6'-Fluoro-3-deazaneplanocin: Synthesis and antiviral properties, including Ebola

Bioorg Med Chem Lett. 2018 Dec 15;28(23-24):3674-3675. doi: 10.1016/j.bmcl.2018.10.030. Epub 2018 Oct 22.

Abstract

A convenient stereospecific synthesis of 6'-fluoro-3-deazaneplanocin (6) has been accomplished from d-ribose in 15 steps. It is reported to possess significant activity towards Ebola (Zaire, Vero, μM: EC50 < 0.36; CC50 125; SI > 347) with moderate inhibition of the target enzyme (S-adenosylhomocysteine hydrolase), which did not correlate directly with its anti-Ebola effects. Compound 6, with limited cytotoxicity, also displayed activity against measles, H1N1 and Pichinde.

Keywords: 3-Deazaneplanocin; Carbocyclic nucleosides; Cytomegalovirus; Ebola; H1N1; Measles; Pichinde virus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / chemistry
  • Adenosine / pharmacology
  • Adenosylhomocysteinase / antagonists & inhibitors
  • Adenosylhomocysteinase / metabolism
  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Chlorocebus aethiops
  • Ebolavirus / drug effects
  • Influenza A Virus, H1N1 Subtype / drug effects
  • Inhibitory Concentration 50
  • Vero Cells

Substances

  • Antiviral Agents
  • 3-deazaneplanocin
  • Adenosylhomocysteinase
  • Adenosine