The synthesis of nucleoside 5'-O-(1,1-dithiotriphosphates).
Appropriately protected nucleoside 5'-O-(2-thio-1,3,2-dithiaphospholanes) react with inorganic pyrophosphate in the presence of a strong base catalyst (DBU) to give nucleoside 5'-O-(1,1-dithiotriphosphates) 1a-g. The latter compounds, including an AZT analogue, show modest antivirial activity against HIV-1 and HIV-2 replication in CEM cells. The AZT and deoxyadenosine derivatives were found to be inhibitors of HIV reverse transcriptase.
Okruszek
A
A
Department of Bioorganic Chemistry, Polish Academy of Sciences, Lodz.
Olesiak
M
M
Balzarini
J
J
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D054303:HIV Reverse Transcriptase; D015497:HIV-1 / Q000187:drug effects / Q000502:physiology; D015498:HIV-2 / Q000187:drug effects / Q000502:physiology; D018894:Reverse Transcriptase Inhibitors; D013873:Thionucleotides / Q000138:chemical synthesis* / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D018894:Reverse Transcriptase Inhibitors; D013873:Thionucleotides; D054303:HIV Reverse Transcriptase