Inhibitors of Phenylalanine Ammonia-Lyase (PAL): Synthesis and Biological Evaluation of 5-Substituted 2-Aminoindane-2-phosphonic Acids

✍ Scribed by Jerzy Zoń; Piotr Miziak; Nikolaus Amrhein; Roman Gancarz

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 109 KB
• Volume: 2
• Category: Article
• ISSN: 1612-1872
• DOI: 10.1002/cbdv.200590089

✦ Synopsis

A series of 5-substituted derivatives of the potent phenylalanine ammonia-lyase (PAL) inhibitor 2aminoindane-2-phosphonic acid (AIP; 2) were synthesized. The AIP analogues 3 ± 7, with additional NO 2 , NH 2 , Me, Br, and OH groups, respectively, were tested as in vitro inhibitors of buckwheat PAL, and as in vivo inhibitors of anthocyanin biosynthesis. Within this series, the racemic 5-bromo (6) and 5-methyl (7) congeners were biologically most active (Table ), although being ca. one order of magnitude less potent than AIP proper.