Potential GABAB Receptor Antagonists. V. The Application of Radical Additions to Styrenes to Produce 2-Hydroxysaclofen

1992 ◽  
Vol 45 (11) ◽  
pp. 1791 ◽  
Author(s):  
G Abbenante ◽  
RH Prager
Keyword(s):  
Free Radical ◽  
Gabab Receptor ◽  
Receptor Site ◽  
Radical Addition ◽  
Receptor Antagonists ◽  
The Third ◽  
Potent Antagonist ◽  
Gabab Receptor Antagonists ◽  
Free Radical Addition

3-Amino-2-(4-chlorophenyl)-2-hydroxypropanesulfonic acid (2-hydroxysaclofen), and its 2- phenyl analogue have been synthesized by three methods. Two involve the oxygen- catalysed free radical addition of bisulfite to the corresponding 3-aminopropene or 3-phthalimidopropene, and the third involves the sulfite opening of the epoxide of the phthalimidopropene. 2-Hydroxysaclofen is a potent antagonist of GABA and baclofen at the GABAB receptor site.

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.

Potential GABAB Receptor Antagonists. VI. The Synthesis of Saclofen and Other Sulfonic Acid Derivatives

1992 ◽  
Vol 45 (11) ◽  
pp. 1801 ◽  
Author(s):  
G Abbenante ◽  
RH Prager
Keyword(s):  
Sulfonic Acid ◽  
Gabab Receptor ◽  
Sulfonyl Chloride ◽  
Radical Addition ◽  
Hydroxy Derivative ◽  
Thioacetic Acid ◽  
Receptor Antagonists ◽  
Specific Antagonist ◽  
Gabab Receptor Antagonists

Saclofen, 3-amino-2-(4chlorophenyl) propanesulfonic acid (3), has been synthesized by two routes. Attempts to hydrogenolyse or dehydrate the 2-hydroxy derivative were unsuccessful, however. Radical sulfonation of 3-amino-1-bromo-2-(4-chlorophenyl) propene gave 3-amino-2- (4-chlorophenyl)propene-1-sulfonic acid (6) which was readily reduced to (3). Alternatively, 2-(4-chlorophenyl)-3-phthalimidopropene underwent radical addition of thioacetic acid, and oxidation of the product to the sulfonyl chloride and hydrolysis gave (3). The corresponding sulfonamide (4) was also prepared. The acid (3) is a powerful specific antagonist of GABA at the GABAB receptor, while (4) and (6) are only weak antagonists.

ChemInform Abstract: FREE-RADICAL ADDITION OF ALKANETHIOLS TO 1-VINYLPYRROLES

1978 ◽  
Vol 9 (20) ◽  
Author(s):  
A. I. MIKHALEVA ◽  
S. E. KOROSTOVA ◽  
A. N. VASIL'EV ◽  
L. N. BALABANOVA ◽  
N. P. SOKOL'NIKOVA ◽  
...  
Keyword(s):  
Free Radical ◽  
Radical Addition ◽  
Free Radical Addition

ChemInform Abstract: Free-Radical Addition of Thiolacetic Acid to l-Menthyl and l-Bornyl Fumarates.

ChemInform ◽  
1989 ◽  
Vol 20 (17) ◽  
Author(s):  
Y. OKUDA ◽  
M. YOSHIHARA ◽  
T. MAESHIMA ◽  
N. AMAYA ◽  
Y. MURATA
Keyword(s):  
Free Radical ◽  
Radical Addition ◽  
Free Radical Addition ◽  
Thiolacetic Acid
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