Highly potent activity of isopulegol-derived substituted octahydro-2 H -chromen-4-ols against influenza A and B viruses

Abstract A set of (−)-isopulegol derived octahydro-2 H -chromen-4-ols was synthesized and evaluated in vitro for antiviral activity against panel of reference influenza virus strains differing in subtype, origin (human or avian) and drug resistance. Compound (4 R )- 11a produced via one-pot synthesis by interaction between (−)-isopulegol and acetone was found to exhibit an outstanding activity against a number of H1N1 and H2N2 influenza virus strains with selectivity index more than 1500. (4 R )- 11a was shown to be most potent at early stages of viral cycle. Good correlation between anti-viral activity and calculated binding energy to hemagglutinin TBHQ active site was demonstrated.