The Syntheses and Structural Characterizations, Antimicrobial Activity and in Vitro Dna Binding of 4-Fluorobenzylspiro(n/O)cyclotriphosphazenes and Their Phosphazenium Salts

Abstract

Abstract:In the present study, the condensation reaction of N3P3Cl6 (1) with sodium 3-(4-fluorobenzylamino)-1-propanoxide gave partly substituted 4-fluorobenzylspirocyclotriphosphazene (2). The Cl replacement reactions of 2 with excess benzylamine, n-hexylamine, n-butylamine and n-propylamine led to the formation of the corresponding 4-fluorobenzylspiro(N/O)tetrabenzylamino (3a), tetrahexylamino (3b), tetrabutylamino (3c) and tetrapropylamino (3d) cyclotriphosphazenes. With the protic ionic liquids (PILs), phosphazenium salts (4a-4d), were obtained from the reactions of the corresponding phosphazene bases (3a-3d) with gentisic acid in dry THF. The structures of all the isolated cyclotriphosphazene derivatives were determined by elemental analyses, FTIR and H} NMR techniques. The crystal structure of 4d was verified by X-ray diffraction analysis. All the compounds were screened for antibacterial and antifungal activities against bacteria and yeast strains. The interactions of the compounds with supercoiled pUC18 plasmid DNA were investigated.

Phosphorus-nitrogen compounds (Part 51): the relationship betweenspectroscopic and crystallographic data of mono- and di-spirocyclophosphazenederivatives with 4-fluoro/nitrophenylmethyl pendant arm/arms

“…However, N 2 atoms in partly substituted phosphazenes decreased due to electron-withdrawing power of the Clatoms. Nevertheless, protonation of type I heterocyclic amine substituted free cyclotriphosphazene bases with bulky organic acids (gentisic and γ -resorcylic acids) took place on the N2-atom [49] (type V) instead of N1atom [54,55] of the 4-fluorobenzylspirocyclotriphosphazenes. The H + ion may be exchanged between the N1and N2-atoms of the cyclotriphosphazene ring in the solution at ambient temperature.…”

“…In the last decade, 4-fluorobenzyl pendant armed monospiro and dispiro phosphazenes were prepared from the separate reactions of N 3 P 3 Cl 6 and N 4 P 4 Cl 8 with 4-fluorobenzyl-NN/NO donor type ligands [47][48][49][50][51][52]. The phosphezenium salts (protic ionic liquids, PILs or protic molten salts, PMOSs) of fully substituted 4-fluorobenzyl spirocyclotriphosphazenes were also synthesized via reactions of free phosphazene bases with bulky organic acids [53][54][55]. The spectroscopic and stereogenic properties, and biological activity (antibacterial, antifungal, and cytotoxic activities) of all the (4-fluorobenzyl)spirocyclophosphazenes and some of their phosphazenium salts have been investigated by our research groups [47][48][49][50][51][52][53][54][55].…”

Phosphazene-Based Ionic Liquids

“…PzILs are prepared by quaternization of a wide variety of phosphazenes either at the sidegroup or at the skeletal nitrogen atoms. These ILs have been used as anticancer, antibacterial reagents [31][32][33][34], adsorbents and surface modifiers of fluorescent nanoparticles [35], lubricants [36,37], chemosensors for metal ions [38], electrolyte solutions for energy storage devices [39][40][41], as gate dielectric layer for OFETs [42], or as polyelectrolytes [26,43,44].…”

“…Recently, aminocyclotriphosphazenes have received greater attention due to their anti-cancer agent properties [45,46]. In contrast to cyclotriphosphazene derivatives, there are not many studies related to cyclotriphosphazene salts as antimicrobial and anticancer agents [31][32][33][34]. Phosphazenium salts are very soluble in common apolar and polar organic solvents and some are quite soluble in water.…”

The reactions of N$_{3}$P$_{3}$Cl$_{6}$ with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes

“…19 The starting spiro phosphazene derivative, 4-fluorobenzyl(N/O)spirocyclotriphosphazene (2), was also prepared according to the literature. 19 The reactions of 2 with excess monoamines gave the fully substituted cyclotriphosphazenes (2a-2d). The estimated yields of these compounds are in the range of 61%-80%.…”