Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

Bioorg Med Chem. 2010 Jan 15;18(2):839-48. doi: 10.1016/j.bmc.2009.11.047. Epub 2009 Nov 29.

Abstract

Chemotherapy and chemoprophylaxis of influenza is one of the most important directions of health protection activity. Due to the high rate of drug-resistant strains of influenza virus, there is a need for the search and further development of new potent antivirals against influenza with a broad spectrum of activity. In the present study, a set of di-, tri- and tetrazole derivatives of adamantane was efficiently prepared and their anti-influenza activities evaluated against rimantadine-resistant strain A/Puerto Rico/8/34. In general, derivatives of tetrazole possessed the highest virus-inhibiting activity. We demonstrated that several compounds of this set exhibited much higher activity than the currently used antiviral rimantadine, a compound of related structure. Moreover, we showed that these azolo-adamantanes were significantly less toxic. This study demonstrates that influenza viruses can be inhibited by adamantyl-azoles and thus have potential for developing antiviral agents with an alternate mechanism of action.

MeSH terms

  • Adamantane / chemical synthesis
  • Adamantane / chemistry
  • Adamantane / pharmacology*
  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Azoles / chemical synthesis
  • Azoles / chemistry
  • Azoles / pharmacology*
  • Cell Line
  • Dogs
  • Influenza A virus / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Azoles
  • Adamantane