Synthesis and antiviral evaluation of 6'-acylamido-6'-deoxy-α-D-mannoglycerolipids

Carbohydr Res. 2013 Nov 15:381:74-82. doi: 10.1016/j.carres.2013.08.010. Epub 2013 Aug 23.

Abstract

Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute α-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9μM.

Keywords: Aminoglycoglycerolipid; Glycosylation; Influenza A virus; α-Anomeric selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Carbohydrate Conformation
  • Cells
  • Dogs
  • Dose-Response Relationship, Drug
  • Glycolipids / chemical synthesis
  • Glycolipids / chemistry
  • Glycolipids / pharmacology*
  • Influenza A virus / drug effects*
  • Madin Darby Canine Kidney Cells / drug effects
  • Madin Darby Canine Kidney Cells / virology
  • Microbial Sensitivity Tests
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Glycolipids