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Bioorg Med Chem Lett. 2018 Apr 24. pii: S0960-894X(18)30369-X. doi: 10.1016/j.bmcl.2018.04.057. [Epub ahead of print]
Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses.
Ilyina IV1, Zarubaev VV2, Lavrentieva IN2, Shtro AA3, Esaulkova IL4, Korchagina DV5, Borisevich SS6, Volcho KP7, Salakhutdinov NF1.
Author information
Abstract
A set of (-)-isopulegol derived octahydro-2H-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 (4R)-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. (4R)-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.
KEYWORDS:
Antiviral; Chromene; Influenza; Monoterpene; Montmorillonite K10
PMID: 29716780 DOI: 10.1016/j.bmcl.2018.04.057
Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses.
Ilyina IV1, Zarubaev VV2, Lavrentieva IN2, Shtro AA3, Esaulkova IL4, Korchagina DV5, Borisevich SS6, Volcho KP7, Salakhutdinov NF1.
Author information
Abstract
A set of (-)-isopulegol derived octahydro-2H-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 (4R)-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. (4R)-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.
KEYWORDS:
Antiviral; Chromene; Influenza; Monoterpene; Montmorillonite K10
PMID: 29716780 DOI: 10.1016/j.bmcl.2018.04.057