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

Irina V. Ilyina, Vladimir V. Zarubaev, Irina N. Lavrentieva, Anna A. Shtro, Iana L. Esaulkova, Dina V. Korchagina, Sophia S. Borisevich, Konstantin P. Volcho, Nariman F. Salakhutdinov

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2061-2067
Number of pages7
JournalBioorganic and Medicinal Chemistry Letters
Volume28
Issue number11
DOIs
Publication statusPublished - 15 Jun 2018

Keywords

  • Antiviral
  • Chromene
  • Influenza
  • Monoterpene
  • Montmorillonite K10
  • MONOTERPENOIDS
  • HEMAGGLUTININ
  • ANALGESIC ACTIVITY
  • DISCOVERY
  • PRINS CYCLIZATION
  • ANTIINFLUENZA ACTIVITY
  • ANTIVIRAL ACTIVITY
  • DERIVATIVES
  • Antiviral Agents/chemical synthesis
  • Structure-Activity Relationship
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests
  • Influenza A virus/drug effects
  • Terpenes/chemical synthesis
  • Influenza B virus/drug effects
  • Molecular Structure

Fingerprint Dive into the research topics of 'Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses'. Together they form a unique fingerprint.

Cite this