Albers, Harald M. H. G.; Hendrickx, Loes J. D.; van Tol, Rob J. P.; Hausmann, Jens; Perrakis, Anastassis; Ovaa, Huib published an article in Journal of Medicinal Chemistry. The title of the article was 《Structure-Based Design of Novel Boronic Acid-Based Inhibitors of Autotaxin》.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The author mentioned the following in the article:
Autotaxin (ATX) is a secreted phosphodiesterase that hydrolyzes the abundant phospholipid lysophosphatidylcholine (LPC) to produce lysophosphatidic acid (LPA). The ATX-LPA signaling axis has been implicated in inflammation, fibrosis, and tumor progression, rendering ATX an attractive drug target. We recently described a boronic acid-based inhibitor of ATX, named HA155 (1). Here, we report the design of new inhibitors based on the crystal structure of ATX in complex with inhibitor 1. Furthermore, we describe the syntheses and activities of these new inhibitors, whose potencies can be explained by structural data. To understand the difference in activity between two different isomers with nanomolar potencies, we performed mol. docking experiments Intriguingly, mol. docking suggested a remarkable binding pose for one of the isomers, which differs from the original binding pose of inhibitor 1 for ATX, opening further options for inhibitor design. In the part of experimental materials, we found many familiar compounds, such as (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)
(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.
Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem