title: An alternative pathway to ribonucleoside β-hydroxyphosphonate analogues and related prodrugs.
abstract: Nucleoside β-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of a β-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM), UMR5247 CNRS-UM1-UM2, Nucleosides and Phosphorylated Effectors Team, University Montpellier 2 , cc 1705, place Eugène Bataillon, 34095 Montpellier cedex 5, France.
authors.forename: Audrey
authors.initials: A
authors.lastname: Hospital
authors.forename: Maïa
authors.initials: M
authors.lastname: Meurillon
authors.forename: Suzanne
authors.initials: S
authors.lastname: Peyrottes
authors.forename: Christian
authors.initials: C
authors.lastname: Périgaud
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009708:Nucleotidases / Q000037:antagonists & inhibitors; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D011355:Prodrugs; D012263:Ribonucleosides; D009708:Nucleotidases