Phosphazenes are open-chain {[Y(N=PX2)nX]; n=1,2,3…}, cyclic [(N=PX2)n (n=3, 4, 5...)] or polymeric {[X(PX2=N)nX]; X:Cl, n=15000} inorganic systems formed by sequential bonding of phosphorus and nitrogen atoms to each other. Especially cyclic phosphazenes [hexachlorocyclotriphosphazene (N3P3Cl6; trimer) and octachlorocyclotetraphosphazene (N4P4Cl8; tetramer)] have characteristic of simply functionalized with different substituents and gain different properties according to the linked substituents. Cyclic phosphazenes have an important role in biological activity studies in drug design, pharmacology and toxicology as well as determination of their chemical, physical, crystallographic and spectroscopic properties. In this study, the reaction between isophthalaldehyde and N-ethylethylenediamine resulted in a symmetrical benzyltetraamine ligand with a donor atom of N2N2 (1). Afterwards, according to the literature method, octachloro mono-spiro-bino-spiro(sbs) phosphazene derivative (2) was synthesized by the reaction of tetraamine ligand (1) with N3P3Cl6 in a stoichiometric ratio of 1:2. Fully and partially substituted mono-sbs-phosphazenes (3-4) were synthesized from the reaction of the compound 2 with n-propylamine and isopropylamine, respectively. In the case where the stoichiometric ratio of compound 2 and benzyltetraamine ligand 1 was 1:1, sbs-aba (5) and bis-sbs (6) phosphazene compounds were obtained. Structures of these phosphazenes enlightened with spectroscopic methods such as MS, 1H-NMR, 13C-NMR, 31P-NMR. The compounds were screened for antimicrobial and antifungal activity against G(+) and G(−) bacteria and fungi. MIC, MBC and MFC values of these cyclotriphosphazenes were also determined. In addition, the interactions of the synthesized phosphazenes with plasmid DNA were investigated by agarose gel electrophoresis.

Synthesis and biological activity studies of mono/bis(spiro-bino-spiro)cyclotriphosphazene derivatives

ACS Spring Meeting 2021

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