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    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, Dila
    Abstract: 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.
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    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, Betül
    Mono-/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.