171236-00-3Relevant academic research and scientific papers
Synthesis and 11C-Radiolabelling of a Tropane Derivative Lacking the 2β Ester Group: A Potential PET-Tracer for the Dopamine Transporter
Schoenbaechler, Roland,Ametamey, Simon M.,Schubiger, Pius A.
, p. 447 - 456 (2007/10/03)
The synthesis and 11C-radiolabelling of a new tropane analogue, 3β-(4'-chlorophenyl)-2β-(3'-phenylisoxazol-5'-yl)tropane (β-CPPIT), an inhibitor of the dopamine transporter, is reported. The desmethyl compound, 3β-(4'-chlorophenyl)-2β-(3'-phenylisoxazol-5'-yl)nortropane (5) was prepared via a six-step reaction sequence starting from cocaine. [11C]-β-CPPIT was labelled by N-methylation using [11C]-methyl iodide obtained from the gas phase reaction of [11C]-methane with iodine in 60 +/- 10 percent radiochemical yield (decay corrected from [11C]-methyl iodide). The overall synthesis time was on average 60 minutes at EOB (end of bombardment). The final product had a specific activity of 2000 - 2700 Ci/mmol (74 - 100 TBq/mmol) at EOS (end of synthesis) and the radiochemical purity was greater than 99 percent. [11C]-β-CPPIT showed a logP value of 2.1 indicating that a free diffusion through the blood-brain-barrier should be possible.
Synthesis, ligand binding, and quantitative structure-activity relationship study of 3β-(4'-substituted phenyl)-2β-heterocyclic tropanes: Evidence for an electrostatic interaction at the 2β-position
Kotian, Pravin,Mascarella, S. Wayne,Abraham, Philip,Lewin, Anita H.,Boja, John W.,Kuhar, Michael J.,Carroll, F. Ivy
, p. 2753 - 2763 (2007/10/03)
A set of 3β-(4'-substituted phenyl)-2β-heterocyclic tropanes was designed, synthesized, and characterized. We discovered that these compounds can function as bioisosteric replacements for the corresponding WIN 35,065-2 analogs which possess a 2β-carbometh
