Synthesis, inhibition and binding of simple non-nitrogen inhibitors of monoamine transporters.
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.
Petersen
Mikkel Due
MD
Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000 Aarhus C, Denmark.
Boye
Søren Valdgård
SV
Nielsen
Erik Holm
EH
Willumsen
Jeanette
J
Sinning
Steffen
S
Wiborg
Ove
O
Bols
Mikael
M
D000818:Animals; D019556:COS Cells; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen; D021241:Spectrometry, Mass, Electrospray Ionization; D050493:Vesicular Monoamine Transport Proteins / Q000037:antagonists & inhibitors*
D002264:Carboxylic Acids; D050493:Vesicular Monoamine Transport Proteins; D009584:Nitrogen