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.

Graphical abstractA 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.Figure optionsDownload full-size imageDownload as PowerPoint slide