Synthesis, inhibition and binding of simple non-nitrogen inhibitors of monoamine transporters

Bioorg Med Chem. 2007 Jun 15;15(12):4159-74. doi: 10.1016/j.bmc.2007.03.069. Epub 2007 Mar 30.

Abstract

A series of simple truncated analogues of phenyl tropanes, 2-arylcycloalk-1-enyl carboxylic acid methylesters, were prepared and investigated for their activity towards the dopamine, serotonin and norepinephrine transporters. The compounds were prepared from cyclic ketoesters, which were converted to enolic triflates and reacted with arylboronates using the Suzuki coupling. For comparison the corresponding piperidines were also made and investigated. The new compounds inhibit monoamine-transporters with Ki values ranging from 0.1 to 1000 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • COS Cells
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology*
  • Chlorocebus aethiops
  • Magnetic Resonance Spectroscopy
  • Nitrogen
  • Spectrometry, Mass, Electrospray Ionization
  • Vesicular Monoamine Transport Proteins / antagonists & inhibitors*

Substances

  • Carboxylic Acids
  • Vesicular Monoamine Transport Proteins
  • Nitrogen