Synthesis and anti-retroviral activity of O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) phosphoramidate derivatives.
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.
Kers
I
I
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Stawiński
J
J
Girardet
J L
JL
Imbach
J L
JL
Périgaud
C
C
Gosselin
G
G
Aubertin
A M
AM
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
D000577:Amides; D019380:Anti-HIV Agents; D009705:Nucleosides; D010756:Phosphoric Acids; D011355:Prodrugs; D015215:Zidovudine; C011067:phosphoramidic acid