 ',6 ',6 '-tetrachloro-3-(2-methoxyethyl)-3H,4H-spiro-1,3,2-benzoxaza phosphinine-2,2 '-[1,3,5,2,4,6]triazatriphosphinine
    (Elsevier, 2016) Isiklan, Muhammet; Yildirim, Erdem Kamil; Atis, Murat; Sonkaya, Omer; Cosut, Bunyemin
    In this study a new monospirocyclic phosphazene derivative, 4',4',6',6'-tetrachloro-3-(2-methoxyethyl)3H,4H-spiro [1,3,2-benzoxazaphosphinine-2,2'- [1,3,5,2,4,6] triazatriphosphinine] (SP1) was synthesized from the reaction of hexachlorocyclotriphosphazene (N3P3CI6) with N/0 donor-type, 2-{[(2-Metoxyethyl) amino]methylphenol. The structural investigations of the compound were verified by elemental analyses, MS, FFIR, 1H, 13C, 11 --P NMR spectroscopy and the single crystal X-ray diffraction analysis. The structural and spectroscopic data of the molecule in the ground state were calculated by using density functional method (DFT) using 6-311++G (d, p) basis set. The complete assignments of all vibrational modes were performed on the basis of the total energy distributions (TED). Isotropic chemical shifts (31P, 1H and 13C NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. Theoretical calculations of bond parameters, harmonic vibration frequencies and nuclear magnetic resonance are in good agreement with experimental results. The electrophilic and nucleophilic attack centers in SP1 were predicted with the local softness values (sit, and si) of individual atoms and it is confirmed that P atoms of the PCl2 groups are nucleophilic attack centers. (C) 2016 Elsevier B.V. All rights reserved.
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    Synthesis of Bis(2,2,3,3-tetrafluoro-1,4-butanedialkoxy)-2-trans-6-bis(4-fluorobenzyl)spirocyclotetraphosphazene: Structural Characterization, Biological Activity and DFT Studies
    (SPRINGER/PLENUM PUBLISHERS, 2020) Elmas, Gamze; Kilic, Zeynel; Cosut, Bunyemin; Kesan, Gurkan; Acik, Leyla; Cam, Merve; Tunali, Beste Cagdas
    The Cl replacement reaction of octachlorocyclotetraphosphazene, N4P4Cl8 (1), with two equimolar amounts of N-(4-fluorobenzyl)-N'-methylpropane-1,3-diamine led to the formation of 4,4,8,8-tetrachloro-2-trans-6-bis-N-(4-fluorobenzyl)-N'-methylpropane-1,3-diamino-cyclotetraphosphazene (2). The reaction of 2 with excess sodium 2,2,3,3-tetrafluoro-1,4-butanedioxide afforded the bis(2,2,3,3-tetrafluoro-1,4-butanedialkoxy)-2-trans-6-bis(4-fluorobenzyespirocyclotetraphosphazene (2a). The elemental analyses, mass spectrum (ESI-MS), FTIR, HSQC, HMBC, H-1, C-13 and P-31 NMR spectral data of 2a were consistent with the proposed structure. The crystal structure of 2a was elucidated by X-ray diffraction method. The spectroscopic data of the molecules (2 and 2a) in the ground state were investigated by the Density Functional Theory (DFT) from the crystal structures. On the other hand, compound 2a was found to be the most active against S. aureus G(+) (MIC value: 125 mu M). Whilst, any antifungal activity of 2a was not observed against C. albicans and C. tropicalis. This compound also exhibits cytotoxic activity against L929 fibroblast and MCF-7 breast cancer cells. The interaction of 2a with pBR322 DNA was researched using gel electrophoresis. It is understood that the change in DNA conformation by interstrand of 2a with A/A and G/G nucleobases in DNA. [GRAPHICS] .