Privileged structure based ligands for melanocortin receptors--substituted benzylic piperazine derivatives

Bioorg Med Chem Lett. 2005 Nov 15;15(22):4973-8. doi: 10.1016/j.bmcl.2005.08.018.

Abstract

Replacement of the aryl piperazine moiety in compound 1 with a variety of substituted benzylic piperazines (6) yields compounds that afford melanocortin receptor 4 (MCR4) activity. Analogs with ortho substitution on the aromatic ring afforded the highest affinity. Resolution of the stereocenter of the benzylic piperazine based privileged structure revealed that the R-enantiomer was more active.

MeSH terms

  • Benzene Derivatives / chemistry*
  • Benzene Derivatives / metabolism*
  • Ligands
  • Molecular Structure
  • Piperazine
  • Piperazines / chemistry*
  • Piperazines / metabolism*
  • Receptors, Melanocortin / antagonists & inhibitors
  • Receptors, Melanocortin / metabolism*
  • Structure-Activity Relationship

Substances

  • Benzene Derivatives
  • Ligands
  • Piperazines
  • Receptors, Melanocortin
  • Piperazine