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

Year 2016, Volume: 3 Issue: 3, 25 - 46, 08.01.2017

Gamze Elmas , Aytuğ Okumuş , Zeynel Kılıç , L. Yasemin Gönder Leyla Açık , Tuncer Hökelek

https://doi.org/10.18596/jotcsa.04055

Cited By: 13

Abstract

In the present study, the condensation reaction of N₃P₃Cl₆ (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 ¹H, ¹³C{¹H}, ³¹P{¹H} 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.

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