Synthesis, spectral characterization and biological evaluation of phosphorylated derivatives of galanthamine

A series of novel phosphorylated derivatives of galanthamine 6–11 and 12–17 were synthesized in two step process with high yields. In the first step galanthamine 1 was reacted with bis (2-chloroethyl) phosphoramidic dichloride 2/4-nitrophenyl phosphorodichloridate 3 in presence of triethylamine (TEA) in dry tetrahydrofuran (THF) yielded the intermediates 4/5. They were further reacted with various compounds like 2-aminoethanol, ethyleneglycol, ethylenediamine, 2-aminoethanethiol, 2-hydroxyethanethiol, monopotassium dihydrogenphosphate to obtain the title compounds 6–11 and 12–17. The title compounds showed promising antimicrobial, antioxidant activities and was greatly influenced by the presence of different bioactive groups. A new series of phosphorylated derivatives of galanthamine 6–17 have been designed, synthesized and evaluated for antioxidant and antimicrobial properties. All the derivatives showed good antioxidant and antimicrobial activities, with compound 9 that has bis (2-chloroethyl) amino and 2-hydroxy ethanethiol moieties as substituents on the phosphorus atom reaching the best values for both assays. [Display omitted]