The reactions of hexachlorocyclotriphosphazene with piperidine, N-(1-naphthyl)ethylenediamine and 2-(2-hydroxyethylamino)ethanol. Antimicrobial activities of iminodiethoxy-substituted cyclotriphosphazene derivatives

Abstract

A series of cyclotriphosphazene derivatives (5–16) were synthesized from the reactions of hexachlorocyclotriphosphazene (1, N3P3Cl6) with piperidine (2), N-(1-naphthyl)ethylenediamine (3) and 2-(2-hydroxyethylamino)ethanol (4). Of the synthesized compounds, 2-piperidino-2,4,4,6,6-pentachlorocyclotri phosphazatriene, N3P3Cl5[N-(C5H10)] (5); 2,4-piperidino-2,4,6,6-tetrachlorocyclo triphosphazatriene, N3P3Cl4[N-(C5H10)]2 (6); 2,4,6-piperidino-2,4,6-trichlorocyclo triphosphazatriene, N3P3Cl3[N-(C5H10)]3 (7); 2,2,4,6-piperidino-4,6-dichlorocyclotri phosphazatriene, N3P3Cl2[N-(C5H10)]4 (8); the 2,4,6,6-tetrachloro-2,4-non-gem-N-(1-naphthyl)ethylendiamino)-cyclotri phosphazatriene, N3P3Cl4[NH–(CH2)2–NH–(C10H7)]2 (9); and the 2,2,4,4,6,6-trispiro-2,2′-iminodiethoxy-cyclotriphosphazatriene, N3P3[O–(CH2)2–NH–(CH2)2O]3 (14) derivatives are reported for the first time, others (10–13, 15 and 16) were previously reported. The derived compounds (5–16) were structurally elucidated by elemental analysis and spectral data of 1H and 31P NMR and TLC-MS. Water-soluble hexachlorocyclotriphosphazene derivatives (10–16) were screened for their antimicrobial activities against three human pathogens; Escherichia coli W3110, Staphylococcus aureus ATCC 25923, and Candida albicans ATCC 10231 and compounds 10, 12, and 16 found to exhibit significant antimicrobial activities against the indicated microorganism.