Synthesis and Cytoxicity of Sempervirine and Analogues

J Org Chem. 2016 Mar 4;81(5):2194-200. doi: 10.1021/acs.joc.6b00022. Epub 2016 Feb 10.

Abstract

Sempervirine and analogues were synthesized using a route featuring Sonogashira and Larock Pd-catalyzed reactions. Structure-activity relationships were investigated using three human cancer cell lines. 10-Fluorosempervirine is the most potently cytotoxic member of the family yet described.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Catalysis
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Palladium / chemistry*
  • Secologanin Tryptamine Alkaloids / chemical synthesis*
  • Secologanin Tryptamine Alkaloids / chemistry
  • Secologanin Tryptamine Alkaloids / pharmacology*
  • Structure-Activity Relationship

Substances

  • 10-fluorosempervirine
  • Antineoplastic Agents
  • Secologanin Tryptamine Alkaloids
  • Palladium
  • sempervirine