title: Synthesis and anti-retroviral activity of O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) phosphoramidate derivatives.
abstract: A simple and efficient protocol for the preparation of various symmetrical dinucleoside phosphoramidates derived from AZT, is presented. It consists of the phosphonylation of AZT with phosphonic acid in the presence of DCC to produce the symmetrical H-phosphonate diester, followed by its oxidative conversion to various phosphoramidate analogues. The synthesized compounds were evaluated for their anti-HIV activity in different cell cultures.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
authors.forename: I
authors.initials: I
authors.lastname: Kers
authors.forename: J
authors.initials: J
authors.lastname: Stawiński
authors.forename: J L
authors.initials: JL
authors.lastname: Girardet
authors.forename: J L
authors.initials: JL
authors.lastname: Imbach
authors.forename: C
authors.initials: C
authors.lastname: Périgaud
authors.forename: G
authors.initials: G
authors.lastname: Gosselin
authors.forename: A M
authors.initials: AM
authors.lastname: Aubertin
mesh_terms: D000577:Amides / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002478:Cells, Cultured; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010756:Phosphoric Acids / Q000737:chemistry*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects; D015215:Zidovudine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000577:Amides; D019380:Anti-HIV Agents; D009705:Nucleosides; D010756:Phosphoric Acids; D011355:Prodrugs; D015215:Zidovudine; C011067:phosphoramidic acid