Design, synthesis and biological activity of thiazolidine-4-carboxylic acid derivatives as novel influenza neuraminidase inhibitors

Bioorg Med Chem. 2011 Apr 1;19(7):2342-8. doi: 10.1016/j.bmc.2011.02.019. Epub 2011 Feb 17.

Abstract

A series of thiazolidine-4-carboxylic acid derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus. All the compounds were synthesized in good yields starting from commercially available l-cysteine hydrochloride using a suitable synthetic strategy. These compounds showed moderate inhibitory activity against influenza A neuraminidase. The most potent compound of this series is compound 4f (IC(50)=0.14 μM), which is about sevenfold less potent than oseltamivir and could be used to design novel influenza NA inhibitors that exhibit increased activity based on thiazolidine ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Drug Design
  • Influenza A Virus, H3N2 Subtype / enzymology*
  • Models, Molecular
  • Neuraminidase / antagonists & inhibitors*
  • Neuraminidase / chemistry
  • Oseltamivir / chemistry
  • Oseltamivir / pharmacology
  • Thiazolidines / chemical synthesis
  • Thiazolidines / chemistry*
  • Thiazolidines / pharmacology*

Substances

  • Antiviral Agents
  • Thiazolidines
  • Oseltamivir
  • thiazolidine-4-carboxylic acid
  • Neuraminidase