140158-50-5

Basic information

• Product Name: ATPA
• Synonyms: (R,S)-ATPA;(RS)-A-AMINO-3-HYDROXY-5-TERT-BUTYL-4-ISOXAZOLEPROPIONIC ACID;(R,S)-ALPHA-AMINO-3-HYDROXY-5-T-BUTYL-4-ISOXAZOLEPROPIONIC ACID;(RS)-ALPHA-AMINO-3-HYDROXY-5-TERT-BUTYL-4-ISOXAZOLEPROPIONIC ACID;(RS)-2-AMINO-3-(3-HYDROXY-5-TERT-BUTYLISOXAZOL-4-YL)PROPANOIC ACID;ATPA;alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionate;ATP synthase α chain
• CAS NO: 140158-50-5
• Molecular Formula: C10H16N2O4
• Molecular Weight: 228.25
• Mol File: 140158-50-5.mol

Chemical Properties

• Boiling Point: 406.8°Cat760mmHg
• Flash Point: 199.9°C
• Appearance: white/solid
• Density: 1.264g/cm³
• Vapor Pressure: 2.38E-07mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Desiccate at +4°C
• Solubility: DMSO: 10 mg/mL
• PKA: 2.15±0.10(Predicted)
• CAS DataBase Reference: ATPA(CAS DataBase Reference)
• NIST Chemistry Reference: ATPA(140158-50-5)
• EPA Substance Registry System: ATPA(140158-50-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 140158-50-5(Hazardous Substances Data)

Usage

Biological Activity

A selective and potent GluR5 kainate receptor agonist (K i = 4.3 nM), inactive at GluR6 (K i > 1 mM) and only weakly active at AMPA receptors (GluR1-4) and the kainate receptors KA-2 and GluR7 (K i values of 6 - 14 μ M). Also available as part of the Kainate Receptor Tocriset? .

InChI:InChI=1/C10H16N2O4/c1-10(2,3)7-5(8(13)12-16-7)4-6(11)9(14)15/h6H,4,11H2,1-3H3,(H,12,13)(H,14,15)

Upstream product

• 95406-73-8 ethyl α-(ethoxycarbonyl)-α-(acetylamino)-3-methoxy-5-tert-butylisoxazole-4-propionate 
• 192439-92-2 2-Acetylamino-2-(5-tert-butyl-2-methoxymethyl-3-oxo-2,3-dihydro-isoxazol-4-ylmethyl)-malonic acid dimethyl ester 
• 95406-70-5 3-methoxy-4-methyl-5-tert-butylisoxazole 
• 95406-69-2 3-hydroxy-4-methyl-5-tert-butylisoxazole 
• 85515-84-0 ethyl (RS)-2,4,4-trimethyl-3-oxopentanoate 
• 17094-34-7 ethyl pivaloylacetate 
• 192439-80-8 4-bromomethyl-2-methoxymethyl-5-tert-butylisoxazolin-3-one 
• 1027496-30-5 2,4-Bis-bromomethyl-5-tert-butyl-isoxazol-3-one 
• 107403-12-3 3-hydroxy-5-tert-butylisoxazole 
• 252354-20-4 5-tert-butyl-4-chloromethyl-3-methoxyisoxazole 
• 252354-17-9 5-tert-butyl-4-hydroxymethyl-3-methoxyisoxazole 
• 158327-07-2 5-tert-butyl-3-methoxyisoxazole-4-carbaldehyde 

Relevant articles and documents

Synthesis of deuterium and tritium labelled (RS)-2-amino-3-(5-tert-butyl-3-hydroxy-4-isosazolyl)propionic acid (ATPA), a selective kainic acid receptor agonist

(RS)-2-Amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA) is an excitatory amino acid receptor agonist showing selectivity for the kainic acid receptor subtype GluR5. As part of the pharmacological characterization of GluR5 receptors, we now report the synthesis of [3H]ATPA based on a four-step synthesis using 5-tert-butyl-3-methoxy-4-isoxazolylcarbaldehyde as the starting material. Using this synthetic procedure deuterium and tritium labelled ATPA have been prepared. [3H]ATPA, with a specific activity of 17 Ci/mmol, was obtained with a radiochemical purity of 98.9%. Attempts to demonstrate specific binding of [3H]ATPA under conventional rat brain membrane receptor binding conditions were unsuccessful.

Excitatory amino-acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid.

We have previously proposed the existence of a lipophilic cavity of the 2-amino-3-(3 -hydroxy-5 -methylisoxazol-4-yl)propionic acid (AMPA) receptor recognition site capable of accommodating alkyl substituents of limited size in the 5-position of the isoxazole ring. In order to indirectly elucidate the approximate extent of this proposed cavity we have synthesized and pharmacologically characterized a number of AMPA analogues. For most of these AMPA analogues, a positive correlation between AMPA receptor affinity and agonist effect was observed. The only exception was demethyl-AMPA (8a), which showed relatively high AMPA receptor affinity (IC50, = 0.27 μM) but remarkably weak agonist potency (EC50 = 900 μM). Whereas the ethyl analogue of AMPA (Et-AMPA) (IC50 = 0.030 μM; EC50 = 2.3 μM) has previously been shown to be slightly more potent than AMPA (IC50 = 0.040 μM; EC50 = 3.5 μM), substitutions of a propyl or a butyl group for the methyl group of AMPA to give 8b IC50 = 0.090 μM; EC50 = 5.0 μM) or 8f (IC50 = 1.0 μM; EC50 = 32 μM), respectively, result in progressive loss of the AMPA agonist effect. Analogues containing larger groups, such as isopentyl (8e), 1-propylbutyl (8g), 2,2-dimethylpropyl (8h), or benzyl (14) groups, were very weak or totally inactive as AMPA receptor ligands.

Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors

The syntheses of (RS)-α-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (α-RS,β-RS)-α-amino-β-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-α-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-α-amino-3-hydroxy-5-isoxazoleval