
TY  - JOUR
A1  - Abbenante, G 
A1  - Hughes, R 
A1  - Prager, RH 
T1  - Potential GABA<sub>B</sub> Receptor Antagonists. VII. The Synthesis of 2-(4-Chlorophenyl)-3-nitropropan-1-amine and Related Analogs of Baclofen
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1994
VL  - 47
IS  - 8
SP  - 1441
EP  - 1452
KW  - 
UR  - https://doi.org/10.1071/CH9941441 
N2  - 3-Nitro-2-phenylpropan-1-amine and 2-(4-chloropenyl)-3-nitropropan-1-amine have been synthesized by the addition of nitrous acid to the corresponding trifluoroacetylaminomethylstyrenes followed by reduction of the double bond with sodium borohydride. A more general and efficient route involves the Michael addition of nitroalkane anions to methyl cinnamates followed by Curtius degradation of the corresponding acids. 2-(4-Chlorophenyl)-3-nitropropan-1-amine is a specific agonist of GABA and the GABAB receptor, with about half the activity of racemic baclofen at the isolated guinea pig ileum. Methylation or dimethylation at C3 decreases activity markedly. 
ER  -

