Filtern
Erscheinungsjahr
- 2012 (1)
Dokumenttyp
Sprache
- Englisch (1)
Referierte Publikation
- ja (1)
Schlagworte
- Pyrrole (1)
- Pyrrolovesamicol (1)
- VAChT (1)
- Vesamicol (1)
Pyrrolovesamicols - synthesis, structure and VAChT binding of two 4-fluorobenzoyl regioisomers
(2012)
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.