TY - JOUR A1 - Wenzel, B. A1 - Li, Y. A1 - Kraus, Werner A1 - Sorger, D. A1 - Sabri, O. A1 - Brust, P. A1 - Steinbach, J. T1 - Pyrrolovesamicols - synthesis, structure and VAChT binding of two 4-fluorobenzoyl regioisomers JF - Bioorganic & medicinal chemistry letters N2 - 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 (Κi = 312 ± 73 nM for (±)-6a and Κi = 7320 ± 1840 nM for (±)-6b) were determined by competitive binding analysis using a cell line stably transfected with ratVAChT and (–)-[3H]vesamicol. KW - Pyrrolovesamicol KW - Vesamicol KW - VAChT KW - Pyrrole PY - 2012 DO - https://doi.org/10.1016/j.bmcl.2012.01.127 SN - 0960-894X SN - 1464-3405 VL - 22 IS - 6 SP - 2163 EP - 2166 PB - Pergamon, Elsevier Science CY - New York, NY [u.a.] AN - OPUS4-25574 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -