Synthesis and binding affinities of 2 beta-(3-iodoallyloxycarbonyl)-3 beta-(4-substituted-aryl)tropane analogues as ligands for the dopamine transporter studies

K H Chung; C H Lim; D R Lee; C Jin; D Y Chi

doi:10.1016/s0960-894x(01)00625-4

Synthesis and binding affinities of 2 beta-(3-iodoallyloxycarbonyl)-3 beta-(4-substituted-aryl)tropane analogues as ligands for the dopamine transporter studies

Bioorg Med Chem Lett. 2001 Dec 3;11(23):3077-80. doi: 10.1016/s0960-894x(01)00625-4.

Authors

K H Chung¹, C H Lim, D R Lee, C Jin, D Y Chi

Affiliation

¹ Department of Chemistry, Inha University, 253 Yonghyundong, Namgu, Inchon, 402-751, Republic of Korea.

PMID: 11714614
DOI: 10.1016/s0960-894x(01)00625-4

Abstract

Tropane analogues from cocaine, which is known to be one of the most reinforcing and addictive compounds, were designed, synthesized, and characterized for inhibition of presynaptic uptake of dopamine (DA) in brain. Eight new derivatives of 3 beta-aryl-2 beta-(3-iodoallyloxycarbonyl)tropanes were synthesized and tested for their potential abilities to displace [(3)H]2 beta-carbomethoxy-3 beta-(4-fluorophenyl)tropane (WIN 35,428) binding to the rat striatal membranes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Binding, Competitive
Biochemistry / methods
Cell Membrane / metabolism
Cocaine / analogs & derivatives*
Cocaine / metabolism
Dopamine / pharmacokinetics
Dopamine Plasma Membrane Transport Proteins
Inhibitory Concentration 50
Ligands
Membrane Glycoproteins*
Membrane Transport Proteins / analysis
Membrane Transport Proteins / metabolism*
Nerve Tissue Proteins*
Rats
Structure-Activity Relationship
Tropanes / chemistry

Substances

Dopamine Plasma Membrane Transport Proteins
Ligands
Membrane Glycoproteins
Membrane Transport Proteins
Nerve Tissue Proteins
Tropanes
(1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
Cocaine
Dopamine