Novel 1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino
reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was
optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate
in respect of the catalyst, the base and the solvent, as well as of the reaction parameters
(molar ratio of the starting materials, atmosphere, temperature and reaction time).
The method elaborated could be applied to a range of organic azides and dialkyl phosphites,
which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity
on different cell lines and the antibacterial activity of the synthesized 1,2,3-triazol-5-yl-phosphonates
was explored. According to the IC50 values determined, only modest antibacterial effect
was detected, while some derivatives showed moderate activity against human promyelocytic
leukemia HL-60 cells.
