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

European journal of medicinal chemistry (2015-10-05)
Rachida Babouri, Marc Rolland, Odile Sainte-Catherine, Zahia Kabouche, Marc Lecouvey, Norbert Bakalara, Jean-Noël Volle, David Virieux, Jean-Luc Pirat
RESUMEN

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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