Journal
MOLECULES
Volume 25, Issue 11, Pages -Publisher
MDPI
DOI: 10.3390/molecules25112643
Keywords
1; 2; 3-triazoles; triazolyl phosphonates; copper(I) catalyst; domino reaction; multicomponent reaction; anticancer activity
Funding
- Hungarian Research Development and Innovation Office [FK123961]
- Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences [BO/00278/17/7, UNKP-19-3-I-BME-391]
- New National Excellence Program of the Ministry for Innovation and Technology
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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.
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