GABA agonists and uptake inhibitors. Synthesis, absolute stereochemistry, and enantioselectivity of (R)-(-)-and (S)-(+)-homo-. beta.-proline

L Nielsen, L Brehm… - Journal of medicinal …, 1990 - ACS Publications
The structure-activity relationships for the cyclic GABA analogues (RS)-piperidine-3-acetic
acid and (fiS)-homod-proline emphasize the pronounced ligand/inhibitor specificity of GABA …

Partial GABAA receptor agonists. synthesis and in vitro pharmacology of a series of nonannulated analogs of 4, 5, 6, 7-tetrahydroisoxazolo [4, 5-c] pyridin-3-ol

B Frolund, U Kristiansen, L Brehm… - Journal of medicinal …, 1995 - ACS Publications
4-Aminobutanoic acid (GABA, 1) is the majorinhibitory neurotransmitter in the mammalian
central nervous system (CNS) and operates through GABAa, GABAb, and probably also …

Novel cyclic γ-hydroxybutyrate (GHB) analogs with high affinity and stereoselectivity of binding to GHB sites in rat brain

…, B Nielsen, B Frųlund, L Brehm… - … of Pharmacology and …, 2005 - ASPET
γ-Hydroxybutyrate (GHB) is a psychotropic compound endogenous to the brain. Despite its
potentially great physiological significance, its exact molecular mechanism of action is …

Selective inhibitors of glial GABA uptake: synthesis, absolute stereochemistry, and pharmacology of the enantiomers of 3-hydroxy-4-amino-4, 5, 6, 7-tetrahydro-1, 2 …

…, LM Hansen, K Frydenvang, L Brehm… - Journal of medicinal …, 1999 - ACS Publications
3-Methoxy-4,5,6,7-tetrahydro-1,2-benzisoxazol-4-one (20a), or the corresponding 3-ethoxy
analogue (20b), and 3-chloro-4,5,6,7-tetrahydro-1,2-benzisothiazol-4-one (51) were …

Synthesis and pharmacology of highly selective carboxy and phosphono isoxazole amino acid AMPA receptor antagonists

U Madsen, B Bang-Andersen, L Brehm… - Journal of medicinal …, 1996 - ACS Publications
(RS)-2-Amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA, 5) and the
selective AMPA receptor antagonist (RS)-2-amino-3-[3-(carboxymethoxy)-5-methyl-4-isoxazolyl]…

Novel high-affinity and selective biaromatic 4-substituted γ-hydroxybutyric acid (GHB) analogues as GHB ligands: Design, synthesis, and binding studies

…, IF Dahl, H Brauner-Osborne, L Brehm… - Journal of medicinal …, 2008 - ACS Publications
γ-Hydroxybutyrate (GHB) is a metabolite of γ-aminobutyric acid (GABA) and has been
proposed to function as a neurotransmitter or neuromodulator. GHB is used in the treatment of …

Synthesis and structure-activity studies on excitatory amino acids structurally related to ibotenic acid

P Krogsgaard-Larsen, L Brehm… - Journal of medicinal …, 1985 - ACS Publications
With use of ibotenic acid as a lead, analogues of (fiS)-«-amino-3-hydroxy-5-methylisoxazole-4-propionicacid
(AMPA) and of (RS)-3-hydroxy-4, 5, 6, 7-tetrahydroisoxazolo [5, 4-c] …

Resolution, absolute stereochemistry, and pharmacology of the S-(+)-and R-(-)-isomers of the apparent partial AMPA receptor agonist (R, S)-2-amino-3-(3-hydroxy-5 …

B Ebert, S Lenz, L Brehm, P Bregnedal… - Journal of medicinal …, 1994 - ACS Publications
This effect of 5 was insensitive to the NMDA antagonist CPP but was inhibited competitively
by the non-NMDA antagonist NBQX (pK”= 6.30). Compound 6, on the other hand, turned out …

(S)-2-Amino-3-(3-hydroxy-7,8-dihydro-6H-cyclohepta[d]isoxazol-4-yl)propionic Acid, a Potent and Selective Agonist at the GluR5 Subtype of Ionotropic Glutamate …

L Brehm, JR Greenwood, KB Hansen… - Journal of medicinal …, 2003 - ACS Publications
We have previously described (RS)-2-amino-3-(3-hydroxy-7,8-dihydro-6H-cyclohepta[d]isoxazol-4-yl)propionic
acid (4-AHCP) as a highly effective agonist at non-N-methyl-d-aspartate (…

Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure− activity relationships

E Falch, L Brehm, I Mikkelsen… - Journal of medicinal …, 1998 - ACS Publications
We have previously shown that (S)-2-amino-3-(3-hydroxy-5-phenyl-4-isoxazolyl)propionic
acid [(S)-APPA, 2] is a weak agonist at (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)…