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Synthesis of N-substituted acyclic β-amino acids and their investigation as GABA uptake inhibitors.

Abstract：

:In this publication, we describe the synthesis of new inhibitors for the GABA transporter subtypes GAT1 and especially GAT3. We started with 3-aminopropanoic acid possessing a distinct preference for GAT3 in comparison to GAT1 and furthermore its homolog 3-aminobutanoic acid. A series of respective N-substituted amino acids was synthesized by selective N-monoalkylation of these parent structures with 6 different arylalkyl alcohols via a Mitsunobu-type reaction. The resulting compounds were investigated for their inhibitory potency GABA transporter subtypes. Among all tested compounds the 4,4-diphenylbut-3-enyl substituted 3-aminobutanoic acid (rac)-6b showed highest potency with a pIC50 value of 5.34 at GAT1. Unfortunately, the expected GAT3 potency for 2-[tris(4-methoxyphenyl)methoxy]ethyl substituted derivatives was not as high as observed for the respective nipecotic acid derivatives.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Sitka I,Allmendinger L,Fülep G,Höfner G,Wanner KT

doi

10.1016/j.ejmech.2013.04.063

subject

Has Abstract

pub_date

2013-07-01 00:00:00

pages

487-99

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(13)00295-X

journal_volume

65

pub_type

杂志文章

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