Acetylenic and allenic derivatives of 2-(1-methylindolyl) methylamine as selective inhibitors of the monoamine oxidases A and B

This paper reports the synthesis of a new series of acetylenic and allenic derivatives of 2-(1-methylindolyl) methylamine as well as the preliminary results of their study as selective inhibitors of the A and B forms of the mitochondrial monoamine oxidase from bovine brain. The compounds were obtained from 2-(1-methylindole)carboxylic acid which, as its acyl halide, reacts with amines to give the respective amides. The latter compounds were reduced with lithium aluminium hydride to the respective amines (II a-c) and then N-alkylated by reaction with 2-propynyl-, 2-butynyl- or 2,3-butadienyl bromides to the corresponding amines (III a-j).