Synthesis of antitumour (1H-1,2,3-triazol-4-yl)-4-hydroxycyclohexa-2,5-dien-1-ones by copper-catalysed Huisgen cycloadditions

Org Biomol Chem. 2010 May 7;8(9):2078-84. doi: 10.1039/b920039h. Epub 2010 Mar 3.

Abstract

4-Ethynyl-4-hydroxycyclohexa-2,5-dien-1-one 5 undergoes cycloaddition reactions with a range of substituted azides in the presence of copper salts to form 1,4-disubstituted triazoles 8-11 bearing the 4-hydroxycyclohexa-2,5-dien-1-one (quinol) pharmacophore; one example of an isomeric 1,5-disubstituted triazole 12 was formed from 5 and benzyl azide in the presence of a ruthenium catalyst. Compounds were screened for growth-inhibitory activity against five cancer cell lines of colon, breast and lung origin, but were overall less potent than the benzothiazolyl- and indolyl-substituted quinols 2 and 3.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Catalysis
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Copper / chemistry*
  • Cyclization
  • Cyclohexanones / chemical synthesis*
  • Cyclohexanones / chemistry
  • Cyclohexanones / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Antineoplastic Agents
  • Cyclohexanones
  • Triazoles
  • Copper