Synthesis and receptor binding of N-substituted tropane derivatives. High-affinity ligands for the cocaine receptor.

@article{Milius1991SynthesisAR,
  title={Synthesis and receptor binding of N-substituted tropane derivatives. High-affinity ligands for the cocaine receptor.},
  author={Richard A. Milius and Jayanta K. Saha and Bertha K Madras and John L Neumeyer},
  journal={Journal of medicinal chemistry},
  year={1991},
  volume={34 5},
  pages={
          1728-31
        }
}
The synthesis and pharmacological characterization of a series of N-substituted 3-(4-fluorophenyl)tropane derivatives is reported. The compounds displayed binding characteristics that paralleled those of cocaine, and several had substantially higher affinity at cocaine recognition sites. Conjugate addition of 4-fluorophenyl magnesium bromide to anhydroecgonine methyl ester gave 2 beta-(carbomethoxy)-3 beta-(4-fluorophenyl)tropane (4a, designated CFT, also known as WIN 35,428) after flash… 

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TLDR
The synthesis of (E)-N-(3-iodoprop-2-enyl)-2β-carbomethoxy-3β-(3', 4'-dichlorophenyl) nortropane and its radioiodinated analogues is described and the radiolabelling of β-CDIT with 125 I or 123 I that could be used for in vitro and in vivo exploration of the doparnine transporter is reported.
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