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

Abstract

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.