ChemInform Abstract: Potential GABAB Receptor Antagonists. Part 9. The Synthesis of 3-Amino-3-(4-chlorophenyl)propanoic Acid, 2-Amino-2-(4-chlorophenyl)ethylphosphonic Acid and 2-Amino-2-(4-chlorophenyl)ethanesulfonic Acid.

ChemInform ◽  
2010 ◽  
Vol 28 (48) ◽  
pp. no-no
Author(s):  
G. ABBENANTE ◽  
R. HUGHES ◽  
R. H. PRAGER
Keyword(s):  
Gabab Receptor ◽  
Propanoic Acid ◽  
Receptor Antagonists ◽  
Ethanesulfonic Acid ◽  
Gabab Receptor Antagonists

Potential GABA B Receptor Antagonists. IX The Synthesis of 3-Amino-3-(4-chlorophenyl)propanoic Acid, 2-Amino-2-(4-chlorophenyl)ethylphosphonic Acid and 2-Amino-2-(4-chlorophenyl)ethanesulfonic Acid

1997 ◽  
Vol 50 (6) ◽  
pp. 523 ◽  
Author(s):  
Giovanni Abbenante ◽  
Robert Hughes ◽  
Rolf H. Prager
Keyword(s):  
Carboxylic Acid ◽  
Phosphonic Acid ◽  
Sulfonic Acid ◽  
Gabab Receptor ◽  
Propanoic Acid ◽  
Receptor Antagonists ◽  
Sulfonic Acids ◽  
Ethanesulfonic Acid

This paper describes the synthesis of 3-amino-3-(4-chlorophenyl)propanoic acid and the corresponding phosphonic and sulfonic acids, lower homologues of baclofen, phaclofen and saclofen respectively. The chlorinated acids were all weak specific antagonists of GABA at the GABAB receptor, with the sulfonic acid (pA2 4·0) being stronger than the phosphonic acid (pA2 3·8) and carboxylic acid (pA2 3·5).

GABAB receptor antagonists: from synthesis to therapeutic applications

1993 ◽  
Vol 14 (11) ◽  
pp. 391-394 ◽  
Author(s):  
Helmut Bittiger ◽  
Wolfgang Froestl ◽  
Stuart J. Mickel ◽  
Hans-Rudolf Olpe
Keyword(s):  
Gabab Receptor ◽  
Receptor Antagonists ◽  
Therapeutic Applications ◽  
Gabab Receptor Antagonists

Potential GABAB Receptor Antagonists. III. Folded Baclofen Analogs Based on Phthalide

1989 ◽  
Vol 42 (6) ◽  
pp. 787 ◽  
Author(s):  
C Donati ◽  
RH Prager ◽  
B Weber
Keyword(s):  
Ethyl Acetoacetate ◽  
Gabab Receptor ◽  
Hydrazoic Acid ◽  
Receptor Antagonists ◽  
Keto Ester ◽  
Acidic Conditions ◽  
Gabab Receptor Antagonists ◽  
Hydrolysis Of ◽  
Parallel Series

Possible analogues of baclofen, 3-aminomethyl-5-chloro-, 3-aminomethyl-6-chloro- and 3-aminomethyl-5,6-dichloro-isobenzofuran-1(3H)-one, have been prepared for evaluation as antispasticity agents. The corresponding 3-hydroxyisobenzofuran-l(3H)-one was reacted with ethyl acetoacetate under acidic conditions, and the keto ester hydrolysed and decarboxylated to give the 3-(2-oxopropyl)isobenzofuran-l(3H)-one; this was treated with hydrazoic acid, and the product was hydrolysed. A parallel series of (3-oxo-1,3-dihydroisobenzofuran-1-y1)glycines was obtained by treating the keto ester first with hydrazoic acid, and hydrolysis of the resulting acetamides.

Potential GABAB Receptor Antagonists. VIII. The Synthesis of 3-Amino-N-aryl-2-hydroxy- propane-1-sulfonamides and Analogues of Baclofen Containing Nitro Groups

1997 ◽  
Vol 50 (1) ◽  
pp. 19 ◽  
Author(s):  
Robert Hughes ◽  
Rolf H. Prager
Keyword(s):  
Sodium Azide ◽  
Gabab Receptor ◽  
Amino Group ◽  
Receptor Antagonists ◽  
Gabab Receptor Antagonists

3-Amino-N-aryl-2-hydroxypropane-1-sulfonamides were synthesized by the reaction of the corresponding epoxy sulfonamide with sodium azide, followed by reduction to the corresponding amine. The synthesis of 3-nitropropan-1-amine and two 2-thienyl derivatives is also reported. 3-Amino-2-hydroxy-N-(4-nitrophenyl)propane-1-sulfonamide and 3-nitropropan-1-amine were found to be specific antagonists of GABA at the GABAB receptor. Substitution of the amino group by alkyl or aryl groups reduced the activity.

Morpholin-2-yl-phosphinic acids are potent GABAB receptor antagonists in rat brain

1998 ◽  
Vol 362 (1) ◽  
pp. 27-34 ◽  
Author(s):  
Jennifer Ong ◽  
David I.B. Kerr ◽  
Helmut Bittiger ◽  
Peter C. Waldmeier ◽  
Peter A. Baumann ◽  
...  
Keyword(s):  
Rat Brain ◽  
Gabab Receptor ◽  
Receptor Antagonists ◽  
Phosphinic Acids ◽  
Gabab Receptor Antagonists

AMPA and GABAB receptor antagonists and their interaction in rats with a genetic form of absence epilepsy

2001 ◽  
Vol 430 (2-3) ◽  
pp. 251-259 ◽  
Author(s):  
Rafał M Kamiński ◽  
Clementina M Van Rijn ◽  
Waldemar A Turski ◽  
Stanisław J Czuczwar ◽  
Gilles Van Luijtelaar
Keyword(s):  
Gabab Receptor ◽  
Absence Epilepsy ◽  
Receptor Antagonists ◽  
Gabab Receptor Antagonists ◽  
Genetic Form

Potential GABAB Receptor Antagonists. X The Synthesis of Further Analogues of Baclofen, Phaclofen and Saclofen

1997 ◽  
Vol 50 (8) ◽  
pp. 813 ◽  
Author(s):  
Rolf H. Prager ◽  
Karl Schafer
Keyword(s):  
Hydroxamic Acid ◽  
Gabab Receptor ◽  
Receptor Site ◽  
Binding Activity ◽  
Pentanoic Acid ◽  
Receptor Antagonists ◽  
New Compounds ◽  
Gabab Receptor Antagonists

In an attempt to obtain new compounds with binding activity at the GABAB receptor site, we report the synthesis of 3-amino-2-arylpropanoic acids, and the sulfonic, phosphonic and hydroxamic acid analogues. In addition, we report the synthesis of the isomer of phaclofen, 3-amino-1-(4-chlorophenyl)-propylphosphonic acid, and the higher homologue of baclofen, 5-amino-2-(4-chlorophenyl)pentanoic acid.

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