Pyrrolovesamicols—Synthesis, structure and VAChT binding of two 4-fluorobenzoyl regioisomers
2012
Wenzel, Barbara | Li, Yan | Kraus, Werner | Sorger, Dietlind | Sabri, Osama | Brust, Peter | Steinbach, Jörg
This Letter describes the synthesis of two regioisomers of a new class of vesamicol analogs as possible ligands for imaging the vesicular acetylcholine transporter in future PET studies. The two pyrrolovesamicols (±)-6a and (±)-6b were synthesized by nucleophilic ring opening reaction of a tetrahydroindole epoxide precursor with 4-phenylpiperidine. The reaction mechanism of the synthesis was studied by HPLC and the molecular structures were determined by X-ray structure analysis. Unexpected low binding affinities to VAChT (Kᵢ=312±73nM for (±)-6a and Kᵢ=7320±1840nM for (±)-6b) were determined by competitive binding analysis using a cell line stably transfected with ratVAChT and (−)-[³H]vesamicol.
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