Conformationally restricted homotryptamines. Part 5: 3-(trans-2-aminomethylcyclopentyl)indoles as potent selective serotonin reuptake inhibitors

Bioorg Med Chem Lett. 2009 Aug 1;19(15):4031-3. doi: 10.1016/j.bmcl.2009.06.026. Epub 2009 Jun 13.

Abstract

A series of racemic 3-(trans-2-aminomethylcyclopentyl)indoles was synthesized and found to have potent binding to the human serotonin transporter (hSERT). The most active analog was synthesized stereospecifically and the active enantiomer was shown to have high affinity binding to hSERT.

MeSH terms

  • Animals
  • Antidepressive Agents / chemistry
  • Chemistry, Pharmaceutical / methods
  • Cyclopentanes / chemistry
  • Dose-Response Relationship, Drug
  • Humans
  • Indoles / chemistry*
  • Inhibitory Concentration 50
  • Ligands
  • Models, Chemical
  • Protein Binding
  • Rats
  • Selective Serotonin Reuptake Inhibitors / chemistry
  • Selective Serotonin Reuptake Inhibitors / pharmacology*
  • Serotonin / chemistry
  • Structure-Activity Relationship
  • Tryptamines / chemistry*

Substances

  • Antidepressive Agents
  • Cyclopentanes
  • Indoles
  • Ligands
  • Serotonin Uptake Inhibitors
  • Tryptamines
  • Serotonin