Solvent effect on copper-catalyzed azide-alkyne cycloaddition (CuAAC): synthesis of novel triazolyl substituted quinolines as potential anticancer agents

Bioorg Med Chem Lett. 2012 May 15;22(10):3455-9. doi: 10.1016/j.bmcl.2012.03.091. Epub 2012 Mar 30.

Abstract

A regioselective route to novel mono triazolyl substituted quinolines has been developed via copper-catalyzed azide-alkyne cycloaddition (CuAAC) of 2,4-diazidoquinoline with terminal alkynes in DMF. The reaction provided bis triazolyl substituted quinolines when performed in water in the presence of Et(3)N. A number of the compounds synthesized showed promising anti-proliferative properties when tested in vitro especially against breast cancer cells.

MeSH terms

  • Alkynes / chemistry*
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Azides / chemistry*
  • Cell Line, Tumor
  • Copper / chemistry*
  • Cyclization
  • Drug Screening Assays, Antitumor
  • Humans
  • Models, Molecular
  • Quinolines / chemistry*
  • Solvents / chemistry*

Substances

  • Alkynes
  • Antineoplastic Agents
  • Azides
  • Quinolines
  • Solvents
  • Copper