Phosphorus-nitrogen compounds. Part 48. syntheses of the phosphazenium salts containing 2-pyridyl pendant arm: structural characterizations, thermal analysis, antimicrobial and cytotoxic activity studies

533-550The phosphazenium salts (protic ionic liquids, PILs/protic molten salts, PMOSs) (6a-6d and 7a) of the free phosphazene bases (4a-4d and 5a) have been prepared by the reactions of the corresponding cyclotriphosphazenes with the bulky gentisic acid. The structures of the PMOS have been evaluated using the elemental analyses, FTIR, 1H, 13C{1H} and 31P{1H} NMR data. The molecular and crystal structures of 4a and 6c are established by X-ray crystallography. The thermal properties of the PMOS are determined using TG and DTA techniques. On the other hand, the antimicrobial activities of the free phosphazene bases (4a-4d and 5a-5d) and PMOSs (6a-6d and 7a) are screened against the selected bacteria and yeast strains. The antimicrobial activities of the free phosphazene bases and the PMOSs are compared. The interactions of the phosphazenes and their salts with plasmid DNA are elucidated by the agarose gel electrophoresis. The evaluations of the cytotoxic activities of these compounds are also studied against to L929 fibroblast and breast cancer cells (MDA-MB-231)

Phosphorus-nitrogen compounds. Part 48. Syntheses of the phosphazenium salts containing 2-pyridyl pendant arm: Structural characterizations, thermal analysis, antimicrobial and cytotoxic activity studies

The phosphazenium salts (protic ionic liquids, PILs/protic molten salts, PMOSs) (6a-6d and 7a) of the free phosphazene bases (4a-4d and 5a) were prepared by the reactions of the corresponding cyclotriphosphazenes with the bulky gentisic acid. The structures of the PMOS were evaluated using the elemental analyses, FTIR, 1H, 13C{1H} and 31P{1H} NMR data. The molecular and crystal structures of 4a and 6c were established by X-ray crystallography. The thermal properties of the PMOS were determined using TG and DTA techniques. On the other hand, the antimicrobial activities of the free phosphazene bases (4a-4d and 5a-5d) and PMOSs (6a-6d and 7a) were screened against the selected bacteria and yeast strains. The antimicrobial activities of the free phosphazene bases and the PMOSs were compared. The interactions of the phosphazenes and their salts with plasmid DNA were elucidated by the agarose gel electrophoresis. The evaluations of the cytotoxic activities of these compounds were also studied against to L929 fibroblast and breast cancer cells (MDA-MB-231).  

The Spectroscopic and Thermal Properties, Antimicrobial Activities and DNA Interactions of 4-(Fluorobenzyl)Spiro(N/O) Cyclotriphosphazenium Salts

The protic ionic liquids (PILs) (3a-3d) were synthesized from the reactions of tetraamino-4-(fluorobenzyl)spiro(N/O)cyclotriphosphazenes (2a-2d) with the gentisic acid in THF. The structures of the PILs were verified by elemental analyses, Fourier transform infrared (FTIR), 1H, 13C {1H} and 31P {1H} NMR techniques. The thermal properties of the PILs were evaluated using TG/DTG/DTA instrument. On the other hand, the antimicrobial activities of the PILs were examined against some bacteria and fungi, and the obtained results were compared with the evaluations of the corresponding fully substituted cyclotriphosphazene bases. The interactions between the PILs and supercoiled PBR322 DNA were also scrutinized, and it was determined that they exhibited significant conformational changes

Phosphorus-nitrogen compounds. Part 37. Syntheses and structural characterizations, biological activities of mono and bis(4-fluorobenzyl)spirocyclotetraphosphazenes

Hokelek, Tuncer/0000-0002-8602-4382; okumus, aytug/0000-0002-2169-5695WOS: 000404350900068The Cl substitution reactions of octachlorocyclotetraphosphazene, N4P4Cl8, with one equimolar amount of (4-fluorobenzyl)diamines (1-3) affords mono(4-fluorobenzyl) spirocyclotetraphosphazenes (4-6) as minor products. However, the reactions of N4P4Cl8 with two equimolar amounts of (4-fluorobenzyl) diamines (1-3) leads to the formation of mono (4-6), 2-trans-6-bis (7-9, as major products) and 2-cis-6-bis (4-fluorobenzyl) spirocyclotetraphosphazenes (10-12). The 2-cis-6-bis compounds (10 and 12) were separated and purified using column chromatography as minor products, whereas compound 11 could not be isolated. The mono-spiro (4-6) and 2-trans-6-bis-spiro (7-9) cyclotetraphosphazenes were reacted with excess pyrrolidine in THF to afford the fully substituted hexapyrrolidino (4a-6a) and tetra-pyrrolidino (7a-9a) products in high yield. Compound 9 was also reacted with piperidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD) to obtain the tetraamino products (9b, 9c and 9d), respectively, due to its very high yield. The elemental analyses, mass spectra (ESI-MS), Fourier transform infrared (FTIR) spectra, and H-1, C-13{H-1}, and P-31{H-1} NMR data of the cyclotetraphosphazenes were in agreement with the suggested structures. The molecular structures of 7, 9 and 12 were established by X-ray crystallography. The antibacterial activities of the compounds against G(+) and G(-) bacteria and their antifungal activities against yeast strains were scrutinized. The results indicated that 4a and 5a were the most active compounds, especially to yeast strains. In addition, it was found that the most active compound toward DNA was 8. The cytotoxic activities of the cyclotetraphosphazenes against L929 fibroblast and MCF-7 breast cancer cell lines were elucidated. Compound 8a exhibited the most toxic effects against both types of cells.Turkish Academy of Sciences (TUBA)Turkish Academy of SciencesThe author Z. K. thanks the Turkish Academy of Sciences (TUBA) for partial support of this study