Synthesis and characterization of novel spiro-(2,2′-dioxybiphenyl)-cyclotriphosphazene derivatives bearing butylated oxyanisole groups and their antioxidant and antimicrobial activities

Synthesis of novel spiro-(2,2’-dioxybiphenyl)-cyclotriphosphazene derivatives bearing butylated oxyanisole groups and study of their antimicrobial and antioxidant properties. [Display omitted] In this study, novel cyclotriphosphazene derivatives, {[N3P3(biph)(BA)2] (6a/b), [N3P3(biph)(BA)3] (7), [N3P3(biph)2(BA)Cl (8) and [N3P3(biph)2(BA)2 (9)]}, (biph = 2′,2′′-dioxy-1′,1′′- biphenyl, BA = butylated oxyanisole}, were synthesized from the nucleophilic substitution reactions of butylated hydroxyanisole (BHA) (5) with [N3P3(biph)Cl4] (3) and [N3P3(biph)2Cl2] (4), respectively. The structures of all the products (6a/b, 7, 8 and 9) were determined -using elemental analysis, mass and (1H and 31P) NMR spectroscopic techniques. The molecular and crystal structure of compound 9 was also determined by single crystal X-ray crystallography. At the same time, the compounds (3, 4, 7, 8 and 9) were tested for their antimicrobial and antioxidant (free radical scavenging) activities. Of all, compounds 8 and 9 showed relatively significant antimicrobial activity against the control strains Bacillus cereus DSMZ 4312 (16,5 and 18,25 mm) and against Staphylococcus aureus ATCC 29213 (25 and 22,5 mm) compared to their positive controls. The MIC50 values of compounds 8 and 9 against Bacillus cereus were determined at 125 µg/mL and