Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity

Bioorg Med Chem Lett. 2017 May 15;27(10):2181-2184. doi: 10.1016/j.bmcl.2017.03.051. Epub 2017 Mar 22.

Abstract

A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.

Keywords: Acetylenes; Antivirals; Azides; Camphor; Click chemistry; Imine derivatives; Influenza; Triazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Camphor / analogs & derivatives*
  • Camphor / chemical synthesis
  • Camphor / chemistry
  • Camphor / pharmacology
  • Click Chemistry
  • Dogs
  • Ethanolamines / chemical synthesis
  • Ethanolamines / chemistry*
  • Ethanolamines / pharmacology
  • Humans
  • Influenza A Virus, H1N1 Subtype / drug effects
  • Madin Darby Canine Kidney Cells
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Ethanolamines
  • camphecene
  • Camphor