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

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)(2)O](3)(14) derivatives are reported for the first time, others (10-13,15and16) were previously reported. The derived compounds (5-16) were structurally elucidated by elemental analysis and spectral data of(1)H and(31)P NMR and TLC-MS. Water-soluble hexachlorocyclotriphosphazene derivatives (10-16) were screened for their antimicrobial activities against three human pathogens;Escherichia coliW3110,Staphylococcus aureusATCC 25923, andCandida albicansATCC 10231 and compounds10,12, and16found to exhibit significant antimicrobial activities against the indicated microorganism.