82817-65-0Relevant articles and documents
Nicotinic acid adenine dinucleotide phosphate analogues substituted on the nicotinic acid and adenine ribosides. Effects on receptormediated Ca2+ release
Trabbic, Christopher J.,Zhang, Fan,Walseth, Timothy F.,Slama, James T.
, p. 3593 - 3610 (2015/05/05)
Nicotinic acid adenine dinucleotide phosphate (NAADP) is a Ca2+ releasing intracellular second messenger in both mammals and echinoderms. We report that large functionalized substituents introduced at the nicotinic acid 5-position are recognize
Hydroxy- and amino-substituted piperidinecarboxylic acids as γ-aminobutyric acid agonists and uptake inhibitors
Jacobsen,Labouta,Schaumburg,Falch,Krogsgaard-Larsen
, p. 1157 - 1162 (2007/10/02)
The syntheses of (3RS, 4RS)-4-hydroxypiperidine-3-carboxylic acid (4), (3RS, 5SRJ-5-hydroxypiperiden-3-carboxylic acid (20), (3RS, 4SR)-4-acetamidopiperidine-3-carboxylic acid (10), and (3RS, 5SR)-5-acetamidopiperidine-3-carboxylic acid (18), related to the specific γ-aminobutyric (GABA) uptake inhibitors (RS)-piperidine-3-carboxylic acid (nipecotic acid) and (3RS, 4SR)-4-hydroxypiperidine-3-carboxylic acid (21), are described. Furthermore, (3RS, 4SR)-3-hydroxypiperidine-4-carboxylic acid (14), related to the specific GABA agonist piperidine-4-carboxylic acid (isonipecotic acid), has been synthesized. The structures of 4, 10, 14, 18, and 20 have been established by 270-MHz 1H NMR spectroscopic analyses. The affinity of the compounds for the GABA receptors and for the neuronal (synaptosomal) GABA uptake system in vitro has been measured. Compound 14 interacts selectively with the GABA receptors but less effectively than isonipecotic acid and the cis-isomer 22. Compounds 4, 18, and 20 are inhibitors of the GABA uptake system, although much weaker than nipecotic acid and (3RS, 4SR)-4-hydroxypiperidine-3-carboxylic acid (21). Compound 10 is inactive in both test systems.