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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; Okumuş, Aytuğ; Kilic, Zeynel; Coşut, Bünyemin; Hökelek, 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.
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    The reactions of N3P3Cl6 with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes
    (2017) Okumuş, Aytuğ; Elmas, Gamze; Kılıç, Zeynel; Ramazanoğlu, Nagehan; Açık, Leyla; Türk, Mustafa; Akca, Gülçin
    The Cl replacement reactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazene (2) with excess monoamines led to the formation of 4-fluorobenzylspiro(N/O)tetraaminocyclotriphosphazenes (2a2d). The partly substituted dispiro 3b and dispiro 3c and fully substituted trispirocyclotriphosphazenes (trans 4a, cis 4c, 4d, and 4e) were obtained, respectively, from the reactions of 2 with one equimolar and two equimolar amounts of diamines, aminoalcohol, and diols. Although efforts were made for the separation of the cis/trans and optical isomers of the dispiro phosphazenes, only one set of diastereomers (RR/RS or SS/SR) of dispiro 3b and dispiro 3c was isolated, respectively. The 31P NMR spectral data of the other dispiro phosphazenes were evaluated from the 31P NMR spectra of the reaction mixtures. The reactions of 2 with excess N-methylethylenediamine gave trans 4a as a racemic mixture. While trans 4b (racemic) and cis 4b (meso) occurred from the reaction of 2 with excess N-methyl-1,3-propanediamine, they were not isolated separately. Some of the phosphazenes were screened against bacteria and fungi. The activities of the compounds against anaerobic and microaerophilic gram-negative bacteria were evaluated. It was found that compounds 2, 2b, and trans 4a exhibited tolerable toxic effects on fibroblast cells and had the highest toxicity against MCF-7 cells
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    The comparative reactions of 2-cis-4-ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies
    (Wiley, 2021) Okumuş, Aytuğ; Elmas, Gamze; Kilic, Zeynel; Binici, Arzu; Ramazanoglu, Nagehan; Açık, Leyla; Coşut, Bünyemin
    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 P-31 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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    The reactions of N$_{3}$P$_{3}$Cl$_{6}$ with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes
    (Tubitak Scientific & Technological Research Council Turkey, 2017) Okumuş, Aytuğ; Elmas, Gamze; Kilic, Zeynel; Ramazanoglu, Nagehan; Açık, Leyla; Türk, Mustafa; Akça, Gülçin
    The Cl replacement reactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazene (2) with excess monoamines led to the formation of 4-fluorobenzylspiro(N/O)tetraaminocyclotriphosphazenes (2a-2d). The partly substituted dispiro 3b and dispiro 3c and fully substituted trispirocyclotriphosphazenes (trans 4a, cis 4c, 4d, and 4e) were obtained, respectively, from the reactions of 2 with one equimolar and two equimolar amounts of diamines, aminoalcohol, and diols. Although efforts were made for the separation of the cis/trans and optical isomers of the dispiro phosphazenes, only one set of diastereomers (RR/RS or SS/SR) of dispiro 3b and dispiro 3c was isolated, respectively. The P-31 NMR spectral data of the other dispiro phosphazenes were evaluated from the P-31 NMR spectra of the reaction mixtures. The reactions of 2 with excess N-methylethylenediamine gave trans 4a as a racemic mixture. While trans 4b (racemic) and cis 4b (meso) occurred from the reaction of 2 with excess N-methyl-1,3-propanediamine, they were not isolated separately. Some of the phosphazenes were screened against bacteria and fungi. The activities of the compounds against anaerobic and microaerophilic gram-negative bacteria were evaluated. It was found that compounds 2, 2b, and trans 4a exhibited tolerable toxic effects on fibroblast cells and had the highest toxicity against MCF-7 cells.