Synthesis, characterization, and biological evaluation of new oxime-phosphazenes

Abstract

Hexachlorocylotriphosphazene (1) was reacted with 4-hydroxy-3-methoxybenzaldehyde to give hexakis[(4-formyl-2-methoxy)phenoxy]cyclotriphosphazene (2). Hexakis[(4-(hydroxyimino)2-methoxy)phenoxy]cyclotriphosphazene (3) was synthesized by reaction of 2 with hydroxlamine hydrochloride in pyridine. Compound 3 was reacted with benzyl chloride, acetyl chloride, allyl bromide, benzoyl chloride, propanoyl chloride, 4-methoxybenzoyl chloride, 2-chlorobenzoyl chloride, chloroacetyl chloride, methyl iodide, and thiophene-2-carbonyl chloride. From these reactions, full or partially substituted compounds were obtained, usually in high yields. Pure or defined products could not be obtained from reaction of 3 with methacryloyl chloride and O-acetylsalicyloyl chloride. The structures of the compounds were determined by elemental analysis, and IR, 1 H, 13 C, and 31 P NMR spectroscopy. The synthesized compounds were screened for in-vitro antimicrobial activity against two Gram-positive bacteria (Staphylococcus aureus and Enterococcus faecalis), two gram-negative bacteria (Escherichia coli and Klebsiella pneumonia), and fungal strains (Aspergillus niger, and Candida albicans) by the agar well diffusion method. Few compounds had significant activity against both Grampositive and Gram-negative bacteria. None of the compounds had antifungal activity except compounds 7 and 9, which had moderate activity.

Synthesis, structural characterization and anti-carcinogenic activity of new cyclotriphosphazenes containing dioxybiphenyl and chalcone groups

“…The chalcone-phosphazene compounds were generally obtained in high yields. These compounds were characterized by elemental analysis, FT-IR, 1 H, 13 …”

“…Microanalysis was carried out by a LECO 932 CHNS-O apparatus. 1D ( 1 H, 13 C, 13 C APT and 31 P NMR) spectra were recorded using a Bruker DPX-400 spectrometer. The 1 H, 13 C and 31 P NMR chemical shifts were measured using TMS as an internal standard, whereas those for 31 P were measured using 85% H 3 PO 4 as an external standard.…”

“…The phosphazene derivatives have various physical and biological properties, for example liquid crystals [2,3], electrical conductivity [4], flame retardants [5][6][7], electrolytes for rechargeable batteries [8], fire resistant materials [9], dielectric properties [10], biomedical applications [11,12], antimicrobial, antibacterial [13][14][15][16][17][18], anti-leukemic [19] and strong anti-tumor activity [20][21][22][23][24][25][26][27].…”

“…The synthesis of different phosphazene compounds has been reported [13,[45][46][47][48][49][50][51][52][53] but there are only four articles about synthesis of the phosphazene compounds bearing chalcone groups [10,[54][55][56], there are, however, no studies about synthesis of dioxybiphenyl substituted chalcone-cyclophosphazene compounds. The cyclotriphosphazenes bearing 2,2 0 -dihydroxybiphenyl are much more stable to hydrolysis and thermal decomposition than hexachlorocyclotriphosphazene [1].…”

Phosphorus–nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes

“…Recently, our group observed that the phosphazenes bearing vanillinato and pendant ferrocenyl groups were active against E. coli, S. aureus, B. cereus and B. subtilis, indicating that the antimicrobial activity of the ferrocenyl cyclotriphosphazenes vary depending on the substituents (pyrrolidino, morpholino and vanillinato groups) bonded to the P-atoms [14]. Besides, some phenoxy phosphazenes containing oxime and/or Schiff base groups were effective against E. coli and S. aureus [49,50].…”