Synthesis of analogues of GABA. IX. 5-(Aminomethyl)-3-hydroxyfuran-2(5H)-one

Abstract

5-(Aminomethyl)-3-hydroxyfuran-2(5 H )-one (4) has been synthesized as a GABA analogue in five steps from hex-3-enedioic acid, the enolic a-keto group being introduced under mild conditions by means of a singlet oxygen cleavage of an enamino lactone. The compound showed negligible activity as a GABA agonist with respect to inhibition of [3H]GABA binding, uptake and trans amination in rat brain membranes