title: α-Halogenated oxaphosphinanes: Synthesis, unexpected reactions and evaluation as inhibitors of cancer cell proliferation.
abstract: 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.
authors.affiliation: ICG Montpellier-UMR 5253, Equipe AM2N, ENSCM, 8, Rue de l'Ecole Normale, 34296 Montpellier CEDEX 5, France; Université Mentouri-Constantine, Département de chimie, Laboratoire d'Obtention de Substances Thérapeutiques (LOST), Campus Chaabet Ersas, 25000 Constantine, Algeria.
authors.forename: Rachida
authors.initials: R
authors.lastname: Babouri
authors.affiliation: Institut Européen des Membranes, cc047 Université de Montpellier 2, 34095 Montpellier, France.
authors.forename: Marc
authors.initials: M
authors.lastname: Rolland
authors.affiliation: Université Paris 13, Sorbonne Paris Cité, CSPBAT, CNRS UMR 7244, 74, Rue Marcel Cachin, F-93017 Bobigny, France.
authors.forename: Odile
authors.initials: O
authors.lastname: Sainte-Catherine
authors.affiliation: Université Mentouri-Constantine, Département de chimie, Laboratoire d'Obtention de Substances Thérapeutiques (LOST), Campus Chaabet Ersas, 25000 Constantine, Algeria.
authors.forename: Zahia
authors.initials: Z
authors.lastname: Kabouche
authors.affiliation: Université Paris 13, Sorbonne Paris Cité, CSPBAT, CNRS UMR 7244, 74, Rue Marcel Cachin, F-93017 Bobigny, France. Electronic address: marc.lecouvey@univ-paris13.fr.
authors.forename: Marc
authors.initials: M
authors.lastname: Lecouvey
authors.affiliation: INSERM U-1051, Institut des Neurosciences de Montpellier, 80 Rue Augustin Fliche, 34091 Montpellier, France.
authors.forename: Norbert
authors.initials: N
authors.lastname: Bakalara
authors.affiliation: ICG Montpellier-UMR 5253, Equipe AM2N, ENSCM, 8, Rue de l'Ecole Normale, 34296 Montpellier CEDEX 5, France. Electronic address: jean-noel.volle@enscm.fr.
authors.forename: Jean-Noël
authors.initials: JN
authors.lastname: Volle
authors.affiliation: ICG Montpellier-UMR 5253, Equipe AM2N, ENSCM, 8, Rue de l'Ecole Normale, 34296 Montpellier CEDEX 5, France. Electronic address: david.virieux@enscm.fr.
authors.forename: David
authors.initials: D
authors.lastname: Virieux
authors.affiliation: ICG Montpellier-UMR 5253, Equipe AM2N, ENSCM, 8, Rue de l'Ecole Normale, 34296 Montpellier CEDEX 5, France.
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Pirat
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002465:Cell Movement / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D054879:Halogenation; D006801:Humans; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D010720:Phosphines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D010720:Phosphines
keywords: Antiproliferative properties; Phase-transfer catalysis; Phosphinosugars; Sigmatropic rearrangement; Triflate halogen exchange; α-Halogenated oxaphosphinanes