Studies towards the next generation of antidepressants. Part 4: derivatives of 4-(5-fluoro-1H-indol-3-yl)cyclohexylamine with affinity for the serotonin transporter and the 5-HT1A receptor

Bioorg Med Chem Lett. 2005 Feb 15;15(4):911-4. doi: 10.1016/j.bmcl.2004.12.064.

Abstract

Derivatives of the serotonin reuptake inhibitor 4-(5-fluoro-1H-indol-3-yl)cyclohexylamine, in which serotonin 1A (5-HT(1A)) receptor pharmacophoric elements are incorporated, are reported. Analogs exhibiting affinity for both the serotonin transporter and the 5-HT(1A) receptor are described. Compounds containing 1-(4-indolyl)piperazine and 2-(1H-indol-4-yloxy)ethylamine are promising leads for further SAR studies.

MeSH terms

  • Antidepressive Agents / chemical synthesis*
  • Antidepressive Agents / chemistry
  • Cyclohexylamines / chemical synthesis*
  • Cyclohexylamines / chemistry
  • Drug Design
  • Ethylamines
  • Humans
  • Membrane Glycoproteins / chemistry*
  • Membrane Transport Proteins / chemistry*
  • Nerve Tissue Proteins / chemistry*
  • Piperazines
  • Protein Binding
  • Receptor, Serotonin, 5-HT1A / chemistry*
  • Selective Serotonin Reuptake Inhibitors / chemical synthesis*
  • Selective Serotonin Reuptake Inhibitors / chemistry
  • Serotonin Plasma Membrane Transport Proteins
  • Structure-Activity Relationship

Substances

  • Antidepressive Agents
  • Cyclohexylamines
  • Ethylamines
  • Membrane Glycoproteins
  • Membrane Transport Proteins
  • Nerve Tissue Proteins
  • Piperazines
  • SLC6A4 protein, human
  • Serotonin Plasma Membrane Transport Proteins
  • Serotonin Uptake Inhibitors
  • Receptor, Serotonin, 5-HT1A