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Pyrrolovesamicols--synthesis, structure and VAChT binding of two 4-fluorobenzoyl regioisomers.

Abstract：

: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 (K(i)=312±73 nM for (±)-6a and K(i)=7320±1840 nM for (±)-6b) were determined by competitive binding analysis using a cell line stably transfected with ratVAChT and (-)-[(3)H]vesamicol.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Wenzel B,Li Y,Kraus W,Sorger D,Sabri O,Brust P,Steinbach J

doi

10.1016/j.bmcl.2012.01.127

subject

Has Abstract

pub_date

2012-03-15 00:00:00

pages

2163-6

issue

6

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(12)00169-2

journal_volume

22

pub_type

杂志文章

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