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

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.

• Authors: Yu Liu, Fanbo Jing, Yingying Xu, Yuanchao Xie, Fangyuan Shi, Hao Fang, Minyong Li, Wenfang Xu
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 19 Issue 7 Pg. 2342-8 (Apr 01 2011) ISSN: 1464-3391 [Electronic] England
• PMID: 21382719 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2011 Elsevier Ltd. All rights reserved.

Chemical References

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

Topics

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