THE SYNTHESES AND STRUCTURAL CHARACTERIZATIONS, ANTIMICROBIAL ACTIVITY AND IN VITRO DNA BINDING OF 4-FLUOROBENZYLSPIRO(N/O)CYCLOTRIPHOSPHAZENES AND THEIR PHOSPHAZENIUM SALTS

Abstract

In the present study, the condensation reaction of N 3 P 3 Cl 6 ( 1 ) with sodium 3-(4-fluorobenzylamino)-1-propanoxide gave partly substituted 4-fluorobenzylspiro cyclotriphosphazene ( 2 ). The Cl replacement reactions of 2 with excess benzylamine, n-hexylamine, n-buthylamine and n-propylamine led to the formation of the corresponding 4-fluorobenzylspiro(N/O)tetrabenzylamino ( 3a ), tetrahexylamino ( 3b ), tetrabuthylamino ( 3c ) and tetrapropylamino ( 3d ) cyclotriphosphazenes. 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 1 H, 13 C{ 1 H}, 31 P{ 1 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.