Fatih Aslan

Antimicrobial and biological effects of N-diphenylphosphoryl-P-triphenylmonophosphazene-II and di(o-tolyl)-phosphoryl-P-tri(o-tolyl)monophosphazene-III on bacterial and yeast cells

The purpose of the study was to synthesize and evaluate the antimicrobial effects of two monophosphazenes, N-diphenylphosphoryl-P-triphenylmonophosphazene-II and N-di(o-tolyl)phosphoryl-P-tri(o-tolyl)monophosphazene-III on bacterial and yeast strains. The biological effects of these molecules were compared with a potential antioxidant vitamin E. According to results, the triphenyl monophosphazene-II has antimicrobial effect on all the bacterial and yeast cells, but tri(o-tolyl)monophosphazene-III has only antimicrobial effect on some bacterial cells. When the concentration of triphenyl monophosphazene-II was raised, it was observed that inhibition zone increased on the bacterial growth media. The biological effects of these molecules were compared to vitamin E in the Saccharomyces cerevisiae culture media. In 200 microg administered culture media, the cell density decreased in vitamin E, triphenyl monophosphazene-II and tri(o-tolyl)monophosphazene-III groups at the end of 24 and 48 h incubation times (p<0.001,p<0.05). While the cell densities in vitamin E and tri(o-tolyl)monophosphazene-II groups decreased partly at the end of 72 h incubation time (p<0.05), its level in triphenyl monophosphazene-II group increased (p<0.01) at the same incubation time. In 1,000 microg administered culture media, cell density was not found to differ between vitamin E and control groups at the end of 24h incubation time, but it was found that the cell densities in triphenyl monophosphazene and tri(o-tolyl)monophosphazene-III groups decreased at the same incubation time (p<0.001). The cell densities in tri(o-tolyl)monophosphazene-III group and triphenyl monophosphazene-II decreased at the end of 48 h incubation time (respectively, p<0.05,p<0.001). In 200 microg administered cell pellets, while the lipid level was not found to differ between control and vitamin E, the lipid level decreased in triphenyl monophosphazene-II and tri(o-tolyl)monophospazene-III groups (respectively, p<0.001,p<0.01). In 1,000 microg administered cell pellets, it was found that the lipid level decreased in vitamin E, triphenyl monophosphazene-II and tri(o-tolyl)monophosphazene-III groups (p<0.001,p<0.01).

The Synthesis and Characterization of Cycloalkoxy-Linear Phosphazenes

The reactions of N -dichlorophosphoryl- P -trichlorophosphazene, Cl 3 P=N--P(O)Cl 2 with the sodium salts of cyclopentanol, cyclohexanol, 4-methylcyclohexanol, 3-methylcyclohexanol, 3-methylcyclopentanol are discussed. Pentacycloalkoxy-substituted phosphazenes were obtained from cyclopentanol, 4-methylcyclohexanol, 3-methylcyclohexanol, 3-methylcyclopentanol. Tetrasubstituted derivative also was obtained from cyclohexanol at the same conditions. The structure of products was defined by IR, 1 H, 13 C, 31 P NMR, and mass spectroscopy.

The Synthesis and Characterization of Aryloxy-Linear Phosphazenes

The reactions of N-dichlorophosphoryl-P-trichloromonophosphazene with sodium o-methylphenoxide, sodium p-methylphenoxide, sodium f -naphthalenoxide, monosodium 4-(2-pyridylazo)resorcinol, and sodium 1-nitroso-2-naphthaleneoxide have been investigated. Experimental studies were carried out in argon atmosphere. The sodium aryloxides were prepared from naphthalene or phenol derivatives and metallic sodium. The phosphazene and phenolate or naphthaleneoxide were reacted at 0°;C and then refluxed. After the reaction products were separated by using column chromatography, the structures of the compounds were defined by elemental analysis, IR, 1 H, 13 C, 31 P NMR, and mass spectroscopy. Tetra- and pentasubstituted monophosphazenes were obtained from sodium o-methylphenoxide. Pentasubstituted derivatives also were obtained from sodium p-methylphenoxide and sodium f -naphthaleneoxide. Phosphazene or any phosphorus compound could not be isolated from the reaction of phosphazene with monosodium 4-(2-pyridylazo)resorcinol and sodium 1-nitroso-2-naphthaleneoxide.

The Synthesis of Hexaphenylcyclotriphosphazene in Improved Yield

The reaction between phenylmagnesium bromide and hexachlorocyclotriphophazene (N 3 P 3 Cl 6 ) ( 1 ) was reinvestigated for the synthesis of hexaphenylcyclotriphosphazene (N 3 P 3 Ph 6 ) ( 2 ) in high yield. The reaction is complete within two weeks at room temperature using toluene as solvent. When the reactants (PhMgBr and N 3 P 3 Cl 6 ) were employed in a 6:1, 36:1 and 72:1 molar ratio, compound 2 was obtained in 2.6%, 14%, and 33.4% yield, respectively. The formation of N 3 P 3 Cl 6 ( 2 ) during the reaction was followed by thin-layer chromatography. Compound 2 was characterized by elemental analysis, IR, UV-VIS, 1 H, 13 C, and 31 P NMR spectroscopy as well as by mass spectrometry.

Synthesis, Characterization, and Spectroscopic Properties of Hexa(4-Bromo-2-Formyl-Phenoxy)Cyclotriphosphazene and Hexa(4-Chloro-2-Formyl-Phenoxy)Cyclotriphosphazene and Fully Substituted Cyclotriphosphazene Derivatives Bearing a Schiff Base at Room Temperature

Abstract Hexa(4-bromo-2-formyl-phenoxy)cyclotriphosphazene (2) and hexa(4-chloro-2- formyl-phenoxy)cyclotriphosphazene (3) were obtained from the reactions of hexachloro- cyclotriphosphazene (1) with 5-bromosalicylaldehyde and 5-chlorosalicylaldehyde in the presence of (C2H5)3N and K2CO3 at room temperature, respectively. The new two organocyclotriphosphazenes bearing formyl groups were reacted with 4-cyano aniline, 2-phenyl aniline, 4-aceto aniline, 5-chloro-2-hydroxy aniline, 2-hydroxy aniline, 4-hydroxy aniline, 2-(4-morpholino)ethyl amine, 4-carboxy aniline, 4-carbomoyl aniline, 2-mercapto aniline, and 5-amino isoquonoline to prepare cyclotriphosphazene derivatives containing a Schiff base at room temperature. However, fully phenoxy-substituted cyclotriphosphazenes containing a Schiff base were isolated from the reactions of the compound 2 and 3 with 5-chloro-2-hydroxy aniline, 2-hydroxy aniline, 4-hydroxy aniline, and 2-(4-morpholino)ethyl amine. The structures of the synthesized compounds were characterized by elemental analysis, IR, and NMR (1H, 13C, 31P) spectroscopy. According to the results of the analysis, all synthesized compounds were found to be fully substituted organocyclotriphosphazenes, such as hexa[4-bromo-2-(5-chloro-2-hydroxy-pheyliminomethyl)phenoxy]cyclotriphosphaze (2a). All cyclotriphosphazene derivatives synthesized gave fluorescence emission peaks in range between 300 nm and 410 nm. GRAPHICAL ABSTRACT