Synthesis and cytostatic activity of purine nucleosides derivatives of allofuranose

Several new purine nucleosides derivatives of allofuranose were prepared according to Vorbrüggen method, starting from 1,2,5,6-di-O-isopropylidene-α-d-allofuranose and using 1,2,3,5,6-pentaacetoxy-β-d-allofuranose as key intermediate. The synthesized allofuranosyl nucleosides, as well as some acetyl derivatives, were evaluated for their cytotoxicity in vitro in three human cancer cell lines (MCF-7, Hela-229 and HL-60). Among the studied compounds the 9-(2,3,5,6-tetra-O-acetyl-β-d-allofuranosyl)-2,6-dichloropurine (9) was the most potent one on the three cell lines evaluated, being its activity against HL-60 cells similar to cisplatin.

Graphical abstractSeveral new purine nucleosides derivatives of allofuranose were synthesized and evaluated for their cytotoxicity in vitro in three human cancer cell lines. Among the studied compounds, the acetyl derivative 9 was the most potent one on the three cell lines evaluated.Figure optionsDownload full-size imageDownload as PowerPoint slide