The investigations of synthesis and biological activities of 2-thiophenylmethyl(N/N)spirocyclotriphosphazene derivatives

In this study, Schiff bases were obtained by reacting 2-thiophenecarboxaldehyde with N-methyl-1,2-diaminoethane and N-ethyl-1,2-diaminoethane in ethanol, and diamine ligands (1 and 2) were obtained from the reduction of these Schiff bases with NaBH4. Regioselectively, tetrachloro-2-thiophenylmethylspiro(N/N)cyclotriphosphazenes (3 and 4) were obtained by the reaction of these ligands with hexachlorocyclotriphosphazatriene, N3P3Cl6 (HCCP, trimer). Substituted (5-10 and 15-18) cyclotriphosphazenes were obta-ined from the reactions of tetrachloro-2-thiophenylmethylspiro(N/N)cyclotriphosphaze-nes (3 and 4) with primary (n-propylamine and iso-propylamine), secondary amines (pyrrolidine and morpholine), 4-hydroxy-6-methyl-2H-pyran-2-on and 4-hydroxy-coumarin. In addition, partially substituted morpholine (11 and 12), propylamine (13) and isopropylamine (14) 2-thiophenylmethylspiro(N/N)cyclotri-phosphazene compounds were obtained. Compounds were separated by column chromatography method and purified by crystallization. The structures of the synthesized phosphazenes were elucidated by elemental analysis, mass (ESI-MS), FTIR, one dimention (1H, 13C- and 31P-NMR; DEPT) and two dimention (HSQC and HMBC) spectroscopy techniques. The solid state structures of phosphazene derivatives, which can be obtained in suitable single crystals, were characterized by X-ray diffraction method and the conformations of phosphazene and spiro-rings were determined. The geometrical isomers, bond lengths, bond angles, torsion/dihedral angles and hydrogen bonds of the compounds were investigated. In addition, the interactions of the synthesized compounds with DNA, their antimicrobial and antioxidant activities were also evaluated.