Synthesis of novel МТ3 receptor ligands via an unusual Knoevenagel condensation

Bioorg Med Chem Lett. 2012 Dec 15;22(24):7578-81. doi: 10.1016/j.bmcl.2012.10.005. Epub 2012 Oct 17.

Abstract

New 5-acetamido-substituted melatonin derivatives were efficiently synthesized in excellent yields via Knoevenagel condensation. The relative binding affinity of new synthesized compounds to MT3 receptor was tested via enzymatic assays and the X-ray structures of the most potent compounds were determined in complex with MT3.

MeSH terms

  • Acetamides / chemistry*
  • Crystallography, X-Ray
  • Humans
  • Ligands
  • Melatonin / chemical synthesis
  • Melatonin / chemistry
  • Melatonin / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Receptors, Melatonin / antagonists & inhibitors*

Substances

  • Acetamides
  • Ligands
  • Receptors, Melatonin
  • Melatonin