Thiophene derivatives: a new series of potent norepinephrine and serotonin reuptake inhibitors

Bioorg Med Chem Lett. 2002 Apr 8;12(7):993-5. doi: 10.1016/s0960-894x(02)00103-8.

Abstract

A series of (1S,3S,6R,10S)-(Z)-9-(thienylmethylene- or substituted thienylmethylene)-7-azatricyclo[4.3.1.0(3,7)]decanes was prepared and evaluated for the ability to block dopamine, serotonin, and norepinephrine reuptake by their respective transporters. Compound 5b is a NET-selective inhibitor, 5c is a mixed NET- and SERT-selective inhibitor, while 11 is a SERT-selective inhibitor.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Brain / drug effects
  • Brain / metabolism
  • Carrier Proteins / metabolism
  • Dopamine Plasma Membrane Transport Proteins
  • Ligands
  • Membrane Glycoproteins / metabolism
  • Membrane Transport Proteins / metabolism
  • Molecular Conformation
  • Nerve Tissue Proteins*
  • Neurotransmitter Uptake Inhibitors / chemical synthesis
  • Neurotransmitter Uptake Inhibitors / pharmacology*
  • Norepinephrine / physiology*
  • Norepinephrine Plasma Membrane Transport Proteins
  • Rats
  • Selective Serotonin Reuptake Inhibitors / chemical synthesis
  • Selective Serotonin Reuptake Inhibitors / pharmacology*
  • Serotonin / physiology
  • Serotonin Plasma Membrane Transport Proteins
  • Stereoisomerism
  • Structure-Activity Relationship
  • Symporters / metabolism
  • Thiophenes / chemical synthesis
  • Thiophenes / pharmacology*

Substances

  • Carrier Proteins
  • Dopamine Plasma Membrane Transport Proteins
  • Ligands
  • Membrane Glycoproteins
  • Membrane Transport Proteins
  • Nerve Tissue Proteins
  • Neurotransmitter Uptake Inhibitors
  • Norepinephrine Plasma Membrane Transport Proteins
  • Serotonin Plasma Membrane Transport Proteins
  • Serotonin Uptake Inhibitors
  • Slc6a2 protein, rat
  • Slc6a4 protein, rat
  • Symporters
  • Thiophenes
  • Serotonin
  • Norepinephrine