Inhibitors of phenylalanine ammonia-lyase (PAL): synthesis and biological evaluation of 5-substituted 2-aminoindane-2-phosphonic acids.
A series of 5-substituted derivatives of the potent phenylalanine ammonia-lyase (PAL) inhibitor 2-aminoindane-2-phosphonic acid (AIP; 2) were synthesized. The AIP analogues 3-7, with additional NO2, NH2, 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.
Zoń
Jerzy
J
Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, Wybrzeze Wyspiańskiego 27, PL-50-370 Wrocław. jerzy.zon@pwr.wroc.pl
Miziak
Piotr
P
Amrhein
Nikolaus
N
Gancarz
Roman
R
D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology*; D010650:Phenylalanine Ammonia-Lyase / Q000037:antagonists & inhibitors*
D063065:Organophosphonates; D010650:Phenylalanine Ammonia-Lyase