
%0 Journal Article
%A Abbenante, G 
%A Hughes, R 
%A Prager, RH 
%T Potential GABA<sub>B</sub> Receptor Antagonists. VII. The Synthesis of 2-(4-Chlorophenyl)-3-nitropropan-1-amine and Related Analogs of Baclofen
%J Australian Journal of Chemistry
%D 1994/08/01
%V 47
%N 8
%P 1441-1452
%K 
%R https://doi.org/10.1071/CH9941441
%U https://www.publish.csiro.au/paper/CH9941441 
%X 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. 
