Design and synthesis of 4-arylpiperidinyl amide and N-arylpiperdin-3-yl-cyclopropane carboxamide derivatives as novel melatonin receptor ligands

Bioorg Med Chem Lett. 2011 Feb 15;21(4):1236-42. doi: 10.1016/j.bmcl.2010.12.068. Epub 2010 Dec 19.

Abstract

Two series of 4-arylpiperidinyl amide and N-arylpiperdin-3-yl-cyclopropane carboxamide derivatives exhibiting diverse functionality at rat MT(1) and MT(2) receptors are reported. Compounds 11f and 18b (MT(1)/MT(2) agonist) have human microsomal intrinsic clearance comparable to ramelteon.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / pharmacology
  • Animals
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Cyclopropanes / pharmacology
  • Drug Design
  • Humans
  • Ligands
  • Microsomes / metabolism
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / pharmacology
  • Rats
  • Receptor, Melatonin, MT1 / agonists*
  • Receptor, Melatonin, MT1 / metabolism
  • Receptor, Melatonin, MT2 / agonists*
  • Receptor, Melatonin, MT2 / metabolism
  • Structure-Activity Relationship

Substances

  • Amides
  • Cyclopropanes
  • Ligands
  • Piperidines
  • Receptor, Melatonin, MT1
  • Receptor, Melatonin, MT2