5'-Hydroxy-5'-homoaristeromycin: Synthesis and antiviral properties

Bioorg Med Chem Lett. 2018 May 15;28(9):1456-1458. doi: 10.1016/j.bmcl.2018.03.088. Epub 2018 Mar 31.

Abstract

Synthetically combining the C-4' side-chain structural features of the antiviral candidates 5'-methylaristeromycin and 5'-homoaristeromycin into a diastereomeric pair of C-4' side-chain dihydroxylated aristeromycins (6 and 7) is reported. Broad antiviral analyses of the both targets found promising effects towards HBV (6, 6.7 μM and 7, 7.74 μM) and HCMV (only 7, 0.72 μM). No other activity was found. Neither of the diastereomers was cytotoxic in the assays performed.

Keywords: C-4′ aristeromycin derivatives; Carbocyclic nucleosides; Cytomegalovirus; Hepatitis B.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / chemistry
  • Adenosine / pharmacology
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cytomegalovirus / drug effects*
  • Dose-Response Relationship, Drug
  • Hepatitis B virus / drug effects*
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Structure-Activity Relationship

Substances

  • 5'-homoaristeromycin
  • Antiviral Agents
  • Adenosine