1. α-Halogenated oxaphosphinanes: Synthesis, unexpected reactions and evaluation as inhibitors of cancer cell proliferation
- Author
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Odile Sainte-Catherine, Rachida Babouri, Zahia Kabouche, Jean-Noël Volle, David Virieux, Marc Rolland, Norbert Bakalara, Marc Lecouvey, Jean-Luc Pirat, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM), Chimie, Structures et Propriétés de Biomatériaux et d'Agents Thérapeutiques (CSPBAT), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris 13 (UP13)-Institut Galilée-Université Sorbonne Paris Cité (USPC), Université Mentouri Constantine [Algérie] (UMC), Institut des Neurosciences de Montpellier - Déficits sensoriels et moteurs (INM), and Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Montpellier (UM)
- Subjects
Models, Molecular ,inorganic chemicals ,Halogenation ,Cell Survival ,Phosphines ,Antineoplastic Agents ,Sigmatropic reaction ,Crystallography, X-Ray ,Mice ,Structure-Activity Relationship ,Cell Movement ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,[CHIM]Chemical Sciences ,Structure–activity relationship ,ComputingMilieux_MISCELLANEOUS ,Cell Proliferation ,Biological evaluation ,Pharmacology ,Dose-Response Relationship, Drug ,Molecular Structure ,Cell growth ,Chemistry ,Cancer cell proliferation ,Organic Chemistry ,General Medicine ,3. Good health ,Biochemistry ,Cell culture ,Stereoselectivity ,Drug Screening Assays, Antitumor - 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.
- Published
- 2015