Synthesis of some 3',5'-dideoxy-5'-C-phosphonomethyl nucleosides.
Ammonium [1-(3',5',6'-trideoxy-beta-D-erythro-hexofuranosyl)thymine]-6'- phosphonate (1), ammonium 3',5'-dideoxycytidine-5'-C-methylphosphonate (2) and 3',5'-dideoxyadenosine-5'-C-methyl phosphonic acid (3) have been synthesized and tested for anti-HIV activity. The key steps involved an Arbuzov reaction between triethyl phosphite and 3,5,6-trideoxy-6-iodo-1,2-O-isopropylidene-alpha-D-erythro- hexofuranose (7), followed by condensation with the appropriate nucleoside bases. The substances 1, 2 and 3 have been tested in vitro against HIV.
Ioannidis
P
P
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Classon
B
B
Samuelsson
B
B
Kvarnström
I
I
D000998:Antiviral Agents / Q000138:chemical synthesis*; D002478:Cells, Cultured; D006678:HIV / Q000187:drug effects*; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D009705:Nucleosides; D063065:Organophosphonates