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).
Cruces
M A
MA
Instituto de Química Orgánica General del CSIC, Madrid, Spain.
Elorriaga
C
C
Fernandez Alvarez
E
E
Lopez Chico
M T
MT
Nieto Lopez
O
O
D000475:Alkenes / Q000138:chemical synthesis* / Q000494:pharmacology; D000480:Alkynes / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001921:Brain / Q000201:enzymology; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D066298:In Vitro Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008744:Methylamines / Q000138:chemical synthesis / Q000494:pharmacology; D008928:Mitochondria / Q000201:enzymology; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis*
D000475:Alkenes; D000480:Alkynes; D007211:Indoles; D008744:Methylamines; D008996:Monoamine Oxidase Inhibitors