α-Halogenated oxaphosphinanes: Synthesis, unexpected reactions and evaluation as inhibitors of cancer cell proliferation

• α-Halogenated (I, Br, Cl) oxaphosphinanes were obtained stereoselectively from a two-step sequence, via a phase transfer catalyzed reaction.
• An unusual rearrangement was observed leading to furanosylphosphinic acid.
• In vitro biological tests on several cell lines, highlighted their antiproliferative properties at nanomolar concentration.

This paper describes the preparation and the biological evaluation of α-halogenated oxaphosphinanes. These halogen derivatives were synthetized from a short and stereoselective synthetic sequence starting by previously described hydroxy-precursors 1 and 2 with respectively a glucose and mannose-like configuration. The in vitro biological tests of these unnatural halogenated phosphinosugars, on several cell lines, highlighted, for some of them, their antiproliferative and anti migration and invasion properties at nanomolar concentration.

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