3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABA(B) ligands. Synthesis and structure-activity relationship studies

Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on variou...

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Bibliographic Details
Published inEuropean journal of medicinal chemistry Vol. 31; no. 6; pp. 449 - 460
Main Authors Ansar, M, Ebrik, SAA, Mouhoub, R, Berthelot, P, Vaccher, C, Vaccher, MP, Flouquet, N, Caignard, DH, Renard, P, Pirard, B, Rettori, MC, Evrard, G, Durant, F, Debaert, M
Format Journal Article
LanguageEnglish
Published PARIS CEDEX 15 Elsevier 01.01.1996
Subjects
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Science & Technology
ANTAGONIST
ANALOGS
PHARMACOLOGY
B RECEPTOR
GABA(B) ligand
3-heteroaromatic baclofen analogue
structure-activity relationship
BINDING
benzo[b]furan
benzo[b]thiophen
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Summary:Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.
ISSN:0223-5234
DOI:10.1016/0223-5234(96)85165-8