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Öğe Dispiro-4-bromobenzylaminophosphazenes: Synthesis reactions, spectroscopic and chromatographic properties, crystal structures, biological, and cytotoxic activities(Amer Chemical Soc, 2019) Kuzey, Nur Guven; Ozgur, Mehtap; Asmafiliz, Nuran; Acik, Leyla; Aydin, Betul; Hokelek, Tuncer; Cerci, Aytuna…Öğe Dispiro-4-bromobenzylaminophosphazenes: Synthesize reactions, spectroscopic properties, crystal structures, biological and cytotoxic activities(Amer Chemical Soc, 2019) Kuzey, Nur Guven; Ozgur, Mehtap; Asmafiliz, Nuran; Acik, Leyla; Aydin, Betul; Hokelek, Tuncer; Cerci, Nebahat Aytuna…Öğe Novel phosphazene derivatives: Synthesis, anisochronism and structural investigations of mono- and ditopic spiro-crypta phosphazenes(Elsevier, 2007) Asmafiliz, Nuran; İlter, Elif Ece; Isıklan, Muhammet; Kilic, Zeynel; Tercan, Baris; Caylak, Nagihan; Büyükgüngör, OrhanThe reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N2O2-donor type coronands (diaza-crown ethers) 1-3 afford novel monotopic 4-7 and ditopic 8-10 spiro-crypta phosphazenes, respectively. It has been observed that the reactions of N3P3Cl6 with I equivalent amount of coronands 1-3 yield only monotopic spiro-derivatives, while three equivalent amount of coronands 2 and 3 give dominantly ditopic dispiro-crypta-phosphazene skeletons. On the other hand, the P-31 NMR spectrum of 8 indicates that the ditopic spiro-ansa phosphazene 10 is present besides the ditopic dispiro derivative 8. Unexpectedly, the reaction of 6 with excess amount of pyrrolidine leads to the formation of geminal product 7. The P-31 NMR spectra of 4, 5, 6 and 10 indicate that all of these compounds have anisochronism. The structures of 5, 8 and 9 have been determined by X-ray crystallography. The relative radii of macrocyclic hole sizes of 5, 8 and 9 are calculated from the crystallographic results. The relationships between the exocyclic NPN and endocyclic NPN bond angles of the analogous compounds with delta P-shifts of NPN phosphorus atoms have been discussed. Thus, sums of the bond angles around the nitrogen atoms are in the range of [342.7(2)degrees-354.4(2)degrees], showing that the nitrogen atoms have pyramidal configurations. The pyramidal configuration gives rise to stereogenic properties. The salient spectroscopic features [FTIR, H-1, C-13, P-31 NMR, HETCOR (for 5 and 7) and MS] of all the compounds are presented. (c) 2006 Elsevier B.V. All rights reserved.Öğe Phosphorus nitrogen compounds: Part 34. Syntheses, structural investigations, cytotoxic and biological activities of spiro-ansa-spiro and spiro-bino-spiro tetrameric phosphazene derivatives(Elsevier Science Sa, 2016) Berberoglu, Ipek; Asmafiliz, Nuran; Kilic, Zeynel; Hokelek, Tuncer; Koc, L. Yasemin; Acik, Leyla; Dal, HakanThe reactions of N4P4Cl8 with the symmetric N2N2 (1-3) and N2O2 (4) bulky ligands gave partly substituted 2,4-sas (5 and 6), 2,6-sas (7-10) and sbs (11-14) tetrameric phosphazene derivatives. The 2,4-sas-5, 2,6-sas-8 and sbs-12 reacted with pyrrolidine to give fully-substituted tetra-(15 and 16) and dode-capyrrolidinocyclotetraphosphazenes (17-19). The structures of all the phosphazenes were verified by FTIR, MS, H-1, C-13{H-1} and P-31{H-1} NMR, and HSQC spectral data. The crystal structures of 7, 9 and 10 were examined by single crystal X-ray diffraction techniques. The compounds 1-3, 5, 8, 9, 12, 13, 16 and 18 were screened for antimicrobial activity against G(+) and G(-) bacteria and fungi. The compound 16 is found to possess excellent activity (MIC values of 39 and 78 mu M) against fungal pathogen Candida krusei and Candida albicans. Meanwhile, interactions between pBR322 plasmid DNA and 1-3, 5, 8, 9, 12, 13, 14, 16 and 18 were investigated by agarose gel electrophoresis. The compounds 5, 8, 9, 12, 13, 16 and 18 were appraised for their cytotoxic activity against L929 Fibroblast and MDA-MB-231 breast cancer cell lines. Compounds 13 and 16 are as effective as cis-platin. (C) 2016 Elsevier B.V. All rights reserved.Öğe Phosphorus-nitrogen compounds. 14. Synthesis, stereogenism, and structural investigations of novel N/O spirocyclic phosphazene derivatives(Amer Chemical Soc, 2007) İlter, Elif Ece; Asmafiliz, Nuran; Kılıç, Zeynel; Işıklan, Muhammet; Hökelek, Tuncer; Çaylak, Nagihan; Şahin, ErtanThe reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N/O donor-type N-alkyl-o-hydroxybenzyl- and o-hydroxynaphthylamines result in novel mono-(3a, 4a and 4b), di- (5a and 5b), and tri- (3b, 6a, and 6b) spirocyclic phosphazene derivatives. The tetrakis-pyrrolidinophosphazene, 3b, has been obtained from the reaction of partly substituted compound 3a with the excess pyrrolidine in tetrahydrofuran. The relationship between the endocyclic NPN (alpha) and exocyclic NPO (alpha') bond angles of the analogous spirocyclic phosphazenes with the delta P shifts of NPO phosphorus atoms have been presented. It was observed that there is a linearity between alpha angles and delta P shifts, while no linear relationship has been observed for alpha' angles. In addition, we have found the correlation between Delta(P-N) and delta(NPO) shifts, which implies a linear relationship. Delta(P-N) = (a-b), where a and b are the average lengths of two adjacent P-N bonds. The structural investigations of all of the compounds have been made by elemental analyses; mass spectrometry; Fourier transform infrared spectroscopy; one-dimensional H-1, C-13, and P-31 NMR; distortionless enhancement by polarization transfer; and two-dimensional correlation spectroscopy, heteronuclear shift correlation, and heteronuclear multiple-bond correlation homo- and heteronuclear correlation techniques. The solid-state structures of 3a, 4a, 4b, and 5a have been determined by X-ray crystallographic techniques. The asymmetric units of compounds 3a and 4a contain two independent molecules, and 3a has strong intermolecular N-H center dot center dot center dot N hydrogen bonds linking three phosphazene rings. The molecular structure of 6a looks like a propeller where the chemical environment of P1 is different from that of P2 and P3. On the other hand, compounds 5a and 5b are expected to exist as cis- or trans-geometric isomers and to be in cis (meso) or trans (racemic) configurations. The crystallographic and preliminary chiral solvating agents results show that both of them are trans (racemic). In addition, 6a and 6b are also expected to exist as cis-trans-trans- and cis-cis-cis-geometric isomers; both of them are found to be in cis-trans-trans geometries. According to the two-dimensional spectroscopic data, the possible conformations of 3a and 4a in CDCl3 are the same with the solid-state structures.Öğe Phosphorus-Nitrogen Compounds. 21. Syntheses, Structural Investigations, Biological Activities, and DNA Interactions of New N/O Spirocyclic Phosphazene Derivatives. The NMR Behaviors of Chiral Phosphazenes with Stereogenic Centers upon the Addition of Chiral Solvating Agents(Amer Chemical Soc, 2010) Işıklan, Muhammet; Asmafiliz, Nuran; Özalp, Ezgi Elif; İlter, Elif Ece; Kılıç, Zeynel; Çoşut, Bünyemin; Akyüz, EmelThe reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N/O-donor-type N-alkyl (or aryl)-o-hydroxybenzylamines (la-le) produce mono- (2a-2e), di- (3a-3d), and tri- (4a and 4b) spirocyclic phosphazenes. The tetrapyrrolidino monospirocyclic phosphazenes (2f-2i) are prepared from the reactions of partly substituted compounds (2a-2d) with excess pyrrolidine. The dispirodipyrrolidinophosphazenes (3e-3h) and trispirophosphazenes (3i-3k) are obtained from the reactions of trans-dispirophosphazenes with excess pyrrolidine and sodium (3-amino-1-propanoxide), respectively. Compounds 3a-3d have cis and trans geometric isomers. Only the trans isomers of these compounds are isolated. Compounds 3a-3h have two stereogenic P atoms. They are expected to be in cis (meso) and trans (racemic) geometric isomers. In the trans trispiro compounds (3i-3k), there are three stereogenic P atoms. They are expected to be in racemic mixtures. The stereogenic properties of 3a-3k are confirmed by P-31 NMR spectroscopy upon the addition of the chiral solvating agent; (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol. The molecular structures of 3i-3k, 4a, and 4b look similar to a propeller, where the chemical environment of one P atom is different from that of others. Additionally, 4a and 4b are also expected to exist as cis-trans-trans and cis-cis-cis geometric isomers, but both of them are found to be in cis-trans-trans geometries. The solid-state structures of 2a, 2e, 2f, 3e, and 31 are determined by X-ray crystallography. The compounds 2f-2i, 3e-3i, and 3k are screened for antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against yeast strains. These compounds (except 3f) have shown a strong affinity against most of the bacteria. Minimum inhibitory concentrations (MIC) are determined for 2f-2i, 3e-3i, and 3k. DNA binding and the nature of interaction with pUC18 plasmid DNA are studied. The compounds 2f-2i, 3e-3i, and 3k induce changes on the DNA mobility. The prevention of BamHI and HindIII digestion (except 2g) with compounds indicates that the compounds bind with nucleotides in DNA.Öğe Phosphorus-nitrogen compounds. Part 36. Syntheses, Langmuir-Blodgett thin films and biological activities of spiro-bino-spiro trimeric phosphazenes(Royal Soc Chemistry, 2016) Asmafiliz, Nuran; Kilic, Zeynel; Civan, Mehmet; Avci, Orhan; Gonder, L. Yasemin; Acik, Leyla; Hokelek, TuncerThe condensation reactions of hexachlorocyclotriphosphazene (N3P3Cl6, trimer) with the symmetric N2N2 or N2O2 donor type tetradentate bulky ligands (1-4) gave partly substituted spiro-bino-spiro (sbs) (5-8) trimeric phosphazenes. Compounds 5-8 reacted with pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD) to give octapyrrolidino-(9-12), morpholino-(13-16) and DASD-substituted cyclotriphosphazenes (17-20). The structures of the phosphazenes have been elucidated using FTIR, MS, H-1, C-13{H-1} and P-31{H-1} NMR, and HSQC spectral data. The molecular and solid-state structures of 5, 6 and 12 were verified by single crystal X-ray diffraction techniques. On the other hand, the ultrathin and highly ordered Langmuir-Blodgett (LB) films of compounds 6, 7, 9 and 12 were also fabricated. The structural characterization of the LB films was made using p-polarized grazing angle (GAIR) and horizontal attenuated total reflectance (HATR) techniques. All the novel phosphazene derivatives were evaluated for antibacterial activities against Gram-positive (G+) and Gram-negative (G-) bacteria and for antifungal activities against yeast strains. In addition, the cytotoxic effects of compounds 9, 13, 15, 16, 19 and 20 were investigated against L929 fibroblast and MDA-MB-231 breast cancer cells. The most active one among these compounds was compound 9 at 6.25 mu g mL(-1) concentration. The interactions between compounds 5-20 and pBR322 plasmid DNA were determined by agarose gel electrophoresis.Öğe Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm(Elsevier Science Sa, 2019) Asmafiliz, Nuran; Berberoglu, Ipek; Ozgur, Mehtap; Kilic, Zeynel; Kayalak, Hande; Acik, Leyla; Hokelek, TuncerIn the present study, the partly and fully-substituted monospiro (4-6, 4a-6d), cis-dispiro (7-9), trans-dispiro (10-15) cyclotriphosphazenes were synthesized for the investigations of their chemical, stereogenic and biological properties. The cis/trans phosphazenes (7-12) have two stereogenic P centers. They are expected to be in meso and racemic forms. In addition, the structures of four compounds were evaluated using X-ray crystal-lographic data. Compound 13 was found to be a single enantiomer (RR) in the solid state, as also proved with its CD spectrum. The antibacterial and antifungal activities of the phosphazenes were elucidated for against Gram-positive (G+) and Gram-negative (G-) bacteria, and yeast strains, respectively. Of the compounds, 14 exhibits strong antimicrobial activity against most of the tested organisms, especially B. cereus and E. hirae. MBC and MFC values of compounds on different bacterial and fungal species ranged from < 9.8 mu M to 2500 mu M. Furthermore, the cytotoxic activities of 6, 4c, 10 and 14 were investigated against L929 fibroblast and DLD-1 cells, and 14 was the most cytotoxic compound against DLD-1.Öğe 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)(Springer, 2022) Iscan, Ozlem; Cemaloglu, Resit; Asmafiliz, Nuran; Zeyrek, Celal Tugrul; Kilic, Zeynel; Acik, Leyla; Aydin, BetulMono-/dispirocyclotriphosphazenes with pendant arm(s) are robust, but they are less investigated inorganic ring systems. In this study, a series of mono (3 and 4)- and dispirocyclotriphosphazenes with 4-chloro-benzyl pendant arm(s) (13-16) was obtained from the Cl exchange reactions of hexachlorocyclotriphosphazene with sodium (N-benzyl)aminopropanoxides (1 and 2). When compound (3) reacted with excess pyrrolidine, morpholine, tetra-1,4-dioxa-8-azaspiro[4,5]decane (DASD) and piperidine, the fully substituted monospirocyclotriphosphazenes (7, 9, 10 and 12) occurred. But, the reactions of 4 with excess piperidine and morpholine produced the gem-piperidino (5)- and morpholino (6)-substituted monospirocyclotriphosphazenes, whereas the reactions of 4 with excess pyrrolidine and DASD gave the fully substituted monospirocyclotriphosphazenes (8) and (11). However, it should be indicated that these derivatives were obtained to be used for the investigation of their spectral, stereogenic and biological properties. The structures of 5, 7 and 14 were determined crystallographically. X-ray data of 5 and 14 displayed that both of compounds were chiral in solid state, and their absolute configurations were assigned as R and RR. Additionally, the antimicrobial activities of phosphazenes were investigated. Minimum inhibitory concentrations, minimal bacterial concentrations and minimum fungicidal concentrations of phosphazenes were determined. The interactions of phosphazenes with plasmid DNA were evaluated by agarose gel electrophoresis. The cytotoxic activities of compounds were studied against L929 fibroblast and DLD-1 colon cancer cells. In addition, density functional theory calculations of 5, 7 and 14 were reported, and their molecular docking studies with DNA, E. coli DNA gyrase and topoisomerase IV were presented.Öğe Phosphorus-nitrogen compounds: part 57-Syntheses of tetrachloro- and tetraaminobenzylspiro(N/N) cyclotriphosphazenes: chemical, structural characterizations, bioactivity and molecular docking studies(Springer, 2022) Berberoglu, Ipek; Cemaloglu, Resit; Asmafiliz, Nuran; Kilic, Zeynel; Zeyrek, Celal Tugrul; Acik, Leyla; Koyunoglu, DilaDespite a significant amount of research in the field of cyclotriphosphazene chemistry, bioactivity and molecular docking studies of this class of cyclotriphosphazenes have still not been adequately studied. In this study, for bioactivity studies, tetrachlorobenzylmonospiro(N/N)cyclotriphosphazenes (4, 5 and 6) were synthesized by the reactions of hexachlorocyclotriphosphazene (N3P3Cl6; trimer; HCCP) with diamines (1, 2 and 3), respectively. Reactions of 4, 5 and 6 with excess pyrrolidine, piperidine, morpholine and 1, 4-dioxa-8-azaspiro[4.5]decane (DASD) gave the tetrapyrrolidino (7, 8 and 9), tetrapiperidino (10, 11 and 12), tetramorpholino (13, 14 and 15) and tetraDASD (16, 17 and 18) substituted benzylmonospiro(N/N) cyclotriphosphazenes. Microanalytical, spectral and crystallographic data (for 6 and 15) revealed the structures of the cyclotriphosphazenes. Antibacterial and antifungal activities of all phosphazenes against selected strains of bacteria and yeast, and pBR322 plasmid DNA cleavage activities were discussed. MIC values of 11 and 12 (78.1 and 156.3 mu M, respectively) against C. albicans are higher than the reference antibiotic Ketoconazole. Cytotoxic activities of five phosphazenes against L929 Fibroblast and DLD-1 cells were evaluated. Additionally, Density Functional Theory (DFT) calculations of 6 and 15 were performed. Molecular docking studies of 6 and 15 with DNA, endonuclease BamHI, S. aureus Dihydrofolate Reductase and E. coli DNA gyrase were presented. [GRAPHICS] .Öğe Phosphorus-nitrogen compounds: part 57—Syntheses of tetrachloro- and tetraaminobenzylspiro(N/N)cyclotriphosphazenes: chemical, structural characterizations, bioactivity and molecular docking studies(Springer Science and Business Media B.V., 2022) Berberoğlu, İpek; Cemaloğlu, Reşit; Asmafiliz, Nuran; Kılıç, Zeynel; Zeyrek, Celal Tuğrul; Açık, Leyla; Koyunoğlu, DilaAbstract: Despite a significant amount of research in the field of cyclotriphosphazene chemistry, bioactivity and molecular docking studies of this class of cyclotriphosphazenes have still not been adequately studied. In this study, for bioactivity studies, tetrachlorobenzylmonospiro(N/N)cyclotriphosphazenes (4, 5 and 6) were synthesized by the reactions of hexachlorocyclotriphosphazene (N3P3Cl6; trimer; HCCP) with diamines (1, 2 and 3), respectively. Reactions of 4, 5 and 6 with excess pyrrolidine, piperidine, morpholine and 1, 4-dioxa-8-azaspiro[4.5]decane (DASD) gave the tetrapyrrolidino (7, 8 and 9), tetrapiperidino (10, 11 and 12), tetramorpholino (13, 14 and 15) and tetraDASD (16, 17 and 18) substituted benzylmonospiro(N/N)cyclotriphosphazenes. Microanalytical, spectral and crystallographic data (for 6 and 15) revealed the structures of the cyclotriphosphazenes. Antibacterial and antifungal activities of all phosphazenes against selected strains of bacteria and yeast, and pBR322 plasmid DNA cleavage activities were discussed. MIC values of 11 and 12 (78.1 and 156.3 µM, respectively) against C. albicans are higher than the reference antibiotic Ketoconazole. Cytotoxic activities of five phosphazenes against L929 Fibroblast and DLD-1 cells were evaluated. Additionally, Density Functional Theory (DFT) calculations of 6 and 15 were performed. Molecular docking studies of 6 and 15 with DNA, endonuclease BamHI, S. aureus Dihydrofolate Reductase and E. coli DNA gyrase were presented. Graphical abstract: [Figure not available: see fulltext.] © 2022, The Author(s), under exclusive licence to Springer Nature B.V.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 AytunaOrganic-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%.Öğe 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)(Springer Science and Business Media Deutschland GmbH, 2022) İşcan, Özlem; Cemaloğlu, Reşit; Asmafiliz, Nuran; Zeyrek, Celal Tuğrul; Kılıç, Zeynel; Açık, Leyla; Aydın, BetülMono-/dispirocyclotriphosphazenes with pendant arm(s) are robust, but they are less investigated inorganic ring systems. In this study, a series of mono (3 and 4)- and dispirocyclotriphosphazenes with 4-chloro-benzyl pendant arm(s) (13–16) was obtained from the Cl exchange reactions of hexachlorocyclotriphosphazene with sodium (N-benzyl)aminopropanoxides (1 and 2). When compound (3) reacted with excess pyrrolidine, morpholine, tetra-1,4-dioxa-8-azaspiro[4,5]decane (DASD) and piperidine, the fully substituted monospirocyclotriphosphazenes (7, 9, 10 and 12) occurred. But, the reactions of 4 with excess piperidine and morpholine produced the gem-piperidino (5)- and morpholino (6)-substituted monospirocyclotriphosphazenes, whereas the reactions of 4 with excess pyrrolidine and DASD gave the fully substituted monospirocyclotriphosphazenes (8) and (11). However, it should be indicated that these derivatives were obtained to be used for the investigation of their spectral, stereogenic and biological properties. The structures of 5, 7 and 14 were determined crystallographically. X-ray data of 5 and 14 displayed that both of compounds were chiral in solid state, and their absolute configurations were assigned as R and RR. Additionally, the antimicrobial activities of phosphazenes were investigated. Minimum inhibitory concentrations, minimal bacterial concentrations and minimum fungicidal concentrations of phosphazenes were determined. The interactions of phosphazenes with plasmid DNA were evaluated by agarose gel electrophoresis. The cytotoxic activities of compounds were studied against L929 fibroblast and DLD-1 colon cancer cells. In addition, density functional theory calculations of 5, 7 and 14 were reported, and their molecular docking studies with DNA, E. coli DNA gyrase and topoisomerase IV were presented. Graphic abstract: [Figure not available: see fulltext.] © 2021, The Author(s), under exclusive licence to Springer Nature Switzerland AG.Öğe Syntheses, spectroscopic and crystallographic characterizations of cis- and trans-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activities(Royal Soc Chemistry, 2018) Tumer, Yasemin; Asmafiliz, Nuran; Zeyrek, C. Tugrul; Kilic, Zeynel; Acik, Leyla; Celik, S. Pinar; Hokelek, TuncerNew cis-(4-6) and trans-dispirocyclic ferrocenylphosphazene derivatives (7-9) were obtained by reactions of hexachlorocyclotriphosphazene (N3P3Cl6) with N-alkyl-N-monoferrocenyldiamines of the formula FcCH(2)NH(CH2)(n)NHR [n = 2, R = CH3 (1); n = 2, R = C2H5 (2) and n = 3, R = CH3 (3)]. Characterizations of the products were performed using MS, FTIR, H-1, C-13 and P-31 NMR techniques. The crystal structures of 5 (with 8), 6, 7 and 9 were determined by X-ray crystallography. The most important result of this study was that the trans chiral phosphazenes crystallized as only one enantiomer. Studies of the antibacterial and antifungal activity of the phosphazenes (4-9) showed that compounds 6 and 7 were effective against P. vulgaris and K. pneumoniae. The cytotoxic activities of 4-9 against L929 fibroblasts and DLD-1 colon cancer cells were investigated. The necrotic effects of 4 and 7 were greater in the DLD-1 cell line than those in the L929 cell line. DFT calculations were carried out using the B3LYP functional with the LANL2DZ basis set to determine the energies, the orientations of the molecular orbitals (HOMOs and LUMOs) and the molecular electrostatic potential (MEP) surfaces of the partly substituted cyclotriphos-phazenes (6, 7 and 9). The results for 6, 7 and 9 revealed that these bonded to the active sites of A-DNA and B-DNA by weak non-covalent interactions, which was also supported by molecular docking investigations.
