Amphimedosides A-C: synthesis, chemoselective glycosylation, and biological evaluation

J Org Chem. 2013 Feb 15;78(4):1670-6. doi: 10.1021/jo302640y. Epub 2013 Feb 7.

Abstract

The amphimedosides, discovered in 2006, are the first examples of naturally occurring glycosylated alkoxyamines. We report syntheses of amphimedosides A-C that feature a stereoselective oxyamine neoglycosylation and found that these alkaloids display modest cytotoxicity toward seven diverse human cancer cell lines, exhibiting IC(50) values ranging from 3.0 μM to greater than 100 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Alkaloids / toxicity
  • Amino Sugars / chemical synthesis*
  • Amino Sugars / chemistry
  • Amino Sugars / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Glycosylation
  • Humans
  • Inhibitory Concentration 50
  • Stereoisomerism

Substances

  • Alkaloids
  • Amino Sugars
  • Antineoplastic Agents
  • amphimedoside A
  • amphimedoside B
  • amphimedoside C