Nitrosopurines en route to potently cytotoxic asmarines.


A nitrosopurine ene reaction easily assembles the asmarine pharmacophore and transmits remote stereochemistry to the diazepine-purine hetereocycle. This reaction generates potent cytotoxins which exceed the potency of asmarine A (1.2 μM IC50) and supersede the metabolites as useful leads for biological discovery.


Wan, Kanny; Iwasaki, Kotaro; Umotoy, Jeffrey C; Wolan, Dennis W; Shenvi, Ryan A;


  • Azepines/ chemistry
  • Cell Survival/ drug effects
  • Cytotoxins/ chemical synthesis
  • Cytotoxins/ chemistry
  • Cytotoxins/ toxicity
  • Diterpenes/ chemical synthesis
  • Diterpenes/ chemistry
  • Diterpenes/ toxicity
  • HT29 Cells
  • Humans
  • Purines/ chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

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