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Inhibitors of Phenylalanine Ammonia-Lyase: 2-Aminoindan-2-phosphonic Acid and Related Compounds

✍ Scribed by Zoń, Jerzy ;Amrhein, Nikolaus

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
455 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

2‐Aminoindan‐2‐phosphonic acid (3) was synthesized for the first time both directly from 2‐indanone (7) as well as by alkylation of ethyl diethoxyphosphorylacetate with 1,2‐bis(bromomethyl)benzene (9) via 10–12, respectively. 2‐Hydroxyindan‐2‐phosphonic acid (5) was obtained also from 7 via its diisopropyl ester 8. Compound 3 was found to be a potent inhibitor of the plant enzyme phenylalanine ammonia‐lyase (EC 4.3.1.5) both in vitro and in vivo. Of the related 2‐aminoindan‐2‐carboxylic acid (4), compound 5, and 1‐aminocyclopentylphosphonic acid (6), only 4 inhibited the enzyme but was far less inhibitory than 3.

📜 SIMILAR VOLUMES

Inhibitors of Phenylalanine Ammonia-Lyas
Inhibitors of Phenylalanine Ammonia-Lyase (PAL): Synthesis and Biological Evaluation of 5-Substituted 2-Aminoindane-2-phosphonic Acids
✍ Jerzy Zoń; Piotr Miziak; Nikolaus Amrhein; Roman Gancarz 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 English ⚖ 109 KB

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, a