Discovery of a new class of antiviral compounds: camphor imine derivatives

Eur J Med Chem. 2015 Nov 13;105:263-73. doi: 10.1016/j.ejmech.2015.10.010. Epub 2015 Oct 22.

Abstract

A new class of compounds featuring a camphor moiety has been discovered that exhibits potent inhibitory activity against influenza A(H1N1)pdm09 and A(H5N1) viruses. The synthesized compounds were characterized by spectroscopic analysis; in addition the structures of compound 2 and 14 were elucidated by the X-ray diffraction technique. Structure-activity relationship studies have been conducted to identify the 1,7,7-trimethylbicyclo[2.2.1]heptanes2-ylidene group as the key functional group responsible for the observed antiviral activity. The most potent antiviral compound is imine 2 with therapeutic index more than 500.

Keywords: Antiviral; Cage compounds; Camphor derivatives; Influenza.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Camphor / chemical synthesis
  • Camphor / chemistry
  • Camphor / pharmacology*
  • Dogs
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Imines / chemical synthesis
  • Imines / chemistry
  • Imines / pharmacology*
  • Influenza A Virus, H1N1 Subtype / drug effects*
  • Influenza A Virus, H5N1 Subtype / drug effects*
  • Madin Darby Canine Kidney Cells
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Imines
  • Camphor