Preparation of 4-azaindole and 7-azaindole dimers with a bisalkoxyalkyl spacer in order to preferentially target melatonin MT1 receptors over melatonin MT2 receptors

Eur J Med Chem. 2004 Jun;39(6):515-26. doi: 10.1016/j.ejmech.2004.03.005.

Abstract

Several 4-azaindole and 7-azaindole dimer analogues of melatonin with a bisalkoxyalkyl spacer between the position 5 of each heterocycle were synthetized. Our aim was to investigate the influence of the spacers length on the selectivity of such compounds for the MT(1) receptors over the MT(2) receptors. Our results suggest the distance between indole ring seems to be an important parameter in determining the potency of binding with melatonin receptor site.

Publication types

  • Comparative Study

MeSH terms

  • Aza Compounds / chemistry*
  • Binding Sites
  • Cell Cycle / drug effects
  • Cross-Linking Reagents / chemistry*
  • Dimerization
  • Humans
  • Indoles / chemistry*
  • Receptor, Melatonin, MT1 / metabolism*
  • Receptor, Melatonin, MT2 / metabolism*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Aza Compounds
  • Cross-Linking Reagents
  • Indoles
  • Receptor, Melatonin, MT1
  • Receptor, Melatonin, MT2