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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; Kılıç, Zeynel; Binici, Arzu; Ramazanoğlu, Nagehan; Açık, Leyla; Çoşut, Bünyemin; Güzel, Remziye; 0000-0002-2169-5695; 0000-0003-4877-3697; 0000-0003-1061-8122; 0000-0001-7470-4156; 0000-0003-0541-9129; 0000-0002-3672-8429; 0000-0001-6530-0205; 0000-0002-5781-6049
    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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    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 72. Bisspiro(N/N) cyclotri-phosphazenes with 4-chlorobenzyl and ferrocenyl pendant arms: Synthesis, structural characterization, dye-sensitized solar cell fabrication and antituberculosis activity studies
    (Elsevier, 2024) Berberoglu, Ipek; Cemaloglu, Resit; Binici, Arzu; Yakut, Mehtap; Asmafiliz, Nuran; Kilic, Zeynel; Guzel, Remziye
    In this study, dichlorobisspiro(N/N)cyclotriphosphazenes with 4-chlorobenzyl and ferrocenyl-pendant arms were prepared to investigate their spectroscopic and crystallographic characterizations, and antituberculosis activities. The chlorine replacement reactions of tetrachloro(4-chlorobenzyl)spiro(N/N)cyclotri-phosphazenes with ferrocenyldiamines (4 and 5) lead to dichlorobispiro(N/N)cyclotriphosphazenes, containing unsymmetrical diaminospirorings. All cyclotriphosphazenes were characterized by mass spectrometry, FTIR and 31P NMR spectroscopies. Two different stereogenic P-centers are present in the unsymmetrically substituted inorganicorganic fused hybrid rings. These compounds may be in the form of racemic mixtures (RR'/SS' and RS'/SR'). The molecular and crystal structures of trans (6a and 7a) and cis (6b and 7b) isomers were elucidated by singlecrystal X-ray structural crystallography. The space groups of trans-6a, cis-6b, trans-7a and cis-7b are centrosymmetric P -1, P bca, P 21/n and P bca, respectively. Therefore, the crystal lattices contain both enantiomers. The absolute configurations of P2 atoms of 6a, 6b, 7a and 7b are R, R, S and S, respectively. It was determined that the most effective compound was 6b against Mycobacterium tuberculosis H37Rv (ATCC 27,294) strain among the phosphazenes 6a, 6b and 10b. Among the compounds, In the reversible cyclic voltammograms of ferrocenyldispirophosphazenes, only one oxidation-reduction wave was observed. The HOMO energy values of the compounds were figured out using the oxidation potential (Eox). Whereas, the LUMO energy values were figured out from the optical band gap values using Tauc plots. In addition, it was determined that the most effective compound that can be used in dye-sensitized solar cells (DSSCs) is cis-11b.
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    Phosphorus-nitrogen compounds. Part 72. Bisspiro(N/N)cyclotri-phosphazenes with 4-chlorobenzyl and ferrocenyl pendant arms: Synthesis, structural characterization, dye-sensitized solar cell fabrication and antituberculosis activity studies
    (Elsevier B.V., 2024) Berberoğlu, İpek; Cemaloğlu, Reşit; Binici, Arzu; Yakut, Mehtap; Asmafiliz, Nuran; Kılıç, Zeynel; Güzel, Remziye; 0000-0002-2802-0754; 0000-0001-7470-4156; 0000-0002-9335-4101
    In this study, dichlorobisspiro(N/N)cyclotriphosphazenes with 4-chlorobenzyl and ferrocenyl-pendant arms were prepared to investigate their spectroscopic and crystallographic characterizations, and antituberculosis activities. The chlorine replacement reactions of tetrachloro(4-chlorobenzyl)spiro(N/N)cyclotri-phosphazenes with ferrocenyldiamines (4 and 5) lead to dichlorobispiro(N/N)cyclotriphosphazenes, containing unsymmetrical diaminospirorings. All cyclotriphosphazenes were characterized by mass spectrometry, FTIR and 31P NMR spectroscopies. Two different stereogenic P-centers are present in the unsymmetrically substituted inorganic-organic fused hybrid rings. These compounds may be in the form of racemic mixtures (RR'/SS' and RS'/SR'). The molecular and crystal structures of trans (6a and 7a) and cis (6b and 7b) isomers were elucidated by single-crystal X-ray structural crystallography. The space groups of trans-6a, cis-6b, trans-7a and cis-7b are centrosymmetric P -1, P bca, P 21/n and P bca, respectively. Therefore, the crystal lattices contain both enantiomers. The absolute configurations of P2 atoms of 6a, 6b, 7a and 7b are R, R, S and S, respectively. It was determined that the most effective compound was 6b against Mycobacterium tuberculosis H37Rv (ATCC 27,294) strain among the phosphazenes 6a, 6b and 10b. Among the compounds, In the reversible cyclic voltammograms of ferrocenyl-dispirophosphazenes, only one oxidation–reduction wave was observed. The HOMO energy values of the compounds were figured out using the oxidation potential (Eox). Whereas, the LUMO energy values were figured out from the optical band gap values using Tauc plots. In addition, it was determined that the most effective compound that can be used in dye-sensitized solar cells (DSSCs) is cis-11b.
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    Phosphorus-nitrogen compounds. Part 77. The synthesis of novel ferrocenyl(N/O)spiro- and 2-cis-4-dichloro-ferrocenyl(N/O)ansa-cyclotetraphosphazenes with 9-ethyl-3-carbazolyl pendant arm(s): spectral, bioactivity, electrochemical and dye-sensitized solar cell fabrication studies
    (Taylor & Francis Ltd, 2025) Mutlu, Gurcu; Yakut, Mehtap; Okumus, Aytug; Elmas, Gamze; Binici, Arzu; Guzel, Remziye; Sabah, Busra Nur
    Herein, the reactions of octachlorocyclotetraphosphazene (OCCP, 1) with sodium-3-ferrocenylmethyl-amino)-1-propanoxide (L1) gave hexachloro-ferrocenyl-(N/O)-spiro-2 and 2-cis-4-dichloro-ferrocenyl-(N/O)-ansa-3 cyclotetraphosphazenes in THF. Spiro- (2) reacted with excess 9-ethyl-N-methyl-3-carbazolyl-1,3-diaminopropane (L2) and 9-ethyl-N-ethyl-3-carbazolyl-1,2-diaminoethane (L3) to produce 2-trans-6-dispiro (dispiro-2a) and 2-trans-4-cis-6-trans-8-tetraspiro (tetraspiro-2b) cyclotetraphosphazenes, respectively. The reactions of ansa-3 with excess L2 led to the formation of monospiro {2-cis-4-dichloro-ansa-2-trans-6-spiro(N/N) (ansa-spiro-3b)} and dispiro {2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/N) (ansa-dispiro-3b)} cyclotetraphosphazenes. However, the reactions of ansa-3 with excess 9-methyl-N-ethyl-3-carbazolyl-1,2-diaminomethane (L4) afforded 2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/N) (ansa-dispiro-3a). Ansa-3 was also reacted with excess sodium 3-(9-ethyl-carbazolamino)-1-propanoxide (L5) to give 2-cis-4-dichloro-ansa-2-trans-6-spiro(N/O) (ansa-spiro-3c) and 2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (ansa-dispiro-3c) cyclotetraphosphazenes. Reactions were carried out by classical and microwave-assisted methods. These novel multi-heterocyclic inorganic/organic hybrid cyclotetraphosphazenes can offer valuable insights into developing new materials. Tetraspiro-2b and all ansa compounds have more than one stereogenic P-atom. The optical and electrochemical properties of some cyclotetraphosphazenes were investigated using UV-vis absorption and cyclic voltammetry (CV) techniques. As a result, these phosphazenes can be suggested as ferrocene-based charge transformable structures. They can be used as new-generation and synergistic dye-sensitized solar cell (DSSC) materials. Additionally, antimicrobial activities of five compounds (dispiro-2a, ansa-spiro-3b, ansa-dispiro-3b, ansa-spiro-3c and ansa-dispiro-3c) against various pathogenic bacteria and yeasts were evaluated. Their interactions with pBR322 plasmid DNA were also investigated.
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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.
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    Phosphorus-nitrogen compounds: part 71. Novel unsymmetrically-substituted dispiro-cyclotriphosphazenes: synthesis, characterization, antituberculosis activity, and phototunable charge storage studies
    (Royal Soc Chemistry, 2023) Cemaloglu, Resit; Berberoglu, Ipek; Yakut, Mehtap; Binici, Arzu; Asmafiliz, Nuran; Kilic, Zeynel; Guzel, Remziye
    The aim of this research is to synthesize and characterize new organic-inorganic hybrid multi-heterocyclic dichlorodispiro(N/N)cyclotriphosphazenes and to elucidate their antituberculosis activities. To achieve this aim, primarily, trans (6a-11a) and cis (6b-11b) unsymmetrical dichlorodispiro(N/N)cyclotriphosphazenes were obtained from ferrocenyldiamines (4 and 5) and benzyl-pendant armed tetrachloromonospirophosphazenes as starting materials. Several spectroscopic techniques (mass spectrometry, FTIR, and 1H, 13C, and 31P NMR), as well as elemental analysis, were employed to characterize the new phosphazenes. All unsymmetrically substituted phosphazenes are expected to be racemic mixtures (RR '/SS ' and RS '/SR ') due to two different stereogenic P-centers. In addition, the molecular and crystal structures of cis-6b, cis-10b, and cis-11b isomers were elucidated via single-crystal X-ray crystallography. They belong to centrosymmetric C2/c, P21/c, and P1 space groups, respectively; thus, their crystal lattices must contain both the enantiomers, RR '/SS ' or SR '/RS '. Moreover, only one oxidation-reduction wave was observed for the ferrocenyl-dispirophosphazenes in the reversible cyclic voltammograms. The HOMO and LUMO energy values of the phosphazenes were calculated using the oxidation potential (Eox) and the optical band gap values using Tauc plots, respectively. To determine the phototunable charge storage properties of the four dispirophosphazenes, their memory functions were investigated under UV illumination. The antituberculosis activities of the dichlorodispiro(N/N)cyclotriphosphazenes trans-6a, cis-6b, trans-10a, and cis-10b against Mycobacterium tuberculosis H37Rv (ATCC 27294) strain were evaluated. The results showed that among these compounds, trans-6a (MIC value 18 mu g mL-1) was much more effective than the other phosphazenes. Unsymmetrical cis/trans dispirocyclotriphosphazenes were prepared. The electrochemical behaviors and phototunable charge storage properties of the compounds were determined. The antituberculosis activities were examined against M. tuberculosis H37Rv.