Phosphorus–nitrogen compounds. Part 35. Syntheses, spectroscopic and electrochemical properties, and antituberculosis, antimicrobial and cytotoxic activities of mono-ferrocenyl-spirocyclotetraphosphazenes. (9th May 2016) - Okumuş, Aytuğ
Abstract : The syntheses, in vitro antituberculosis and cytotoxic activities of cyclotetraphosphazenes were investigated. Abstract : The reactions of octachlorocyclotetraphosphazene, N4 P4 Cl8, with N -alkyl- N -mono-ferrocenyldiamines, FcCH2 NH(CH2 ) n NHR 1 [ n = 2, Fc = ferrocene, R 1 = Me (1 ); n = 2, R 1 = Et (2 ) and n = 3, R 1 = Me (3 )], led to the formation of monoferrocenyl-spirocyclotetraphosphazenes (4–6 ). When the reactions were carried out with excess pyrrolidine, morpholine and 1, 4-dioxa-8-azaspiro[4, 5]decane (DASD), the fully substituted products (4a–6c ) were obtained in high yields. The structures of all the phosphazene derivatives were characterized by MS, FTIR, 1 H, 13 C and 31 P NMR, HSQC and HMBC techniques. The crystal structures of4a and5a were determined by X-ray crystallography. The electrochemically reversible one-electron oxidation of Fc redox centers was observed for cyclotetraphosphazenes. The fully substituted phosphazenes (4a–6c ) were evaluated for their antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv, and compounds4a–6a and5c were found to be active. The antibacterial activities of phosphazenes4a–6c against G(+) and G(−) bacteria and their antifungal activities against yeast strains were carefully scrutinized. The results indicate that compounds4a–6a, 6b, 4c and5c are very effective against yeast strains. The anticandidal activities of6a and6b make them promising anticandidal agents. The interactions of these compounds with plasmid DNA and their cytotoxic activity against L929 fibroblast and DLD-1 colon cancer cell lines were also investigated.