Synthesis and structure-activity relationship of novel lactam-fused chroman derivatives having dual affinity at the 5-HT(1A) receptor and the serotonin transporter

Bioorg Med Chem Lett. 2010 Jan 1;20(1):222-7. doi: 10.1016/j.bmcl.2009.10.134. Epub 2009 Oct 31.

Abstract

The structure-activity relationship (SAR) for three series of lactam-fused chroman derivatives possessing 3-amino substituents was evaluated. Many compounds exhibited affinities for both the 5-HT(1A) receptor and the 5-HT transporter. Compounds 45 and 53 demonstrated 5-HT(1A) antagonist activities in the in vitro cAMP turnover model.

MeSH terms

  • Chromans / chemical synthesis
  • Chromans / chemistry*
  • Chromans / pharmacology
  • Cyclic AMP / metabolism
  • Drug Design
  • Lactams / chemistry*
  • Receptor, Serotonin, 5-HT1A / metabolism
  • Selective Serotonin Reuptake Inhibitors / chemical synthesis*
  • Selective Serotonin Reuptake Inhibitors / chemistry
  • Selective Serotonin Reuptake Inhibitors / pharmacology
  • Serotonin 5-HT1 Receptor Antagonists*
  • Serotonin Plasma Membrane Transport Proteins / chemistry
  • Serotonin Plasma Membrane Transport Proteins / metabolism*
  • Structure-Activity Relationship

Substances

  • Chromans
  • Lactams
  • Serotonin 5-HT1 Receptor Antagonists
  • Serotonin Plasma Membrane Transport Proteins
  • Serotonin Uptake Inhibitors
  • Receptor, Serotonin, 5-HT1A
  • Cyclic AMP