The synthesis of nucleoside 5'-O-(1,1-dithiotriphosphates)

J Med Chem. 1994 Oct 28;37(22):3850-4. doi: 10.1021/jm00048a021.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Cell Line
  • HIV Reverse Transcriptase
  • HIV-1 / drug effects
  • HIV-1 / physiology
  • HIV-2 / drug effects
  • HIV-2 / physiology
  • Reverse Transcriptase Inhibitors
  • Thionucleotides / chemical synthesis*
  • Thionucleotides / pharmacology
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Reverse Transcriptase Inhibitors
  • Thionucleotides
  • HIV Reverse Transcriptase