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Öğe 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; Hokelek, TuncerThe 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.Öğe Phosphorus-nitrogen compounds. part 38. Syntheses, characterizations, cytotoxic, antituberculosis and antimicrobial activities and DNA interactions of spirocyclotetraphosphazenes with bis-ferrocenyl pendant arms(Elsevier Science Sa, 2017) Elmas, Gamze; Okumus, Aytug; Cemaloglu, Resit; Kilic, Zeynel; Celik, Suheyla Pinar; Acik, Leyla; Hokelek, TuncerThe reactions of N4P4Cl8 (1), with two equimolar amounts of N-(1-ferrocenylmethyl)-N-methyl-propylenediamine gave the monoferrocenyl-spiro (as a byproduct), bisferrocenyl-2-trans-6-dispiro (2) and bisferrocenyl-2-cis-6-dispiro (3) cyclotetraphosphazenes. The 2-trans-6-dispiro (2) was reacted with excess monoamines to produce the tetraamino products (2a-2d). The one equimolar amount of the diamines and dialkoxides with 2 afforded the mono-diamino (2e and 2f) and mono-dialkoxy (2g and 2h) cyclotetraphosphazenes. Whereas, excess diamines and dialkoxides with 2 produced the bis-diamino (2i and 2j) and bis-dialkoxy (2k and 2l) bisferrocenyl-2-trans-6-dispirocyclotetraphosphazenes. The structures of the compounds were verified by elemental analyses, ESI-MS, FTIR, HSQC, HMBC, H-1, C-13, and P-31 NMR techniques. The molecular structures of 2 and 2b were established by X-ray crystallography. Compounds 2e and 2f have two stereogenic P-atoms. Additionally, the structures of 2i-2l containing tetraspiro rings in the skeletons look similar a propeller. The Fc groups of the cyclotetraphosphazenes were found to be redox active with two-reversible electron oxidations. The antimicrobial activity of the compounds was examined against some bacteria and yeast strains. The interactions of the compounds with DNA revealed that the compounds caused conformational changes even strand break on super-coiled DNA helix. Furthermore, the compounds (except 2, 2a and 2d) inhibited DNA restriction indicating compounds binding to A/A and G/G nucleotides of the DNA. The evaluations of the cytotoxic activity against L929 fibroblast and DLD-1 colon cancer cell lines were carried out. Some of the compounds were evaluated for antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv, and 2i and 2l displayed antituberculosis activity against H37Rv. (C) 2017 Elsevier B.V. All rights reserved.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 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%.
