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    Phosphorus-nitrogen compounds. Part 35. Syntheses, spectroscopic and electrochemical properties, and antituberculosis, antimicrobial and cytotoxic activities of mono-ferrocenyl-spirocyclotetraphosphazenes
    (Royal Soc Chemistry, 2016) Okumus, Aytug; Elmas, Gamze; Cemaloglu, Resit; Aydin, Betul; Binici, Arzu; Simsek, Hulya; Acik, Leyla
    The reactions of octachlorocyclotetraphosphazene, N4P4Cl8, with N-alkyl-N-mono-ferrocenyldiamines, FcCH(2)NH(CH2)(n)NHR1 [n = 2, Fc = ferrocene, R-1 = Me (1); n = 2, R-1 = Et (2) and n = 3, R-1 = Me (3)], led to the formation of monoferrocenyl-spirocyclotetraphosphazenes (4-6). When the reactions were carried out with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5] decane (DASD), the fully substituted products (4a-6c) were obtained in high yields. The structures of all the phosphazene derivatives were characterized by MS, FTIR, H-1, C-13 and P-31 NMR, HSQC and HMBC techniques. The crystal structures of 4a and 5a were determined by X-ray crystallography. The electrochemically reversible one-electron oxidation of Fc redox centers was observed for cyclotetraphosphazenes. The fully substituted phosphazenes (4a-6c) were evaluated for their antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv, and compounds 4a-6a and 5c were found to be active. The antibacterial activities of phosphazenes 4a-6c against G(+) and G(-) bacteria and their antifungal activities against yeast strains were carefully scrutinized. The results indicate that compounds 4a-6a, 6b, 4c and 5c are very effective against yeast strains. The anticandidal activities of 6a and 6b make them promising anticandidal agents. The interactions of these compounds with plasmid DNA and their cytotoxic activity against L929 fibroblast and DLD-1 colon cancer cell lines were also investigated.
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    Phosphorus-nitrogen compounds. Part 42. The comparative syntheses of 2-cis-4-ansa(N/O) and spiro(N/O) cyclotetraphosphazene derivatives: spectroscopic and crystallographic characterization, antituberculosis and cytotoxic activity studies
    (Royal Soc Chemistry, 2019) Binici, Arzu; Okumus, Aytug; Elmas, Gamze; Kilic, Zeynel; Ramazanoglu, Nagehan; Acik, Leyla; Simsek, Hulya
    The reaction of N4P4Cl8 (1) with one equimolar amount of the sodium salt of an N/O donor-type bidentate ligand (2) afforded two kinds of derivatives, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa- (2,4-ansa; 3) and mono-ferrocenyl-spiro- (spiro; 4) hexachlorocyclotetraphosphazenes. The reaction yield (35%) of 4 was significantly larger than that of 3 (14%). The 2,4-ansa compound (3) was reacted with excess secondary amines to produce 2-cis-4-dichloro-ansa-cyclotetraphosphazenes (3a-3d). On the other hand, the spiro compound (4) gave fully substituted mono-ferrocenyl-spiro-cyclotetraphosphazenes (4a-4d) with excess monoamines as well. The tetrameric phosphazene derivatives were characterized by ESI-MS and/or HRMS, FTIR, HSQC, HMBC, H-1, C-13, and P-31 NMR spectroscopy and X-ray crystallography (for 4). It is observed that the 2,4-ansa and spiro-cyclotetraphosphazenes have different thermal stabilities. Additionally, the CVs of the new mono-ferrocenyl pendant-armed cyclotetraphosphazenes revealed electrochemically reversible one-electron oxidation of the Fe-redox centre. The 2,4-ansa phosphazenes (3 and 3a-3d) have two different stereogenic P centers indicating that they are expected to be in racemic mixtures (RR'/SS'). The chiralities of 3a and 3c were investigated by chiral HPLC. The manuscript also deals with the antimicrobial activities against G(+)/G(-) bacteria and fungi, the interactions with plasmid DNA, the in vitro cytotoxic activities against L929 fibroblast and MCF7 breast cells, and the antituberculosis activities against Mycobacterium tuberculosis H37Rv of the cyclotetraphosphazenes.
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    Phosphorus-nitrogen compounds: Part 60: Synthesis of hexaminomonoferrocenyl-spiro(N/O)cyclotetraphosphazenes: Spectral and electrochemical properties, tuning of redox feature, and antituberculosis activity
    (Taylor & Francis Ltd, 2023) Binici, Arzu; Elmas, Gamze; Okumus, Aytug; Guzel, Remziye; Simsek, Hulya; Kilic, Zeynel
    In the present investigation, the condensation reaction of octachlorocyclotetraphosphazene, N4P4Cl8 (1) (tetramer, OCCP), with sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (L) resulted in the formation of the starting compound hexachloromonoferrocenylspiro(N/O)cyclotetraphosphazene (2). Thereafter, reactions of spiro (2) with excesses of 1-(2-aminoethyl)pyrrolidine, 1-(2-aminoethyl)piperidine and 4-(2-aminoethyl)morpholine in dry THF gave hexaaminomono-ferrocenylspiro(N/O)cyclotetraphosphazenes, 2a, 2b, and 2c, respectively. These new products were prepared for investigation of spectral and electrochemical properties, tuning of redox features, and examination of antituberculosis activities. The structures of 2a-2c were elucidated using elemental analysis, mass spectrometry (ESI-MS), FTIR, HMBC, HSQC, H-1, C-13 {H-1}, and P-31 {H-1} NMR data. The electrochemical behavior of these products containing monoferrocenyl group was investigated. Their use as potential alternative electrolyte redox couples for dye-sensitized solar cells (DSSC) was examined. The findings may inspire solar cell studies to explore the redox mediator behind the working mechanisms of DSSCs. Conversely, the antituberculosis activities of three compounds were examined against Mycobacterium tuberculosis H37Rv. The MIC values of 2a and 2 b were found to be as 30 and 35 mu g/mL, respectively, against the H37Rv reference strain.