Synthesis and cytostatic activity of purine nucleosides derivatives of allofuranose.

摘要

Several new purine nucleosides derivatives of allofuranose were prepared according to Vorbruggen method, starting from 1,2,5,6-di-O-isopropylidene-alpha-D-allofuranose and using 1,2,3,5,6-pentaacetoxy-beta-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-beta-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.